Merge branch 'master' of https://github.com/python-discord/bot into help-refactor

 Conflicts:

	bot/cogs/help.py

108 files changed, 7258 insertions, 3174 deletions

diff --git a/.coveragerc b/.coveragerc
new file mode 100644
index 000000000..d572bd705
--- /dev/null
+++ b/.coveragerc
@@ -0,0 +1,5 @@
+[run]
+branch = true
+source =
+    bot
+    tests
diff --git a/.github/CODEOWNERS b/.github/CODEOWNERS
new file mode 100644
index 000000000..cf5f1590d
--- /dev/null
+++ b/.github/CODEOWNERS
@@ -0,0 +1 @@
+* @python-discord/core-developers
diff --git a/.gitignore b/.gitignore
index a191523b6..fb3156ab1 100644
--- a/.gitignore
+++ b/.gitignore
@@ -114,8 +114,8 @@ log.*
 # Custom user configuration
 config.yml
 
-# JUnit XML reports from pytest
-junit.xml
+# xmlrunner unittest XML reports
+TEST-**.xml
 
 # Mac OS .DS_Store, which is a file that stores custom attributes of its containing folder
 .DS_Store
diff --git a/Pipfile b/Pipfile
index 82847b23f..7fd3efae8 100644
--- a/Pipfile
+++ b/Pipfile
@@ -4,7 +4,7 @@ verify_ssl = true
 name = "pypi"
 
 [packages]
-discord-py = "~=1.2"
+discord-py = "~=1.3.1"
 aiodns = "~=2.0"
 logmatic-python = "~=0.1"
 aiohttp = "~=3.5"
@@ -21,6 +21,7 @@ more_itertools = "~=7.2"
 urllib3 = ">=1.24.2,<1.25"
 
 [dev-packages]
+coverage = "~=4.5"
 flake8 = "~=3.7"
 flake8-annotations = "~=1.1"
 flake8-bugbear = "~=19.8"
@@ -31,9 +32,8 @@ flake8-tidy-imports = "~=2.0"
 flake8-todo = "~=0.7"
 pre-commit = "~=1.18"
 safety = "~=1.8"
+unittest-xml-reporting = "~=2.5"
 dodgy = "~=0.1"
-pytest = "~=5.1"
-pytest-cov = "~=2.7"
 
 [requires]
 python_version = "3.7"
@@ -44,3 +44,5 @@ lint = "python -m flake8"
 precommit = "pre-commit install"
 build = "docker build -t pythondiscord/bot:latest -f Dockerfile ."
 push = "docker push pythondiscord/bot:latest"
+test = "coverage run -m unittest"
+report = "coverage report"
diff --git a/Pipfile.lock b/Pipfile.lock
index 4e6b4eaf8..bf8ff47e9 100644
--- a/Pipfile.lock
+++ b/Pipfile.lock
@@ -1,7 +1,7 @@
 {
     "_meta": {
         "hash": {
-            "sha256": "c2537cc3c5b0886d0b38f9b48f4f4b93e1e74d925454aa71a2189bddedadde42"
+            "sha256": "0a0354a8cbd25b19c61b68f928493a445e737dc6447c97f4c4b52fbf72d887ac"
         },
         "pipfile-spec": 6,
         "requires": {
@@ -18,11 +18,11 @@
     "default": {
         "aio-pika": {
             "hashes": [
-                "sha256:29f27a8092169924c9eefb0c5e428d216706618dc9caa75ddb7759638e16cf26",
-                "sha256:4f77ba9b6e7bc27fc88c49638bc3657ae5d4a2539e17fa0c2b25b370547b1b50"
+                "sha256:a5837277e53755078db3a9e8c45bbca605c8ba9ecba7a02d74a7a1779f444723",
+                "sha256:fa32e33b4b7d0804dcf439ae6ff24d2f0a83d1ba280ee9f555e647d71d394ff5"
             ],
             "index": "pypi",
-            "version": "==6.1.2"
+            "version": "==6.4.1"
         },
         "aiodns": {
             "hashes": [
@@ -34,38 +34,28 @@
         },
         "aiohttp": {
             "hashes": [
-                "sha256:00d198585474299c9c3b4f1d5de1a576cc230d562abc5e4a0e81d71a20a6ca55",
-                "sha256:0155af66de8c21b8dba4992aaeeabf55503caefae00067a3b1139f86d0ec50ed",
-                "sha256:09654a9eca62d1bd6d64aa44db2498f60a5c1e0ac4750953fdd79d5c88955e10",
-                "sha256:199f1d106e2b44b6dacdf6f9245493c7d716b01d0b7fbe1959318ba4dc64d1f5",
-                "sha256:296f30dedc9f4b9e7a301e5cc963012264112d78a1d3094cd83ef148fdf33ca1",
-                "sha256:368ed312550bd663ce84dc4b032a962fcb3c7cae099dbbd48663afc305e3b939",
-                "sha256:40d7ea570b88db017c51392349cf99b7aefaaddd19d2c78368aeb0bddde9d390",
-                "sha256:629102a193162e37102c50713e2e31dc9a2fe7ac5e481da83e5bb3c0cee700aa",
-                "sha256:6d5ec9b8948c3d957e75ea14d41e9330e1ac3fed24ec53766c780f82805140dc",
-                "sha256:87331d1d6810214085a50749160196391a712a13336cd02ce1c3ea3d05bcf8d5",
-                "sha256:9a02a04bbe581c8605ac423ba3a74999ec9d8bce7ae37977a3d38680f5780b6d",
-                "sha256:9c4c83f4fa1938377da32bc2d59379025ceeee8e24b89f72fcbccd8ca22dc9bf",
-                "sha256:9cddaff94c0135ee627213ac6ca6d05724bfe6e7a356e5e09ec57bd3249510f6",
-                "sha256:a25237abf327530d9561ef751eef9511ab56fd9431023ca6f4803f1994104d72",
-                "sha256:a5cbd7157b0e383738b8e29d6e556fde8726823dae0e348952a61742b21aeb12",
-                "sha256:a97a516e02b726e089cffcde2eea0d3258450389bbac48cbe89e0f0b6e7b0366",
-                "sha256:acc89b29b5f4e2332d65cd1b7d10c609a75b88ef8925d487a611ca788432dfa4",
-                "sha256:b05bd85cc99b06740aad3629c2585bda7b83bd86e080b44ba47faf905fdf1300",
-                "sha256:c2bec436a2b5dafe5eaeb297c03711074d46b6eb236d002c13c42f25c4a8ce9d",
-                "sha256:cc619d974c8c11fe84527e4b5e1c07238799a8c29ea1c1285149170524ba9303",
-                "sha256:d4392defd4648badaa42b3e101080ae3313e8f4787cb517efd3f5b8157eaefd6",
-                "sha256:e1c3c582ee11af7f63a34a46f0448fca58e59889396ffdae1f482085061a2889"
+                "sha256:1e984191d1ec186881ffaed4581092ba04f7c61582a177b187d3a2f07ed9719e",
+                "sha256:259ab809ff0727d0e834ac5e8a283dc5e3e0ecc30c4d80b3cd17a4139ce1f326",
+                "sha256:2f4d1a4fdce595c947162333353d4a44952a724fba9ca3205a3df99a33d1307a",
+                "sha256:32e5f3b7e511aa850829fbe5aa32eb455e5534eaa4b1ce93231d00e2f76e5654",
+                "sha256:344c780466b73095a72c616fac5ea9c4665add7fc129f285fbdbca3cccf4612a",
+                "sha256:460bd4237d2dbecc3b5ed57e122992f60188afe46e7319116da5eb8a9dfedba4",
+                "sha256:4c6efd824d44ae697814a2a85604d8e992b875462c6655da161ff18fd4f29f17",
+                "sha256:50aaad128e6ac62e7bf7bd1f0c0a24bc968a0c0590a726d5a955af193544bcec",
+                "sha256:6206a135d072f88da3e71cc501c59d5abffa9d0bb43269a6dcd28d66bfafdbdd",
+                "sha256:65f31b622af739a802ca6fd1a3076fd0ae523f8485c52924a89561ba10c49b48",
+                "sha256:ae55bac364c405caa23a4f2d6cfecc6a0daada500274ffca4a9230e7129eac59",
+                "sha256:b778ce0c909a2653741cb4b1ac7015b5c130ab9c897611df43ae6a58523cb965"
             ],
             "index": "pypi",
-            "version": "==3.5.4"
+            "version": "==3.6.2"
         },
         "aiormq": {
             "hashes": [
-                "sha256:c3e4dd01a2948a75f739fb637334dbb8c6f1a4cecf74d5ed662dc3bab7f39973",
-                "sha256:e220d3f9477bb2959b729b79bec815148ddb8a7686fc6c3d05d41c88ebd7c59e"
+                "sha256:8c215a970133ab5ee7c478decac55b209af7731050f52d11439fe910fa0f9e9d",
+                "sha256:9210f3389200aee7d8067f6435f4a9eff2d3a30b88beb5eaae406ccc11c0fc01"
             ],
-            "version": "==2.8.0"
+            "version": "==3.2.0"
         },
         "alabaster": {
             "hashes": [
@@ -83,65 +73,65 @@
         },
         "attrs": {
             "hashes": [
-                "sha256:69c0dbf2ed392de1cb5ec704444b08a5ef81680a61cb899dc08127123af36a79",
-                "sha256:f0b870f674851ecbfbbbd364d6b5cbdff9dcedbc7f3f5e18a6891057f21fe399"
+                "sha256:08a96c641c3a74e44eb59afb61a24f2cb9f4d7188748e76ba4bb5edfa3cb7d1c",
+                "sha256:f7b7ce16570fe9965acd6d30101a28f62fb4a7f9e926b3bbc9b61f8b04247e72"
             ],
-            "version": "==19.1.0"
+            "version": "==19.3.0"
         },
         "babel": {
             "hashes": [
-                "sha256:af92e6106cb7c55286b25b38ad7695f8b4efb36a90ba483d7f7a6628c46158ab",
-                "sha256:e86135ae101e31e2c8ec20a4e0c5220f4eed12487d5cf3f78be7e98d3a57fc28"
+                "sha256:1aac2ae2d0d8ea368fa90906567f5c08463d98ade155c0c4bfedd6a0f7160e38",
+                "sha256:d670ea0b10f8b723672d3a6abeb87b565b244da220d76b4dba1b66269ec152d4"
             ],
-            "version": "==2.7.0"
+            "version": "==2.8.0"
         },
         "beautifulsoup4": {
             "hashes": [
-                "sha256:05668158c7b85b791c5abde53e50265e16f98ad601c402ba44d70f96c4159612",
-                "sha256:25288c9e176f354bf277c0a10aa96c782a6a18a17122dba2e8cec4a97e03343b",
-                "sha256:f040590be10520f2ea4c2ae8c3dae441c7cfff5308ec9d58a0ec0c1b8f81d469"
+                "sha256:05fd825eb01c290877657a56df4c6e4c311b3965bda790c613a3d6fb01a5462a",
+                "sha256:9fbb4d6e48ecd30bcacc5b63b94088192dcda178513b2ae3c394229f8911b887",
+                "sha256:e1505eeed31b0f4ce2dbb3bc8eb256c04cc2b3b72af7d551a4ab6efd5cbe5dae"
             ],
-            "version": "==4.8.0"
+            "version": "==4.8.2"
         },
         "certifi": {
             "hashes": [
-                "sha256:e4f3620cfea4f83eedc95b24abd9cd56f3c4b146dd0177e83a21b4eb49e21e50",
-                "sha256:fd7c7c74727ddcf00e9acd26bba8da604ffec95bf1c2144e67aff7a8b50e6cef"
+                "sha256:017c25db2a153ce562900032d5bc68e9f191e44e9a0f762f373977de9df1fbb3",
+                "sha256:25b64c7da4cd7479594d035c08c2d809eb4aab3a26e5a990ea98cc450c320f1f"
             ],
-            "version": "==2019.9.11"
+            "version": "==2019.11.28"
         },
         "cffi": {
             "hashes": [
-                "sha256:041c81822e9f84b1d9c401182e174996f0bae9991f33725d059b771744290774",
-                "sha256:046ef9a22f5d3eed06334d01b1e836977eeef500d9b78e9ef693f9380ad0b83d",
-                "sha256:066bc4c7895c91812eff46f4b1c285220947d4aa46fa0a2651ff85f2afae9c90",
-                "sha256:066c7ff148ae33040c01058662d6752fd73fbc8e64787229ea8498c7d7f4041b",
-                "sha256:2444d0c61f03dcd26dbf7600cf64354376ee579acad77aef459e34efcb438c63",
-                "sha256:300832850b8f7967e278870c5d51e3819b9aad8f0a2c8dbe39ab11f119237f45",
-                "sha256:34c77afe85b6b9e967bd8154e3855e847b70ca42043db6ad17f26899a3df1b25",
-                "sha256:46de5fa00f7ac09f020729148ff632819649b3e05a007d286242c4882f7b1dc3",
-                "sha256:4aa8ee7ba27c472d429b980c51e714a24f47ca296d53f4d7868075b175866f4b",
-                "sha256:4d0004eb4351e35ed950c14c11e734182591465a33e960a4ab5e8d4f04d72647",
-                "sha256:4e3d3f31a1e202b0f5a35ba3bc4eb41e2fc2b11c1eff38b362de710bcffb5016",
-                "sha256:50bec6d35e6b1aaeb17f7c4e2b9374ebf95a8975d57863546fa83e8d31bdb8c4",
-                "sha256:55cad9a6df1e2a1d62063f79d0881a414a906a6962bc160ac968cc03ed3efcfb",
-                "sha256:5662ad4e4e84f1eaa8efce5da695c5d2e229c563f9d5ce5b0113f71321bcf753",
-                "sha256:59b4dc008f98fc6ee2bb4fd7fc786a8d70000d058c2bbe2698275bc53a8d3fa7",
-                "sha256:73e1ffefe05e4ccd7bcea61af76f36077b914f92b76f95ccf00b0c1b9186f3f9",
-                "sha256:a1f0fd46eba2d71ce1589f7e50a9e2ffaeb739fb2c11e8192aa2b45d5f6cc41f",
-                "sha256:a2e85dc204556657661051ff4bab75a84e968669765c8a2cd425918699c3d0e8",
-                "sha256:a5457d47dfff24882a21492e5815f891c0ca35fefae8aa742c6c263dac16ef1f",
-                "sha256:a8dccd61d52a8dae4a825cdbb7735da530179fea472903eb871a5513b5abbfdc",
-                "sha256:ae61af521ed676cf16ae94f30fe202781a38d7178b6b4ab622e4eec8cefaff42",
-                "sha256:b012a5edb48288f77a63dba0840c92d0504aa215612da4541b7b42d849bc83a3",
-                "sha256:d2c5cfa536227f57f97c92ac30c8109688ace8fa4ac086d19d0af47d134e2909",
-                "sha256:d42b5796e20aacc9d15e66befb7a345454eef794fdb0737d1af593447c6c8f45",
-                "sha256:dee54f5d30d775f525894d67b1495625dd9322945e7fee00731952e0368ff42d",
-                "sha256:e070535507bd6aa07124258171be2ee8dfc19119c28ca94c9dfb7efd23564512",
-                "sha256:e1ff2748c84d97b065cc95429814cdba39bcbd77c9c85c89344b317dc0d9cbff",
-                "sha256:ed851c75d1e0e043cbf5ca9a8e1b13c4c90f3fbd863dacb01c0808e2b5204201"
-            ],
-            "version": "==1.12.3"
+                "sha256:001bf3242a1bb04d985d63e138230802c6c8d4db3668fb545fb5005ddf5bb5ff",
+                "sha256:00789914be39dffba161cfc5be31b55775de5ba2235fe49aa28c148236c4e06b",
+                "sha256:028a579fc9aed3af38f4892bdcc7390508adabc30c6af4a6e4f611b0c680e6ac",
+                "sha256:14491a910663bf9f13ddf2bc8f60562d6bc5315c1f09c704937ef17293fb85b0",
+                "sha256:1cae98a7054b5c9391eb3249b86e0e99ab1e02bb0cc0575da191aedadbdf4384",
+                "sha256:2089ed025da3919d2e75a4d963d008330c96751127dd6f73c8dc0c65041b4c26",
+                "sha256:2d384f4a127a15ba701207f7639d94106693b6cd64173d6c8988e2c25f3ac2b6",
+                "sha256:337d448e5a725bba2d8293c48d9353fc68d0e9e4088d62a9571def317797522b",
+                "sha256:399aed636c7d3749bbed55bc907c3288cb43c65c4389964ad5ff849b6370603e",
+                "sha256:3b911c2dbd4f423b4c4fcca138cadde747abdb20d196c4a48708b8a2d32b16dd",
+                "sha256:3d311bcc4a41408cf5854f06ef2c5cab88f9fded37a3b95936c9879c1640d4c2",
+                "sha256:62ae9af2d069ea2698bf536dcfe1e4eed9090211dbaafeeedf5cb6c41b352f66",
+                "sha256:66e41db66b47d0d8672d8ed2708ba91b2f2524ece3dee48b5dfb36be8c2f21dc",
+                "sha256:675686925a9fb403edba0114db74e741d8181683dcf216be697d208857e04ca8",
+                "sha256:7e63cbcf2429a8dbfe48dcc2322d5f2220b77b2e17b7ba023d6166d84655da55",
+                "sha256:8a6c688fefb4e1cd56feb6c511984a6c4f7ec7d2a1ff31a10254f3c817054ae4",
+                "sha256:8c0ffc886aea5df6a1762d0019e9cb05f825d0eec1f520c51be9d198701daee5",
+                "sha256:95cd16d3dee553f882540c1ffe331d085c9e629499ceadfbda4d4fde635f4b7d",
+                "sha256:99f748a7e71ff382613b4e1acc0ac83bf7ad167fb3802e35e90d9763daba4d78",
+                "sha256:b8c78301cefcf5fd914aad35d3c04c2b21ce8629b5e4f4e45ae6812e461910fa",
+                "sha256:c420917b188a5582a56d8b93bdd8e0f6eca08c84ff623a4c16e809152cd35793",
+                "sha256:c43866529f2f06fe0edc6246eb4faa34f03fe88b64a0a9a942561c8e22f4b71f",
+                "sha256:cab50b8c2250b46fe738c77dbd25ce017d5e6fb35d3407606e7a4180656a5a6a",
+                "sha256:cef128cb4d5e0b3493f058f10ce32365972c554572ff821e175dbc6f8ff6924f",
+                "sha256:cf16e3cf6c0a5fdd9bc10c21687e19d29ad1fe863372b5543deaec1039581a30",
+                "sha256:e56c744aa6ff427a607763346e4170629caf7e48ead6921745986db3692f987f",
+                "sha256:e577934fc5f8779c554639376beeaa5657d54349096ef24abe8c74c5d9c117c3",
+                "sha256:f2b0fa0c01d8a0c7483afd9f31d7ecf2d71760ca24499c8697aeb5ca37dc090c"
+            ],
+            "version": "==1.14.0"
         },
         "chardet": {
             "hashes": [
@@ -150,35 +140,27 @@
             ],
             "version": "==3.0.4"
         },
-        "colorama": {
-            "hashes": [
-                "sha256:05eed71e2e327246ad6b38c540c4a3117230b19679b875190486ddd2d721422d",
-                "sha256:f8ac84de7840f5b9c4e3347b3c1eaa50f7e49c2b07596221daec5edaabbd7c48"
-            ],
-            "version": "==0.4.1"
-        },
         "deepdiff": {
             "hashes": [
-                "sha256:1123762580af0904621136d117c8397392a244d3ff0fa0a50de57a7939582476",
-                "sha256:6ab13e0cbb627dadc312deaca9bef38de88a737a9bbdbfbe6e3857748219c127"
+                "sha256:b3fa588d1eac7fa318ec1fb4f2004568e04cb120a1989feda8e5e7164bcbf07a",
+                "sha256:ed7342d3ed3c0c2058a3fb05b477c943c9959ef62223dca9baa3375718a25d87"
             ],
             "index": "pypi",
-            "version": "==4.0.7"
+            "version": "==4.2.0"
         },
         "discord-py": {
             "hashes": [
-                "sha256:4684733fa137cc7def18087ae935af615212e423e3dbbe3e84ef01d7ae8ed17d"
+                "sha256:8bfe5628d31771744000f19135c386c74ac337479d7282c26cc1627b9d31f360"
             ],
             "index": "pypi",
-            "version": "==1.2.3"
+            "version": "==1.3.1"
         },
         "docutils": {
             "hashes": [
-                "sha256:6c4f696463b79f1fb8ba0c594b63840ebd41f059e92b31957c46b74a4599b6d0",
-                "sha256:9e4d7ecfc600058e07ba661411a2b7de2fd0fafa17d1a7f7361cd47b1175c827",
-                "sha256:a2aeea129088da402665e92e0b25b04b073c04b2dce4ab65caaa38b7ce2e1a99"
+                "sha256:0c5b78adfbf7762415433f5515cd5c9e762339e23369dbe8000d84a4bf4ab3af",
+                "sha256:c2de3a60e9e7d07be26b7f2b00ca0309c207e06c100f9cc2a94931fc75a478fc"
             ],
-            "version": "==0.15.2"
+            "version": "==0.16"
         },
         "fuzzywuzzy": {
             "hashes": [
@@ -197,24 +179,17 @@
         },
         "imagesize": {
             "hashes": [
-                "sha256:3f349de3eb99145973fefb7dbe38554414e5c30abd0c8e4b970a7c9d09f3a1d8",
-                "sha256:f3832918bc3c66617f92e35f5d70729187676313caa60c187eb0f28b8fe5e3b5"
+                "sha256:6965f19a6a2039c7d48bca7dba2473069ff854c36ae6f19d2cde309d998228a1",
+                "sha256:b1f6b5a4eab1f73479a50fb79fcf729514a900c341d8503d62a62dbc4127a2b1"
             ],
-            "version": "==1.1.0"
+            "version": "==1.2.0"
         },
         "jinja2": {
             "hashes": [
-                "sha256:065c4f02ebe7f7cf559e49ee5a95fb800a9e4528727aec6f24402a5374c65013",
-                "sha256:14dd6caf1527abb21f08f86c784eac40853ba93edb79552aa1e4b8aef1b61c7b"
+                "sha256:93187ffbc7808079673ef52771baa950426fd664d3aad1d0fa3e95644360e250",
+                "sha256:b0eaf100007721b5c16c1fc1eecb87409464edc10469ddc9a22a27a99123be49"
             ],
-            "version": "==2.10.1"
-        },
-        "jsonpickle": {
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-            ],
-            "version": "==1.2"
+            "version": "==2.11.1"
         },
         "logmatic-python": {
             "hashes": [
@@ -225,31 +200,36 @@
         },
         "lxml": {
             "hashes": [
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-                "sha256:c27eaed872185f047bb7f7da2d21a7d8913457678c9a100a50db6da890bc28b9",
-                "sha256:c81cb40bff373ab7a7446d6bbca0190bccc5be3448b47b51d729e37799bb5692",
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-            ],
-            "index": "pypi",
-            "version": "==4.4.1"
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+                "sha256:b4b2c63cc7963aedd08a5f5a454c9f67251b1ac9e22fd9d72836206c42dc2a72",
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+                "sha256:d5b3c4b7edd2e770375a01139be11307f04341ec709cf724e0f26ebb1eef12c3",
+                "sha256:deadf4df349d1dcd7b2853a2c8796593cc346600726eff680ed8ed11812382a7",
+                "sha256:df533af6f88080419c5a604d0d63b2c33b1c0c4409aba7d0cb6de305147ea8c8",
+                "sha256:e4aa948eb15018a657702fee0b9db47e908491c64d36b4a90f59a64741516e77",
+                "sha256:e5d842c73e4ef6ed8c1bd77806bf84a7cb535f9c0cf9b2c74d02ebda310070e1",
+                "sha256:ebec08091a22c2be870890913bdadd86fcd8e9f0f22bcb398abd3af914690c15",
+                "sha256:edc15fcfd77395e24543be48871c251f38132bb834d9fdfdad756adb6ea37679",
+                "sha256:f2b74784ed7e0bc2d02bd53e48ad6ba523c9b36c194260b7a5045071abbb1012",
+                "sha256:fa071559f14bd1e92077b1b5f6c22cf09756c6de7139370249eb372854ce51e6",
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+                "sha256:fe976a0f1ef09b3638778024ab9fb8cde3118f203364212c198f71341c0715ca"
+            ],
+            "index": "pypi",
+            "version": "==4.5.0"
         },
         "markdownify": {
             "hashes": [
@@ -264,13 +244,16 @@
                 "sha256:09027a7803a62ca78792ad89403b1b7a73a01c8cb65909cd876f7fcebd79b161",
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                 "sha256:1027c282dad077d0bae18be6794e6b6b8c91d58ed8a8d89a89d59693b9131db5",
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                 "sha256:535f6fc4d397c1563d08b88e485c3496cf5784e927af890fb3c3aac7f933ec66",
+                "sha256:596510de112c685489095da617b5bcbbac7dd6384aeebeda4df6025d0256a81b",
                 "sha256:62fe6c95e3ec8a7fad637b7f3d372c15ec1caa01ab47926cfdf7a75b40e0eac1",
+                "sha256:6788b695d50a51edb699cb55e35487e430fa21f1ed838122d722e0ff0ac5ba15",
                 "sha256:6dd73240d2af64df90aa7c4e7481e23825ea70af4b4922f8ede5b9e35f78a3b1",
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                 "sha256:79855e1c5b8da654cf486b830bd42c06e8780cea587384cf6545b7d9ac013a0b",
@@ -287,7 +270,9 @@
                 "sha256:ba59edeaa2fc6114428f1637ffff42da1e311e29382d81b339c1817d37ec93c6",
                 "sha256:c8716a48d94b06bb3b2524c2b77e055fb313aeb4ea620c8dd03a105574ba704f",
                 "sha256:cd5df75523866410809ca100dc9681e301e3c27567cf498077e8551b6d20e42f",
-                "sha256:e249096428b3ae81b08327a63a485ad0878de3fb939049038579ac0ef61e17e7"
+                "sha256:cdb132fc825c38e1aeec2c8aa9338310d29d337bebbd7baa06889d09a60a1fa2",
+                "sha256:e249096428b3ae81b08327a63a485ad0878de3fb939049038579ac0ef61e17e7",
+                "sha256:e8313f01ba26fbbe36c7be1966a7b7424942f670f38e666995b88d012765b9be"
             ],
             "version": "==1.1.1"
         },
@@ -301,37 +286,25 @@
         },
         "multidict": {
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-                "sha256:db603a1c235d110c860d5f39988ebc8218ee028f07a7cbc056ba6424372ca31b"
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-            "version": "==4.5.2"
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+                "sha256:9a7b115ee0b9b92d10ebc246811d8f55d0c57e82dbb6a26b23c9a9a6ad40ce0c",
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+                "sha256:f29b885e4903bd57a7789f09fe9d60b6475a6c1a4c0eca874d8558f00f9d4b51"
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+            "version": "==4.7.4"
         },
         "ordered-set": {
             "hashes": [
@@ -341,10 +314,10 @@
         },
         "packaging": {
             "hashes": [
-                "sha256:28b924174df7a2fa32c1953825ff29c61e2f5e082343165438812f00d3a7fc47",
-                "sha256:d9551545c6d761f3def1677baf08ab2a3ca17c56879e70fecba2fc4dde4ed108"
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             ],
-            "version": "==19.2"
+            "version": "==20.1"
         },
         "pamqp": {
             "hashes": [
@@ -355,21 +328,37 @@
         },
         "pycares": {
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-            "version": "==3.0.0"
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+                "sha256:9a0a1845f8cb2e62332bca0aaa9ad5494603ac43fb60d510a61d5b5b170d7216",
+                "sha256:a05bbfdfd41f8410a905a818f329afe7510cbd9ee65c60f8860a72b6c64ce5dc",
+                "sha256:a5089fd660f0b0d228b14cdaa110d0d311edfa5a63f800618dbf1321dcaef66b",
+                "sha256:c457a709e6f2befea7e2996c991eda6d79705dd075f6521593ba6ebc1485b811",
+                "sha256:c5cb72644b04e5e5abfb1e10a0e7eb75da6684ea0e60871652f348e412cf3b11",
+                "sha256:cce46dd4717debfd2aab79d6d7f0cbdf6b1e982dc4d9bebad81658d59ede07c2",
+                "sha256:cfdd1f90bcf373b00f4b2c55ea47868616fe2f779f792fc913fa82a3d64ffe43",
+                "sha256:d88a279cbc5af613f73e86e19b3f63850f7a2e2736e249c51995dedcc830b1bb",
+                "sha256:eba9a9227438da5e78fc8eee32f32eb35d9a50cf0a0bd937eb6275c7cc3015fe",
+                "sha256:eee7b6a5f5b5af050cb7d66ab28179287b416f06d15a8974ac831437fec51336",
+                "sha256:f41ac1c858687e53242828c9f59c2e7b0b95dbcd5bdd09c7e5d3c48b0f89a25a",
+                "sha256:f8deaefefc3a589058df1b177275f79233e8b0eeee6734cf4336d80164ecd022",
+                "sha256:fa78e919f3bd7d6d075db262aa41079b4c02da315c6043c6f43881e2ebcdd623",
+                "sha256:fadb97d2e02dabdc15a0091591a972a938850d79ddde23d385d813c1731983f0"
+            ],
+            "version": "==3.1.1"
         },
         "pycparser": {
             "hashes": [
@@ -379,25 +368,25 @@
         },
         "pygments": {
             "hashes": [
-                "sha256:71e430bc85c88a430f000ac1d9b331d2407f681d6f6aec95e8bcfbc3df5b0127",
-                "sha256:881c4c157e45f30af185c1ffe8d549d48ac9127433f2c380c24b84572ad66297"
+                "sha256:2a3fe295e54a20164a9df49c75fa58526d3be48e14aceba6d6b1e8ac0bfd6f1b",
+                "sha256:98c8aa5a9f778fcd1026a17361ddaf7330d1b7c62ae97c3bb0ae73e0b9b6b0fe"
             ],
-            "version": "==2.4.2"
+            "version": "==2.5.2"
         },
         "pyparsing": {
             "hashes": [
-                "sha256:6f98a7b9397e206d78cc01df10131398f1c8b8510a2f4d97d9abd82e1aacdd80",
-                "sha256:d9338df12903bbf5d65a0e4e87c2161968b10d2e489652bb47001d82a9b028b4"
+                "sha256:4c830582a84fb022400b85429791bc551f1f4871c33f23e44f353119e92f969f",
+                "sha256:c342dccb5250c08d45fd6f8b4a559613ca603b57498511740e65cd11a2e7dcec"
             ],
-            "version": "==2.4.2"
+            "version": "==2.4.6"
         },
         "python-dateutil": {
             "hashes": [
-                "sha256:7e6584c74aeed623791615e26efd690f29817a27c73085b78e4bad02493df2fb",
-                "sha256:c89805f6f4d64db21ed966fda138f8a5ed7a4fdbc1a8ee329ce1b74e3c74da9e"
+                "sha256:73ebfe9dbf22e832286dafa60473e4cd239f8592f699aa5adaf10050e6e1823c",
+                "sha256:75bb3f31ea686f1197762692a9ee6a7550b59fc6ca3a1f4b5d7e32fb98e2da2a"
             ],
             "index": "pypi",
-            "version": "==2.8.0"
+            "version": "==2.8.1"
         },
         "python-json-logger": {
             "hashes": [
@@ -407,29 +396,27 @@
         },
         "pytz": {
             "hashes": [
-                "sha256:26c0b32e437e54a18161324a2fca3c4b9846b74a8dccddd843113109e1116b32",
-                "sha256:c894d57500a4cd2d5c71114aaab77dbab5eabd9022308ce5ac9bb93a60a6f0c7"
+                "sha256:1c557d7d0e871de1f5ccd5833f60fb2550652da6be2693c1e02300743d21500d",
+                "sha256:b02c06db6cf09c12dd25137e563b31700d3b80fcc4ad23abb7a315f2789819be"
             ],
-            "version": "==2019.2"
+            "version": "==2019.3"
         },
         "pyyaml": {
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-                "sha256:f81025eddd0327c7d4cfe9b62cf33190e1e736cc6e97502b3ec425f574b3e7a8"
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+                "sha256:1cf708e2ac57f3aabc87405f04b86354f66799c8e62c28c5fc5f88b5521b2dbf",
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+                "sha256:4fee71aa5bc6ed9d5f116327c04273e25ae31a3020386916905767ec4fc5317e",
+                "sha256:70024e02197337533eef7b85b068212420f950319cc8c580261963aefc75f811",
+                "sha256:74782fbd4d4f87ff04159e986886931456a1894c61229be9eaf4de6f6e44b99e",
+                "sha256:940532b111b1952befd7db542c370887a8611660d2b9becff75d39355303d82d",
+                "sha256:cb1f2f5e426dc9f07a7681419fe39cee823bb74f723f36f70399123f439e9b20",
+                "sha256:dbbb2379c19ed6042e8f11f2a2c66d39cceb8aeace421bfc29d085d93eda3689",
+                "sha256:e3a057b7a64f1222b56e47bcff5e4b94c4f61faac04c7c4ecb1985e18caa3994",
+                "sha256:e9f45bd5b92c7974e59bcd2dcc8631a6b6cc380a904725fce7bc08872e691615"
             ],
             "index": "pypi",
-            "version": "==5.1.2"
+            "version": "==5.3"
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         "requests": {
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@@ -441,31 +428,32 @@
         },
         "six": {
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-                "sha256:3350809f0555b11f552448330d0b52d5f24c91a322ea4a15ef22629740f3761c",
-                "sha256:d16a0141ec1a18405cd4ce8b4613101da75da0e9a7aec5bdd4fa804d0e0eba73"
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-            "version": "==1.12.0"
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             "hashes": [
-                "sha256:713e53b79cbcf97bc5245a06080a33d54a77e7cce2f789c835a143bcdb5c033e"
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-            "version": "==1.9.1"
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         "soupsieve": {
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-                "sha256:b91d676b330a0ebd5b21719cb6e9b57c57d433671f65b9c28dd3461d9a1ed0b6"
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-            "version": "==1.9.4"
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         "sphinx": {
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         "sphinxcontrib-applehelp": {
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@@ -519,45 +507,52 @@
         },
         "websockets": {
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-            "version": "==6.0"
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         "yarl": {
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+                "sha256:a161de7e50224e8e3de6e184707476b5a989037dcb24292b391a3d66ff158e70",
+                "sha256:a4844ebb2be14768f7994f2017f70aca39d658a96c786211be5ddbe1c68794c1",
+                "sha256:c2b509ac3d4b988ae8769901c66345425e361d518aecbe4acbfc2567e416626a",
+                "sha256:c9959d49a77b0e07559e579f38b2f3711c2b8716b8410b320bf9713013215a1b",
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+                "sha256:e15199cdb423316e15f108f51249e44eb156ae5dba232cb73be555324a1d49c2"
+            ],
+            "version": "==1.4.2"
         }
     },
     "develop": {
@@ -568,26 +563,19 @@
             ],
             "version": "==1.3.0"
         },
-        "atomicwrites": {
-            "hashes": [
-                "sha256:03472c30eb2c5d1ba9227e4c2ca66ab8287fbfbbda3888aa93dc2e28fc6811b4",
-                "sha256:75a9445bac02d8d058d5e1fe689654ba5a6556a1dfd8ce6ec55a0ed79866cfa6"
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-        },
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             "hashes": [
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-                "sha256:f0b870f674851ecbfbbbd364d6b5cbdff9dcedbc7f3f5e18a6891057f21fe399"
+                "sha256:08a96c641c3a74e44eb59afb61a24f2cb9f4d7188748e76ba4bb5edfa3cb7d1c",
+                "sha256:f7b7ce16570fe9965acd6d30101a28f62fb4a7f9e926b3bbc9b61f8b04247e72"
             ],
-            "version": "==19.1.0"
+            "version": "==19.3.0"
         },
         "certifi": {
             "hashes": [
-                "sha256:e4f3620cfea4f83eedc95b24abd9cd56f3c4b146dd0177e83a21b4eb49e21e50",
-                "sha256:fd7c7c74727ddcf00e9acd26bba8da604ffec95bf1c2144e67aff7a8b50e6cef"
+                "sha256:017c25db2a153ce562900032d5bc68e9f191e44e9a0f762f373977de9df1fbb3",
+                "sha256:25b64c7da4cd7479594d035c08c2d809eb4aab3a26e5a990ea98cc450c320f1f"
             ],
-            "version": "==2019.9.11"
+            "version": "==2019.11.28"
         },
         "cfgv": {
             "hashes": [
@@ -610,13 +598,6 @@
             ],
             "version": "==7.0"
         },
-        "colorama": {
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-                "sha256:05eed71e2e327246ad6b38c540c4a3117230b19679b875190486ddd2d721422d",
-                "sha256:f8ac84de7840f5b9c4e3347b3c1eaa50f7e49c2b07596221daec5edaabbd7c48"
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-            "version": "==0.4.1"
-        },
         "coverage": {
             "hashes": [
                 "sha256:08907593569fe59baca0bf152c43f3863201efb6113ecb38ce7e97ce339805a6",
@@ -652,14 +633,16 @@
                 "sha256:fa964bae817babece5aa2e8c1af841bebb6d0b9add8e637548809d040443fee0",
                 "sha256:ff37757e068ae606659c28c3bd0d923f9d29a85de79bf25b2b34b148473b5025"
             ],
+            "index": "pypi",
             "version": "==4.5.4"
         },
         "dodgy": {
             "hashes": [
-                "sha256:65e13cf878d7aff129f1461c13cb5fd1bb6dfe66bb5327e09379c3877763280c"
+                "sha256:28323cbfc9352139fdd3d316fa17f325cc0e9ac74438cbba51d70f9b48f86c3a",
+                "sha256:51f54c0fd886fa3854387f354b19f429d38c04f984f38bc572558b703c0542a6"
             ],
             "index": "pypi",
-            "version": "==0.1.9"
+            "version": "==0.2.1"
         },
         "dparse": {
             "hashes": [
@@ -677,19 +660,19 @@
         },
         "flake8": {
             "hashes": [
-                "sha256:19241c1cbc971b9962473e4438a2ca19749a7dd002dd1a946eaba171b4114548",
-                "sha256:8e9dfa3cecb2400b3738a42c54c3043e821682b9c840b0448c0503f781130696"
+                "sha256:45681a117ecc81e870cbf1262835ae4af5e7a8b08e40b944a8a6e6b895914cfb",
+                "sha256:49356e766643ad15072a789a20915d3c91dc89fd313ccd71802303fd67e4deca"
             ],
             "index": "pypi",
-            "version": "==3.7.8"
+            "version": "==3.7.9"
         },
         "flake8-annotations": {
             "hashes": [
-                "sha256:6ac7ca1e706307686b60af8043ff1db31dc2cfc1233c8210d67a3d9b8f364736",
-                "sha256:b51131007000d67217608fa028a35ff80aa400b474e5972f1f99c2cf9d26bd2e"
+                "sha256:05b85538014c850a86dce7374bb6621c64481c24e35e8e90af1315f4d7a3dbaa",
+                "sha256:43e5233a76fda002b91a54a7cc4510f099c4bfd6279502ec70164016250eebd1"
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             "index": "pypi",
-            "version": "==1.1.0"
+            "version": "==1.1.3"
         },
         "flake8-bugbear": {
             "hashes": [
@@ -701,11 +684,11 @@
         },
         "flake8-docstrings": {
             "hashes": [
-                "sha256:1666dd069c9c457ee57e80af3c1a6b37b00cc1801c6fde88e455131bb2e186cd",
-                "sha256:9c0db5a79a1affd70fdf53b8765c8a26bf968e59e0252d7f2fc546b41c0cda06"
+                "sha256:3d5a31c7ec6b7367ea6506a87ec293b94a0a46c0bce2bb4975b7f1d09b6f3717",
+                "sha256:a256ba91bc52307bef1de59e2a009c3cf61c3d0952dbe035d6ff7208940c2edc"
             ],
             "index": "pypi",
-            "version": "==1.4.0"
+            "version": "==1.5.0"
         },
         "flake8-import-order": {
             "hashes": [
@@ -740,10 +723,10 @@
         },
         "identify": {
             "hashes": [
-                "sha256:4f1fe9a59df4e80fcb0213086fcf502bc1765a01ea4fe8be48da3b65afd2a017",
-                "sha256:d8919589bd2a5f99c66302fec0ef9027b12ae150b0b0213999ad3f695fc7296e"
+                "sha256:1222b648251bdcb8deb240b294f450fbf704c7984e08baa92507e4ea10b436d5",
+                "sha256:d824ebe21f38325c771c41b08a95a761db1982f1fc0eee37c6c97df3f1636b96"
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-            "version": "==1.4.7"
+            "version": "==1.4.11"
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         "idna": {
             "hashes": [
@@ -754,11 +737,11 @@
         },
         "importlib-metadata": {
             "hashes": [
-                "sha256:aa18d7378b00b40847790e7c27e11673d7fed219354109d0e7b9e5b25dc3ad26",
-                "sha256:d5f18a79777f3aa179c145737780282e27b508fc8fd688cb17c7a813e8bd39af"
+                "sha256:06f5b3a99029c7134207dd882428a66992a9de2bef7c2b699b5641f9886c3302",
+                "sha256:b97607a1a18a5100839aec1dc26a1ea17ee0d93b20b0f008d80a5a050afb200b"
             ],
             "markers": "python_version < '3.8'",
-            "version": "==0.23"
+            "version": "==1.5.0"
         },
         "mccabe": {
             "hashes": [
@@ -767,48 +750,26 @@
             ],
             "version": "==0.6.1"
         },
-        "more-itertools": {
-            "hashes": [
-                "sha256:409cd48d4db7052af495b09dec721011634af3753ae1ef92d2b32f73a745f832",
-                "sha256:92b8c4b06dac4f0611c0729b2f2ede52b2e1bac1ab48f089c7ddc12e26bb60c4"
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-            "index": "pypi",
-            "version": "==7.2.0"
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             "hashes": [
-                "sha256:ad8259494cf1c9034539f6cced78a1da4840a4b157e23640bc4a0c0546b0cb7a"
+                "sha256:5b2438f2e42af54ca968dd1b374d14a1194848955187b0e5e4be1f73813a5212"
             ],
-            "version": "==1.3.3"
+            "version": "==1.3.5"
         },
         "packaging": {
             "hashes": [
-                "sha256:28b924174df7a2fa32c1953825ff29c61e2f5e082343165438812f00d3a7fc47",
-                "sha256:d9551545c6d761f3def1677baf08ab2a3ca17c56879e70fecba2fc4dde4ed108"
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-            "version": "==19.2"
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-                "sha256:fa5fa1622fa6dd5c030e9cad086fa19ef6a0cf6d7a2d12318e10cb49d6d68f34"
+                "sha256:170748228214b70b672c581a3dd610ee51f733018650740e98c7df862a583f73",
+                "sha256:e665345f9eef0c621aa0bf2f8d78cf6d21904eef16a93f020240b704a57f1334"
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-            "version": "==0.13.0"
+            "version": "==20.1"
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         "pre-commit": {
             "hashes": [
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-                "sha256:fa78ff96e8e9ac94c748388597693f18b041a181c94a4f039ad20f45287ba44a"
+                "sha256:8f48d8637bdae6fa70cc97db9c1dd5aa7c5c8bf71968932a380628c25978b850",
+                "sha256:f92a359477f3252452ae2e8d3029de77aec59415c16ae4189bcfba40b757e029"
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-            ],
-            "version": "==1.8.0"
+            "version": "==1.21.0"
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         "pycodestyle": {
             "hashes": [
@@ -819,10 +780,10 @@
         },
         "pydocstyle": {
             "hashes": [
-                "sha256:04c84e034ebb56eb6396c820442b8c4499ac5eb94a3bda88951ac3dc519b6058",
-                "sha256:66aff87ffe34b1e49bff2dd03a88ce6843be2f3346b0c9814410d34987fbab59"
+                "sha256:da7831660b7355307b32778c4a0dbfb137d89254ef31a2b2978f50fc0b4d7586",
+                "sha256:f4f5d210610c2d153fae39093d44224c17429e2ad7da12a8b419aba5c2f614b5"
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-            "version": "==4.0.1"
+            "version": "==5.0.2"
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         "pyflakes": {
             "hashes": [
@@ -833,45 +794,27 @@
         },
         "pyparsing": {
             "hashes": [
-                "sha256:6f98a7b9397e206d78cc01df10131398f1c8b8510a2f4d97d9abd82e1aacdd80",
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-                "sha256:cc6620b96bc667a0c8d4fa592a8c9c94178a1bd6cc799dbb057dfd9286d31a31"
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-            "version": "==5.1.3"
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-        "pytest-cov": {
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-                "sha256:e00ea4fdde970725482f1f35630d12f074e121a23801aabf2ae154ec6bdd343a"
+                "sha256:4c830582a84fb022400b85429791bc551f1f4871c33f23e44f353119e92f969f",
+                "sha256:c342dccb5250c08d45fd6f8b4a559613ca603b57498511740e65cd11a2e7dcec"
             ],
-            "index": "pypi",
-            "version": "==2.7.1"
+            "version": "==2.4.6"
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         "pyyaml": {
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-                "sha256:f81025eddd0327c7d4cfe9b62cf33190e1e736cc6e97502b3ec425f574b3e7a8"
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+                "sha256:1cf708e2ac57f3aabc87405f04b86354f66799c8e62c28c5fc5f88b5521b2dbf",
+                "sha256:24521fa2890642614558b492b473bee0ac1f8057a7263156b02e8b14c88ce6f5",
+                "sha256:4fee71aa5bc6ed9d5f116327c04273e25ae31a3020386916905767ec4fc5317e",
+                "sha256:70024e02197337533eef7b85b068212420f950319cc8c580261963aefc75f811",
+                "sha256:74782fbd4d4f87ff04159e986886931456a1894c61229be9eaf4de6f6e44b99e",
+                "sha256:940532b111b1952befd7db542c370887a8611660d2b9becff75d39355303d82d",
+                "sha256:cb1f2f5e426dc9f07a7681419fe39cee823bb74f723f36f70399123f439e9b20",
+                "sha256:dbbb2379c19ed6042e8f11f2a2c66d39cceb8aeace421bfc29d085d93eda3689",
+                "sha256:e3a057b7a64f1222b56e47bcff5e4b94c4f61faac04c7c4ecb1985e18caa3994",
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-            "version": "==5.1.2"
+            "version": "==5.3"
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         "requests": {
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@@ -891,16 +834,17 @@
         },
         "six": {
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-                "sha256:3350809f0555b11f552448330d0b52d5f24c91a322ea4a15ef22629740f3761c",
-                "sha256:d16a0141ec1a18405cd4ce8b4613101da75da0e9a7aec5bdd4fa804d0e0eba73"
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-            "version": "==1.12.0"
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         "snowballstemmer": {
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-                "sha256:713e53b79cbcf97bc5245a06080a33d54a77e7cce2f789c835a143bcdb5c033e"
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-            "version": "==1.9.1"
+            "version": "==2.0.0"
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         "toml": {
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@@ -911,23 +855,38 @@
         },
         "typed-ast": {
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+            ],
+            "markers": "python_version < '3.8'",
+            "version": "==1.4.1"
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+        "unittest-xml-reporting": {
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+            "version": "==2.5.2"
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         "urllib3": {
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@@ -939,24 +898,17 @@
         },
         "virtualenv": {
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-            "version": "==0.1.7"
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-                "sha256:f06903e9f1f43b12d371004b4ac7b06ab39a44adc747266928ae6debfa7b3335"
+                "sha256:ccc94ed0909b58ffe34430ea5451f07bc0c76467d7081619a454bf5c98b89e28",
+                "sha256:feae2f18633c32fc71f2de629bfb3bd3c9325cd4419642b1f1da42ee488d9b98"
             ],
-            "version": "==0.6.0"
+            "version": "==2.1.0"
         }
     }
 }
diff --git a/README.md b/README.md
index 7a7f1b992..1e7b21271 100644
--- a/README.md
+++ b/README.md
@@ -1,6 +1,6 @@
 # Python Utility Bot
 
-[![Discord](https://img.shields.io/discord/267624335836053506?color=%237289DA&label=Python%20Discord&logo=discord&logoColor=white)](https://discord.gg/2B963hn)
+[![Discord](https://img.shields.io/static/v1?label=Python%20Discord&logo=discord&message=%3E30k%20members&color=%237289DA&logoColor=white)](https://discord.gg/2B963hn)
 [![Build Status](https://dev.azure.com/python-discord/Python%20Discord/_apis/build/status/Bot?branchName=master)](https://dev.azure.com/python-discord/Python%20Discord/_build/latest?definitionId=1&branchName=master)
 [![Tests](https://img.shields.io/azure-devops/tests/python-discord/Python%20Discord/1?compact_message)](https://dev.azure.com/python-discord/Python%20Discord/_apis/build/status/Bot?branchName=master)
 [![Coverage](https://img.shields.io/azure-devops/coverage/python-discord/Python%20Discord/1/master)](https://dev.azure.com/python-discord/Python%20Discord/_apis/build/status/Bot?branchName=master)
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index c22bac089..0400ac4d2 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -30,9 +30,12 @@ jobs:
       - script: python -m flake8
         displayName: 'Run linter'
 
-      - script: BOT_API_KEY=foo BOT_TOKEN=bar WOLFRAM_API_KEY=baz python -m pytest --junitxml=junit.xml --cov=bot --cov-branch --cov-report=term --cov-report=xml tests
+      - script: BOT_API_KEY=foo BOT_TOKEN=bar WOLFRAM_API_KEY=baz REDDIT_CLIENT_ID=spam REDDIT_SECRET=ham coverage run -m xmlrunner
         displayName: Run tests
 
+      - script: coverage report -m && coverage xml -o coverage.xml
+        displayName: Generate test coverage report
+
       - task: PublishCodeCoverageResults@1
         displayName: 'Publish Coverage Results'
         condition: succeededOrFailed()
@@ -41,11 +44,11 @@ jobs:
           summaryFileLocation: coverage.xml
 
       - task: PublishTestResults@2
-        displayName: 'Publish Test Results'
         condition: succeededOrFailed()
+        displayName: 'Publish Test Results'
         inputs:
-          testResultsFiles: junit.xml
-          testRunTitle: 'Bot Test results'
+          testResultsFiles: '**/TEST-*.xml'
+          testRunTitle: 'Bot Test Results'
 
   - job: build
     displayName: 'Build & Push Container'
diff --git a/bot/__init__.py b/bot/__init__.py
index 4a2df730d..789ace5c0 100644
--- a/bot/__init__.py
+++ b/bot/__init__.py
@@ -6,6 +6,7 @@ from pathlib import Path
 
 from logmatic import JsonFormatter
 
+
 logging.TRACE = 5
 logging.addLevelName(logging.TRACE, "TRACE")
 
diff --git a/bot/__main__.py b/bot/__main__.py
index 19a7e5ec6..84bc7094b 100644
--- a/bot/__main__.py
+++ b/bot/__main__.py
@@ -1,18 +1,11 @@
-import asyncio
-import logging
-import socket
-
 import discord
-from aiohttp import AsyncResolver, ClientSession, TCPConnector
-from discord.ext.commands import Bot, when_mentioned_or
+from discord.ext.commands import when_mentioned_or
 
 from bot import patches
-from bot.api import APIClient, APILoggingHandler
+from bot.bot import Bot
 from bot.constants import Bot as BotConfig, DEBUG_MODE
 
 
-log = logging.getLogger('bot')
-
 bot = Bot(
     command_prefix=when_mentioned_or(BotConfig.prefix),
     activity=discord.Game(name="Commands: !help"),
@@ -20,18 +13,6 @@ bot = Bot(
     max_messages=10_000,
 )
 
-# Global aiohttp session for all cogs
-# - Uses asyncio for DNS resolution instead of threads, so we don't spam threads
-# - Uses AF_INET as its socket family to prevent https related problems both locally and in prod.
-bot.http_session = ClientSession(
-    connector=TCPConnector(
-        resolver=AsyncResolver(),
-        family=socket.AF_INET,
-    )
-)
-bot.api_client = APIClient(loop=asyncio.get_event_loop())
-log.addHandler(APILoggingHandler(bot.api_client))
-
 # Internal/debug
 bot.load_extension("bot.cogs.error_handler")
 bot.load_extension("bot.cogs.filtering")
@@ -39,6 +20,7 @@ bot.load_extension("bot.cogs.logging")
 bot.load_extension("bot.cogs.security")
 
 # Commands, etc
+bot.load_extension("bot.cogs.antimalware")
 bot.load_extension("bot.cogs.antispam")
 bot.load_extension("bot.cogs.bot")
 bot.load_extension("bot.cogs.clean")
@@ -54,6 +36,7 @@ if not DEBUG_MODE:
 bot.load_extension("bot.cogs.alias")
 bot.load_extension("bot.cogs.defcon")
 bot.load_extension("bot.cogs.eval")
+bot.load_extension("bot.cogs.duck_pond")
 bot.load_extension("bot.cogs.free")
 bot.load_extension("bot.cogs.information")
 bot.load_extension("bot.cogs.jams")
@@ -75,6 +58,3 @@ if not hasattr(discord.message.Message, '_handle_edited_timestamp'):
     patches.message_edited_at.apply_patch()
 
 bot.run(BotConfig.token)
-
-# This calls a coroutine, so it doesn't do anything at the moment.
-# bot.http_session.close()  # Close the aiohttp session when the bot finishes running
diff --git a/bot/api.py b/bot/api.py
index 7f26e5305..56db99828 100644
--- a/bot/api.py
+++ b/bot/api.py
@@ -32,7 +32,7 @@ class ResponseCodeError(ValueError):
 class APIClient:
     """Django Site API wrapper."""
 
-    def __init__(self, **kwargs):
+    def __init__(self, loop: asyncio.AbstractEventLoop, **kwargs):
         auth_headers = {
             'Authorization': f"Token {Keys.site_api}"
         }
@@ -42,12 +42,39 @@ class APIClient:
         else:
             kwargs['headers'] = auth_headers
 
-        self.session = aiohttp.ClientSession(**kwargs)
+        self.session: Optional[aiohttp.ClientSession] = None
+        self.loop = loop
+
+        self._ready = asyncio.Event(loop=loop)
+        self._creation_task = None
+        self._session_args = kwargs
+
+        self.recreate()
 
     @staticmethod
     def _url_for(endpoint: str) -> str:
         return f"{URLs.site_schema}{URLs.site_api}/{quote_url(endpoint)}"
 
+    async def _create_session(self) -> None:
+        """Create the aiohttp session and set the ready event."""
+        self.session = aiohttp.ClientSession(**self._session_args)
+        self._ready.set()
+
+    async def close(self) -> None:
+        """Close the aiohttp session and unset the ready event."""
+        if not self._ready.is_set():
+            return
+
+        await self.session.close()
+        self._ready.clear()
+
+    def recreate(self) -> None:
+        """Schedule the aiohttp session to be created if it's been closed."""
+        if self.session is None or self.session.closed:
+            # Don't schedule a task if one is already in progress.
+            if self._creation_task is None or self._creation_task.done():
+                self._creation_task = self.loop.create_task(self._create_session())
+
     async def maybe_raise_for_status(self, response: aiohttp.ClientResponse, should_raise: bool) -> None:
         """Raise ResponseCodeError for non-OK response if an exception should be raised."""
         if should_raise and response.status >= 400:
@@ -60,30 +87,40 @@ class APIClient:
 
     async def get(self, endpoint: str, *args, raise_for_status: bool = True, **kwargs) -> dict:
         """Site API GET."""
+        await self._ready.wait()
+
         async with self.session.get(self._url_for(endpoint), *args, **kwargs) as resp:
             await self.maybe_raise_for_status(resp, raise_for_status)
             return await resp.json()
 
     async def patch(self, endpoint: str, *args, raise_for_status: bool = True, **kwargs) -> dict:
         """Site API PATCH."""
+        await self._ready.wait()
+
         async with self.session.patch(self._url_for(endpoint), *args, **kwargs) as resp:
             await self.maybe_raise_for_status(resp, raise_for_status)
             return await resp.json()
 
     async def post(self, endpoint: str, *args, raise_for_status: bool = True, **kwargs) -> dict:
         """Site API POST."""
+        await self._ready.wait()
+
         async with self.session.post(self._url_for(endpoint), *args, **kwargs) as resp:
             await self.maybe_raise_for_status(resp, raise_for_status)
             return await resp.json()
 
     async def put(self, endpoint: str, *args, raise_for_status: bool = True, **kwargs) -> dict:
         """Site API PUT."""
+        await self._ready.wait()
+
         async with self.session.put(self._url_for(endpoint), *args, **kwargs) as resp:
             await self.maybe_raise_for_status(resp, raise_for_status)
             return await resp.json()
 
     async def delete(self, endpoint: str, *args, raise_for_status: bool = True, **kwargs) -> Optional[dict]:
         """Site API DELETE."""
+        await self._ready.wait()
+
         async with self.session.delete(self._url_for(endpoint), *args, **kwargs) as resp:
             if resp.status == 204:
                 return None
diff --git a/bot/bot.py b/bot/bot.py
new file mode 100644
index 000000000..8f808272f
--- /dev/null
+++ b/bot/bot.py
@@ -0,0 +1,53 @@
+import logging
+import socket
+from typing import Optional
+
+import aiohttp
+from discord.ext import commands
+
+from bot import api
+
+log = logging.getLogger('bot')
+
+
+class Bot(commands.Bot):
+    """A subclass of `discord.ext.commands.Bot` with an aiohttp session and an API client."""
+
+    def __init__(self, *args, **kwargs):
+        # Use asyncio for DNS resolution instead of threads so threads aren't spammed.
+        # Use AF_INET as its socket family to prevent HTTPS related problems both locally
+        # and in production.
+        self.connector = aiohttp.TCPConnector(
+            resolver=aiohttp.AsyncResolver(),
+            family=socket.AF_INET,
+        )
+
+        super().__init__(*args, connector=self.connector, **kwargs)
+
+        self.http_session: Optional[aiohttp.ClientSession] = None
+        self.api_client = api.APIClient(loop=self.loop, connector=self.connector)
+
+        log.addHandler(api.APILoggingHandler(self.api_client))
+
+    def add_cog(self, cog: commands.Cog) -> None:
+        """Adds a "cog" to the bot and logs the operation."""
+        super().add_cog(cog)
+        log.info(f"Cog loaded: {cog.qualified_name}")
+
+    def clear(self) -> None:
+        """Clears the internal state of the bot and resets the API client."""
+        super().clear()
+        self.api_client.recreate()
+
+    async def close(self) -> None:
+        """Close the aiohttp session after closing the Discord connection."""
+        await super().close()
+
+        await self.http_session.close()
+        await self.api_client.close()
+
+    async def start(self, *args, **kwargs) -> None:
+        """Open an aiohttp session before logging in and connecting to Discord."""
+        self.http_session = aiohttp.ClientSession(connector=self.connector)
+
+        await super().start(*args, **kwargs)
diff --git a/bot/cogs/alias.py b/bot/cogs/alias.py
index 6648805e9..0b800575f 100644
--- a/bot/cogs/alias.py
+++ b/bot/cogs/alias.py
@@ -1,13 +1,15 @@
 import inspect
 import logging
-from typing import Union
 
-from discord import Colour, Embed, Member, User
-from discord.ext.commands import Bot, Cog, Command, Context, clean_content, command, group
+from discord import Colour, Embed
+from discord.ext.commands import (
+    Cog, Command, Context, Greedy,
+    clean_content, command, group,
+)
 
+from bot.bot import Bot
 from bot.cogs.extensions import Extension
-from bot.cogs.watchchannels.watchchannel import proxy_user
-from bot.converters import TagNameConverter
+from bot.converters import FetchedMember, TagNameConverter
 from bot.pagination import LinePaginator
 
 log = logging.getLogger(__name__)
@@ -60,12 +62,12 @@ class Alias (Cog):
         await self.invoke(ctx, "site tools")
 
     @command(name="watch", hidden=True)
-    async def bigbrother_watch_alias(self, ctx: Context, user: Union[Member, User, proxy_user], *, reason: str) -> None:
+    async def bigbrother_watch_alias(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """Alias for invoking <prefix>bigbrother watch [user] [reason]."""
         await self.invoke(ctx, "bigbrother watch", user, reason=reason)
 
     @command(name="unwatch", hidden=True)
-    async def bigbrother_unwatch_alias(self, ctx: Context, user: Union[User, proxy_user], *, reason: str) -> None:
+    async def bigbrother_unwatch_alias(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """Alias for invoking <prefix>bigbrother unwatch [user] [reason]."""
         await self.invoke(ctx, "bigbrother unwatch", user, reason=reason)
 
@@ -79,10 +81,10 @@ class Alias (Cog):
         """Alias for invoking <prefix>site faq."""
         await self.invoke(ctx, "site faq")
 
-    @command(name="rules", hidden=True)
-    async def site_rules_alias(self, ctx: Context) -> None:
+    @command(name="rules", aliases=("rule",), hidden=True)
+    async def site_rules_alias(self, ctx: Context, rules: Greedy[int], *_: str) -> None:
         """Alias for invoking <prefix>site rules."""
-        await self.invoke(ctx, "site rules")
+        await self.invoke(ctx, "site rules", *rules)
 
     @command(name="reload", hidden=True)
     async def extensions_reload_alias(self, ctx: Context, *extensions: Extension) -> None:
@@ -131,12 +133,12 @@ class Alias (Cog):
         await self.invoke(ctx, "docs get", symbol)
 
     @command(name="nominate", hidden=True)
-    async def nomination_add_alias(self, ctx: Context, user: Union[Member, User, proxy_user], *, reason: str) -> None:
+    async def nomination_add_alias(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """Alias for invoking <prefix>talentpool add [user] [reason]."""
         await self.invoke(ctx, "talentpool add", user, reason=reason)
 
     @command(name="unnominate", hidden=True)
-    async def nomination_end_alias(self, ctx: Context, user: Union[User, proxy_user], *, reason: str) -> None:
+    async def nomination_end_alias(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """Alias for invoking <prefix>nomination end [user] [reason]."""
         await self.invoke(ctx, "nomination end", user, reason=reason)
 
@@ -147,6 +149,5 @@ class Alias (Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Alias cog load."""
+    """Load the Alias cog."""
     bot.add_cog(Alias(bot))
-    log.info("Cog loaded: Alias")
diff --git a/bot/cogs/antimalware.py b/bot/cogs/antimalware.py
new file mode 100644
index 000000000..28e3e5d96
--- /dev/null
+++ b/bot/cogs/antimalware.py
@@ -0,0 +1,54 @@
+import logging
+
+from discord import Embed, Message, NotFound
+from discord.ext.commands import Cog
+
+from bot.bot import Bot
+from bot.constants import AntiMalware as AntiMalwareConfig, Channels, URLs
+
+log = logging.getLogger(__name__)
+
+
+class AntiMalware(Cog):
+    """Delete messages which contain attachments with non-whitelisted file extensions."""
+
+    def __init__(self, bot: Bot):
+        self.bot = bot
+
+    @Cog.listener()
+    async def on_message(self, message: Message) -> None:
+        """Identify messages with prohibited attachments."""
+        if not message.attachments:
+            return
+
+        embed = Embed()
+        for attachment in message.attachments:
+            filename = attachment.filename.lower()
+            if filename.endswith('.py'):
+                embed.description = (
+                    f"It looks like you tried to attach a Python file - please "
+                    f"use a code-pasting service such as {URLs.site_schema}{URLs.site_paste}"
+                )
+                break  # Other detections irrelevant because we prioritize the .py message.
+            if not filename.endswith(tuple(AntiMalwareConfig.whitelist)):
+                whitelisted_types = ', '.join(AntiMalwareConfig.whitelist)
+                meta_channel = self.bot.get_channel(Channels.meta)
+                embed.description = (
+                    f"It looks like you tried to attach a file type that we "
+                    f"do not allow. We currently allow the following file "
+                    f"types: **{whitelisted_types}**. \n\n Feel free to ask "
+                    f"in {meta_channel.mention} if you think this is a mistake."
+                )
+        if embed.description:
+            await message.channel.send(f"Hey {message.author.mention}!", embed=embed)
+
+            # Delete the offending message:
+            try:
+                await message.delete()
+            except NotFound:
+                log.info(f"Tried to delete message `{message.id}`, but message could not be found.")
+
+
+def setup(bot: Bot) -> None:
+    """Load the AntiMalware cog."""
+    bot.add_cog(AntiMalware(bot))
diff --git a/bot/cogs/antispam.py b/bot/cogs/antispam.py
index 1b394048a..f67ef6f05 100644
--- a/bot/cogs/antispam.py
+++ b/bot/cogs/antispam.py
@@ -7,9 +7,10 @@ from operator import itemgetter
 from typing import Dict, Iterable, List, Set
 
 from discord import Colour, Member, Message, NotFound, Object, TextChannel
-from discord.ext.commands import Bot, Cog
+from discord.ext.commands import Cog
 
 from bot import rules
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
 from bot.constants import (
     AntiSpam as AntiSpamConfig, Channels,
@@ -18,6 +19,7 @@ from bot.constants import (
     STAFF_ROLES,
 )
 from bot.converters import Duration
+from bot.utils.messages import send_attachments
 
 
 log = logging.getLogger(__name__)
@@ -44,8 +46,9 @@ class DeletionContext:
     members: Dict[int, Member] = field(default_factory=dict)
     rules: Set[str] = field(default_factory=set)
     messages: Dict[int, Message] = field(default_factory=dict)
+    attachments: List[List[str]] = field(default_factory=list)
 
-    def add(self, rule_name: str, members: Iterable[Member], messages: Iterable[Message]) -> None:
+    async def add(self, rule_name: str, members: Iterable[Member], messages: Iterable[Message]) -> None:
         """Adds new rule violation events to the deletion context."""
         self.rules.add(rule_name)
 
@@ -57,9 +60,14 @@ class DeletionContext:
             if message.id not in self.messages:
                 self.messages[message.id] = message
 
+                # Re-upload attachments
+                destination = message.guild.get_channel(Channels.attachment_log)
+                urls = await send_attachments(message, destination, link_large=False)
+                self.attachments.append(urls)
+
     async def upload_messages(self, actor_id: int, modlog: ModLog) -> None:
         """Method that takes care of uploading the queue and posting modlog alert."""
-        triggered_by_users = ", ".join(f"{m.display_name}#{m.discriminator} (`{m.id}`)" for m in self.members.values())
+        triggered_by_users = ", ".join(f"{m} (`{m.id}`)" for m in self.members.values())
 
         mod_alert_message = (
             f"**Triggered by:** {triggered_by_users}\n"
@@ -69,7 +77,7 @@ class DeletionContext:
 
         # For multiple messages or those with excessive newlines, use the logs API
         if len(self.messages) > 1 or 'newlines' in self.rules:
-            url = await modlog.upload_log(self.messages.values(), actor_id)
+            url = await modlog.upload_log(self.messages.values(), actor_id, self.attachments)
             mod_alert_message += f"A complete log of the offending messages can be found [here]({url})"
         else:
             mod_alert_message += "Message:\n"
@@ -97,7 +105,7 @@ class DeletionContext:
 class AntiSpam(Cog):
     """Cog that controls our anti-spam measures."""
 
-    def __init__(self, bot: Bot, validation_errors: bool) -> None:
+    def __init__(self, bot: Bot, validation_errors: Dict[str, str]) -> None:
         self.bot = bot
         self.validation_errors = validation_errors
         role_id = AntiSpamConfig.punishment['role_id']
@@ -105,7 +113,6 @@ class AntiSpam(Cog):
         self.expiration_date_converter = Duration()
 
         self.message_deletion_queue = dict()
-        self.queue_consumption_tasks = dict()
 
         self.bot.loop.create_task(self.alert_on_validation_error())
 
@@ -179,15 +186,14 @@ class AntiSpam(Cog):
                 full_reason = f"`{rule_name}` rule: {reason}"
 
                 # If there's no spam event going on for this channel, start a new Message Deletion Context
-                if message.channel.id not in self.message_deletion_queue:
-                    log.trace(f"Creating queue for channel `{message.channel.id}`")
-                    self.message_deletion_queue[message.channel.id] = DeletionContext(channel=message.channel)
-                    self.queue_consumption_tasks = self.bot.loop.create_task(
-                        self._process_deletion_context(message.channel.id)
-                    )
+                channel = message.channel
+                if channel.id not in self.message_deletion_queue:
+                    log.trace(f"Creating queue for channel `{channel.id}`")
+                    self.message_deletion_queue[message.channel.id] = DeletionContext(channel)
+                    self.bot.loop.create_task(self._process_deletion_context(message.channel.id))
 
                 # Add the relevant of this trigger to the Deletion Context
-                self.message_deletion_queue[message.channel.id].add(
+                await self.message_deletion_queue[message.channel.id].add(
                     rule_name=rule_name,
                     members=members,
                     messages=relevant_messages
@@ -201,7 +207,7 @@ class AntiSpam(Cog):
                         self.punish(message, member, full_reason)
                     )
 
-                await self.maybe_delete_messages(message.channel, relevant_messages)
+                await self.maybe_delete_messages(channel, relevant_messages)
                 break
 
     async def punish(self, msg: Message, member: Member, reason: str) -> None:
@@ -254,10 +260,10 @@ class AntiSpam(Cog):
         await deletion_context.upload_messages(self.bot.user.id, self.mod_log)
 
 
-def validate_config(rules: Mapping = AntiSpamConfig.rules) -> Dict[str, str]:
+def validate_config(rules_: Mapping = AntiSpamConfig.rules) -> Dict[str, str]:
     """Validates the antispam configs."""
     validation_errors = {}
-    for name, config in rules.items():
+    for name, config in rules_.items():
         if name not in RULE_FUNCTION_MAPPING:
             log.error(
                 f"Unrecognized antispam rule `{name}`. "
@@ -276,7 +282,6 @@ def validate_config(rules: Mapping = AntiSpamConfig.rules) -> Dict[str, str]:
 
 
 def setup(bot: Bot) -> None:
-    """Antispam cog load."""
+    """Validate the AntiSpam configs and load the AntiSpam cog."""
     validation_errors = validate_config()
     bot.add_cog(AntiSpam(bot, validation_errors))
-    log.info("Cog loaded: AntiSpam")
diff --git a/bot/cogs/bot.py b/bot/cogs/bot.py
index 7583b2f2d..73b1e8f41 100644
--- a/bot/cogs/bot.py
+++ b/bot/cogs/bot.py
@@ -4,9 +4,11 @@ import re
 import time
 from typing import Optional, Tuple
 
-from discord import Embed, Message, RawMessageUpdateEvent
-from discord.ext.commands import Bot, Cog, Context, command, group
+from discord import Embed, Message, RawMessageUpdateEvent, TextChannel
+from discord.ext.commands import Cog, Context, command, group
 
+from bot.bot import Bot
+from bot.cogs.token_remover import TokenRemover
 from bot.constants import Channels, DEBUG_MODE, Guild, MODERATION_ROLES, Roles, URLs
 from bot.decorators import with_role
 from bot.utils.messages import wait_for_deletion
@@ -16,7 +18,7 @@ log = logging.getLogger(__name__)
 RE_MARKDOWN = re.compile(r'([*_~`|>])')
 
 
-class Bot(Cog):
+class BotCog(Cog, name="Bot"):
     """Bot information commands."""
 
     def __init__(self, bot: Bot):
@@ -71,9 +73,12 @@ class Bot(Cog):
 
     @command(name='echo', aliases=('print',))
     @with_role(*MODERATION_ROLES)
-    async def echo_command(self, ctx: Context, *, text: str) -> None:
-        """Send the input verbatim to the current channel."""
-        await ctx.send(text)
+    async def echo_command(self, ctx: Context, channel: Optional[TextChannel], *, text: str) -> None:
+        """Repeat the given message in either a specified channel or the current channel."""
+        if channel is None:
+            await ctx.send(text)
+        else:
+            await channel.send(text)
 
     @command(name='embed')
     @with_role(*MODERATION_ROLES)
@@ -235,9 +240,10 @@ class Bot(Cog):
             )
             and not msg.author.bot
             and len(msg.content.splitlines()) > 3
+            and not TokenRemover.is_token_in_message(msg)
         )
 
-        if parse_codeblock:
+        if parse_codeblock:  # no token in the msg
             on_cooldown = (time.time() - self.channel_cooldowns.get(msg.channel.id, 0)) < 300
             if not on_cooldown or DEBUG_MODE:
                 try:
@@ -370,10 +376,9 @@ class Bot(Cog):
             bot_message = await channel.fetch_message(self.codeblock_message_ids[payload.message_id])
             await bot_message.delete()
             del self.codeblock_message_ids[payload.message_id]
-            log.trace("User's incorrect code block has been fixed.  Removing bot formatting message.")
+            log.trace("User's incorrect code block has been fixed. Removing bot formatting message.")
 
 
 def setup(bot: Bot) -> None:
-    """Bot cog load."""
-    bot.add_cog(Bot(bot))
-    log.info("Cog loaded: Bot")
+    """Load the Bot cog."""
+    bot.add_cog(BotCog(bot))
diff --git a/bot/cogs/clean.py b/bot/cogs/clean.py
index dca411d01..2104efe57 100644
--- a/bot/cogs/clean.py
+++ b/bot/cogs/clean.py
@@ -3,9 +3,10 @@ import random
 import re
 from typing import Optional
 
-from discord import Colour, Embed, Message, User
-from discord.ext.commands import Bot, Cog, Context, group
+from discord import Colour, Embed, Message, TextChannel, User
+from discord.ext.commands import Cog, Context, group
 
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
 from bot.constants import (
     Channels, CleanMessages, Colours, Event,
@@ -37,9 +38,13 @@ class Clean(Cog):
         return self.bot.get_cog("ModLog")
 
     async def _clean_messages(
-            self, amount: int, ctx: Context,
-            bots_only: bool = False, user: User = None,
-            regex: Optional[str] = None
+        self,
+        amount: int,
+        ctx: Context,
+        bots_only: bool = False,
+        user: User = None,
+        regex: Optional[str] = None,
+        channel: Optional[TextChannel] = None
     ) -> None:
         """A helper function that does the actual message cleaning."""
         def predicate_bots_only(message: Message) -> bool:
@@ -104,6 +109,10 @@ class Clean(Cog):
         else:
             predicate = None                     # Delete all messages
 
+        # Default to using the invoking context's channel
+        if not channel:
+            channel = ctx.channel
+
         # Look through the history and retrieve message data
         messages = []
         message_ids = []
@@ -111,7 +120,7 @@ class Clean(Cog):
         invocation_deleted = False
 
         # To account for the invocation message, we index `amount + 1` messages.
-        async for message in ctx.channel.history(limit=amount + 1):
+        async for message in channel.history(limit=amount + 1):
 
             # If at any point the cancel command is invoked, we should stop.
             if not self.cleaning:
@@ -135,7 +144,7 @@ class Clean(Cog):
         self.mod_log.ignore(Event.message_delete, *message_ids)
 
         # Use bulk delete to actually do the cleaning. It's far faster.
-        await ctx.channel.purge(
+        await channel.purge(
             limit=amount,
             check=predicate
         )
@@ -155,7 +164,7 @@ class Clean(Cog):
 
         # Build the embed and send it
         message = (
-            f"**{len(message_ids)}** messages deleted in <#{ctx.channel.id}> by **{ctx.author.name}**\n\n"
+            f"**{len(message_ids)}** messages deleted in <#{channel.id}> by **{ctx.author.name}**\n\n"
             f"A log of the deleted messages can be found [here]({log_url})."
         )
 
@@ -167,7 +176,7 @@ class Clean(Cog):
             channel_id=Channels.modlog,
         )
 
-    @group(invoke_without_command=True, name="clean", hidden=True)
+    @group(invoke_without_command=True, name="clean", aliases=["purge"])
     @with_role(*MODERATION_ROLES)
     async def clean_group(self, ctx: Context) -> None:
         """Commands for cleaning messages in channels."""
@@ -175,27 +184,49 @@ class Clean(Cog):
 
     @clean_group.command(name="user", aliases=["users"])
     @with_role(*MODERATION_ROLES)
-    async def clean_user(self, ctx: Context, user: User, amount: int = 10) -> None:
+    async def clean_user(
+        self,
+        ctx: Context,
+        user: User,
+        amount: Optional[int] = 10,
+        channel: TextChannel = None
+    ) -> None:
         """Delete messages posted by the provided user, stop cleaning after traversing `amount` messages."""
-        await self._clean_messages(amount, ctx, user=user)
+        await self._clean_messages(amount, ctx, user=user, channel=channel)
 
     @clean_group.command(name="all", aliases=["everything"])
     @with_role(*MODERATION_ROLES)
-    async def clean_all(self, ctx: Context, amount: int = 10) -> None:
+    async def clean_all(
+        self,
+        ctx: Context,
+        amount: Optional[int] = 10,
+        channel: TextChannel = None
+    ) -> None:
         """Delete all messages, regardless of poster, stop cleaning after traversing `amount` messages."""
-        await self._clean_messages(amount, ctx)
+        await self._clean_messages(amount, ctx, channel=channel)
 
     @clean_group.command(name="bots", aliases=["bot"])
     @with_role(*MODERATION_ROLES)
-    async def clean_bots(self, ctx: Context, amount: int = 10) -> None:
+    async def clean_bots(
+        self,
+        ctx: Context,
+        amount: Optional[int] = 10,
+        channel: TextChannel = None
+    ) -> None:
         """Delete all messages posted by a bot, stop cleaning after traversing `amount` messages."""
-        await self._clean_messages(amount, ctx, bots_only=True)
+        await self._clean_messages(amount, ctx, bots_only=True, channel=channel)
 
     @clean_group.command(name="regex", aliases=["word", "expression"])
     @with_role(*MODERATION_ROLES)
-    async def clean_regex(self, ctx: Context, regex: str, amount: int = 10) -> None:
+    async def clean_regex(
+        self,
+        ctx: Context,
+        regex: str,
+        amount: Optional[int] = 10,
+        channel: TextChannel = None
+    ) -> None:
         """Delete all messages that match a certain regex, stop cleaning after traversing `amount` messages."""
-        await self._clean_messages(amount, ctx, regex=regex)
+        await self._clean_messages(amount, ctx, regex=regex, channel=channel)
 
     @clean_group.command(name="stop", aliases=["cancel", "abort"])
     @with_role(*MODERATION_ROLES)
@@ -211,6 +242,5 @@ class Clean(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Clean cog load."""
+    """Load the Clean cog."""
     bot.add_cog(Clean(bot))
-    log.info("Cog loaded: Clean")
diff --git a/bot/cogs/defcon.py b/bot/cogs/defcon.py
index 70e101baa..3e7350fcc 100644
--- a/bot/cogs/defcon.py
+++ b/bot/cogs/defcon.py
@@ -1,9 +1,14 @@
+from __future__ import annotations
+
 import logging
+from collections import namedtuple
 from datetime import datetime, timedelta
+from enum import Enum
 
 from discord import Colour, Embed, Member
-from discord.ext.commands import Bot, Cog, Context, group
+from discord.ext.commands import Cog, Context, group
 
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
 from bot.constants import Channels, Colours, Emojis, Event, Icons, Roles
 from bot.decorators import with_role
@@ -24,6 +29,16 @@ will be resolved soon. In the meantime, please feel free to peruse the resources
 BASE_CHANNEL_TOPIC = "Python Discord Defense Mechanism"
 
 
+class Action(Enum):
+    """Defcon Action."""
+
+    ActionInfo = namedtuple('LogInfoDetails', ['icon', 'color', 'template'])
+
+    ENABLED = ActionInfo(Icons.defcon_enabled, Colours.soft_green, "**Days:** {days}\n\n")
+    DISABLED = ActionInfo(Icons.defcon_disabled, Colours.soft_red, "")
+    UPDATED = ActionInfo(Icons.defcon_updated, Colour.blurple(), "**Days:** {days}\n\n")
+
+
 class Defcon(Cog):
     """Time-sensitive server defense mechanisms."""
 
@@ -46,6 +61,7 @@ class Defcon(Cog):
         """On cog load, try to synchronize DEFCON settings to the API."""
         await self.bot.wait_until_ready()
         self.channel = await self.bot.fetch_channel(Channels.defcon)
+
         try:
             response = await self.bot.api_client.get('bot/bot-settings/defcon')
             data = response['data']
@@ -90,8 +106,7 @@ class Defcon(Cog):
                 await member.kick(reason="DEFCON active, user is too new")
 
                 message = (
-                    f"{member.name}#{member.discriminator} (`{member.id}`) "
-                    f"was denied entry because their account is too new."
+                    f"{member} (`{member.id}`) was denied entry because their account is too new."
                 )
 
                 if not message_sent:
@@ -108,39 +123,39 @@ class Defcon(Cog):
         """Check the DEFCON status or run a subcommand."""
         await ctx.invoke(self.bot.get_command("help"), "defcon")
 
-    @defcon_group.command(name='enable', aliases=('on', 'e'))
-    @with_role(Roles.admin, Roles.owner)
-    async def enable_command(self, ctx: Context) -> None:
-        """
-        Enable DEFCON mode. Useful in a pinch, but be sure you know what you're doing!
-
-        Currently, this just adds an account age requirement. Use !defcon days <int> to set how old an account must be,
-        in days.
-        """
-        self.enabled = True
-
+    async def _defcon_action(self, ctx: Context, days: int, action: Action) -> None:
+        """Providing a structured way to do an defcon action."""
+        error = None
         try:
             await self.bot.api_client.put(
                 'bot/bot-settings/defcon',
                 json={
                     'name': 'defcon',
                     'data': {
-                        'enabled': True,
                         # TODO: retrieve old days count
-                        'days': 0
+                        'days': days,
+                        'enabled': action is not Action.DISABLED,
                     }
                 }
             )
-
-        except Exception as e:
+        except Exception as err:
             log.exception("Unable to update DEFCON settings.")
-            await ctx.send(self.build_defcon_msg("enabled", e))
-            await self.send_defcon_log("enabled", ctx.author, e)
+            error = err
+        finally:
+            await ctx.send(self.build_defcon_msg(action, error))
+            await self.send_defcon_log(action, ctx.author, error)
 
-        else:
-            await ctx.send(self.build_defcon_msg("enabled"))
-            await self.send_defcon_log("enabled", ctx.author)
+    @defcon_group.command(name='enable', aliases=('on', 'e'))
+    @with_role(Roles.admin, Roles.owner)
+    async def enable_command(self, ctx: Context) -> None:
+        """
+        Enable DEFCON mode. Useful in a pinch, but be sure you know what you're doing!
 
+        Currently, this just adds an account age requirement. Use !defcon days <int> to set how old an account must be,
+        in days.
+        """
+        self.enabled = True
+        await self._defcon_action(ctx, days=0, action=Action.ENABLED)
         await self.update_channel_topic()
 
     @defcon_group.command(name='disable', aliases=('off', 'd'))
@@ -148,26 +163,7 @@ class Defcon(Cog):
     async def disable_command(self, ctx: Context) -> None:
         """Disable DEFCON mode. Useful in a pinch, but be sure you know what you're doing!"""
         self.enabled = False
-
-        try:
-            await self.bot.api_client.put(
-                'bot/bot-settings/defcon',
-                json={
-                    'data': {
-                        'days': 0,
-                        'enabled': False
-                    },
-                    'name': 'defcon'
-                }
-            )
-        except Exception as e:
-            log.exception("Unable to update DEFCON settings.")
-            await ctx.send(self.build_defcon_msg("disabled", e))
-            await self.send_defcon_log("disabled", ctx.author, e)
-        else:
-            await ctx.send(self.build_defcon_msg("disabled"))
-            await self.send_defcon_log("disabled", ctx.author)
-
+        await self._defcon_action(ctx, days=0, action=Action.DISABLED)
         await self.update_channel_topic()
 
     @defcon_group.command(name='status', aliases=('s',))
@@ -187,30 +183,8 @@ class Defcon(Cog):
     async def days_command(self, ctx: Context, days: int) -> None:
         """Set how old an account must be to join the server, in days, with DEFCON mode enabled."""
         self.days = timedelta(days=days)
-
-        try:
-            await self.bot.api_client.put(
-                'bot/bot-settings/defcon',
-                json={
-                    'data': {
-                        'days': days,
-                        'enabled': True
-                    },
-                    'name': 'defcon'
-                }
-            )
-        except Exception as e:
-            log.exception("Unable to update DEFCON settings.")
-            await ctx.send(self.build_defcon_msg("updated", e))
-            await self.send_defcon_log("updated", ctx.author, e)
-        else:
-            await ctx.send(self.build_defcon_msg("updated"))
-            await self.send_defcon_log("updated", ctx.author)
-
-        # Enable DEFCON if it's not already
-        if not self.enabled:
-            self.enabled = True
-
+        self.enabled = True
+        await self._defcon_action(ctx, days=days, action=Action.UPDATED)
         await self.update_channel_topic()
 
     async def update_channel_topic(self) -> None:
@@ -224,20 +198,16 @@ class Defcon(Cog):
         self.mod_log.ignore(Event.guild_channel_update, Channels.defcon)
         await self.channel.edit(topic=new_topic)
 
-    def build_defcon_msg(self, change: str, e: Exception = None) -> str:
-        """
-        Build in-channel response string for DEFCON action.
-
-        `change` string may be one of the following: ('enabled', 'disabled', 'updated')
-        """
-        if change.lower() == "enabled":
+    def build_defcon_msg(self, action: Action, e: Exception = None) -> str:
+        """Build in-channel response string for DEFCON action."""
+        if action is Action.ENABLED:
             msg = f"{Emojis.defcon_enabled} DEFCON enabled.\n\n"
-        elif change.lower() == "disabled":
+        elif action is Action.DISABLED:
             msg = f"{Emojis.defcon_disabled} DEFCON disabled.\n\n"
-        elif change.lower() == "updated":
+        elif action is Action.UPDATED:
             msg = (
-                f"{Emojis.defcon_updated} DEFCON days updated; accounts must be {self.days} "
-                "days old to join the server.\n\n"
+                f"{Emojis.defcon_updated} DEFCON days updated; accounts must be {self.days.days} "
+                f"day{'s' if self.days.days > 1 else ''} old to join the server.\n\n"
             )
 
         if e:
@@ -248,28 +218,14 @@ class Defcon(Cog):
 
         return msg
 
-    async def send_defcon_log(self, change: str, actor: Member, e: Exception = None) -> None:
-        """
-        Send log message for DEFCON action.
-
-        `change` string may be one of the following: ('enabled', 'disabled', 'updated')
-        """
-        log_msg = f"**Staffer:** {actor.name}#{actor.discriminator} (`{actor.id}`)\n"
-
-        if change.lower() == "enabled":
-            icon = Icons.defcon_enabled
-            color = Colours.soft_green
-            status_msg = "DEFCON enabled"
-            log_msg += f"**Days:** {self.days.days}\n\n"
-        elif change.lower() == "disabled":
-            icon = Icons.defcon_disabled
-            color = Colours.soft_red
-            status_msg = "DEFCON enabled"
-        elif change.lower() == "updated":
-            icon = Icons.defcon_updated
-            color = Colour.blurple()
-            status_msg = "DEFCON updated"
-            log_msg += f"**Days:** {self.days.days}\n\n"
+    async def send_defcon_log(self, action: Action, actor: Member, e: Exception = None) -> None:
+        """Send log message for DEFCON action."""
+        info = action.value
+        log_msg: str = (
+            f"**Staffer:** {actor.mention} {actor} (`{actor.id}`)\n"
+            f"{info.template.format(days=self.days.days)}"
+        )
+        status_msg = f"DEFCON {action.name.lower()}"
 
         if e:
             log_msg += (
@@ -277,10 +233,9 @@ class Defcon(Cog):
                 f"```py\n{e}\n```"
             )
 
-        await self.mod_log.send_log_message(icon, color, status_msg, log_msg)
+        await self.mod_log.send_log_message(info.icon, info.color, status_msg, log_msg)
 
 
 def setup(bot: Bot) -> None:
-    """DEFCON cog load."""
+    """Load the Defcon cog."""
     bot.add_cog(Defcon(bot))
-    log.info("Cog loaded: Defcon")
diff --git a/bot/cogs/doc.py b/bot/cogs/doc.py
index a13464bff..6e7c00b6a 100644
--- a/bot/cogs/doc.py
+++ b/bot/cogs/doc.py
@@ -4,17 +4,22 @@ import logging
 import re
 import textwrap
 from collections import OrderedDict
+from contextlib import suppress
+from types import SimpleNamespace
 from typing import Any, Callable, Optional, Tuple
 
 import discord
 from bs4 import BeautifulSoup
-from bs4.element import PageElement
+from bs4.element import PageElement, Tag
+from discord.errors import NotFound
 from discord.ext import commands
 from markdownify import MarkdownConverter
-from requests import ConnectionError
+from requests import ConnectTimeout, ConnectionError, HTTPError
 from sphinx.ext import intersphinx
+from urllib3.exceptions import ProtocolError
 
-from bot.constants import MODERATION_ROLES
+from bot.bot import Bot
+from bot.constants import MODERATION_ROLES, RedirectOutput
 from bot.converters import ValidPythonIdentifier, ValidURL
 from bot.decorators import with_role
 from bot.pagination import LinePaginator
@@ -23,10 +28,43 @@ from bot.pagination import LinePaginator
 log = logging.getLogger(__name__)
 logging.getLogger('urllib3').setLevel(logging.WARNING)
 
-
-UNWANTED_SIGNATURE_SYMBOLS = ('[source]', '¶')
+# Since Intersphinx is intended to be used with Sphinx,
+# we need to mock its configuration.
+SPHINX_MOCK_APP = SimpleNamespace(
+    config=SimpleNamespace(
+        intersphinx_timeout=3,
+        tls_verify=True,
+        user_agent="python3:python-discord/bot:1.0.0"
+    )
+)
+
+NO_OVERRIDE_GROUPS = (
+    "2to3fixer",
+    "token",
+    "label",
+    "pdbcommand",
+    "term",
+)
+NO_OVERRIDE_PACKAGES = (
+    "python",
+)
+
+SEARCH_END_TAG_ATTRS = (
+    "data",
+    "function",
+    "class",
+    "exception",
+    "seealso",
+    "section",
+    "rubric",
+    "sphinxsidebar",
+)
+UNWANTED_SIGNATURE_SYMBOLS_RE = re.compile(r"\[source]|\\\\|¶")
 WHITESPACE_AFTER_NEWLINES_RE = re.compile(r"(?<=\n\n)(\s+)")
 
+FAILED_REQUEST_RETRY_AMOUNT = 3
+NOT_FOUND_DELETE_DELAY = RedirectOutput.delete_delay
+
 
 def async_cache(max_size: int = 128, arg_offset: int = 0) -> Callable:
     """
@@ -75,18 +113,6 @@ def markdownify(html: str) -> DocMarkdownConverter:
     return DocMarkdownConverter(bullets='•').convert(html)
 
 
-class DummyObject(object):
-    """A dummy object which supports assigning anything, which the builtin `object()` does not support normally."""
-
-
-class SphinxConfiguration:
-    """Dummy configuration for use with intersphinx."""
-
-    config = DummyObject()
-    config.intersphinx_timeout = 3
-    config.tls_verify = True
-
-
 class InventoryURL(commands.Converter):
     """
     Represents an Intersphinx inventory URL.
@@ -101,7 +127,7 @@ class InventoryURL(commands.Converter):
     async def convert(ctx: commands.Context, url: str) -> str:
         """Convert url to Intersphinx inventory URL."""
         try:
-            intersphinx.fetch_inventory(SphinxConfiguration(), '', url)
+            intersphinx.fetch_inventory(SPHINX_MOCK_APP, '', url)
         except AttributeError:
             raise commands.BadArgument(f"Failed to fetch Intersphinx inventory from URL `{url}`.")
         except ConnectionError:
@@ -121,10 +147,11 @@ class InventoryURL(commands.Converter):
 class Doc(commands.Cog):
     """A set of commands for querying & displaying documentation."""
 
-    def __init__(self, bot: commands.Bot):
+    def __init__(self, bot: Bot):
         self.base_urls = {}
         self.bot = bot
         self.inventories = {}
+        self.renamed_symbols = set()
 
         self.bot.loop.create_task(self.init_refresh_inventory())
 
@@ -134,7 +161,7 @@ class Doc(commands.Cog):
         await self.refresh_inventory()
 
     async def update_single(
-        self, package_name: str, base_url: str, inventory_url: str, config: SphinxConfiguration
+        self, package_name: str, base_url: str, inventory_url: str
     ) -> None:
         """
         Rebuild the inventory for a single package.
@@ -145,18 +172,35 @@ class Doc(commands.Cog):
                 absolute paths that link to specific symbols
             * `inventory_url` is the absolute URL to the intersphinx inventory, fetched by running
                 `intersphinx.fetch_inventory` in an executor on the bot's event loop
-            * `config` is a `SphinxConfiguration` instance to mock the regular sphinx
-                project layout, required for use with intersphinx
         """
         self.base_urls[package_name] = base_url
 
-        fetch_func = functools.partial(intersphinx.fetch_inventory, config, '', inventory_url)
-        for _, value in (await self.bot.loop.run_in_executor(None, fetch_func)).items():
-            # Each value has a bunch of information in the form
-            # `(package_name, version, relative_url, ???)`, and we only
-            # need the relative documentation URL.
-            for symbol, (_, _, relative_doc_url, _) in value.items():
+        package = await self._fetch_inventory(inventory_url)
+        if not package:
+            return None
+
+        for group, value in package.items():
+            for symbol, (package_name, _version, relative_doc_url, _) in value.items():
                 absolute_doc_url = base_url + relative_doc_url
+
+                if symbol in self.inventories:
+                    group_name = group.split(":")[1]
+                    symbol_base_url = self.inventories[symbol].split("/", 3)[2]
+                    if (
+                        group_name in NO_OVERRIDE_GROUPS
+                        or any(package in symbol_base_url for package in NO_OVERRIDE_PACKAGES)
+                    ):
+
+                        symbol = f"{group_name}.{symbol}"
+                        # If renamed `symbol` already exists, add library name in front to differentiate between them.
+                        if symbol in self.renamed_symbols:
+                            # Split `package_name` because of packages like Pillow that have spaces in them.
+                            symbol = f"{package_name.split()[0]}.{symbol}"
+
+                        self.inventories[symbol] = absolute_doc_url
+                        self.renamed_symbols.add(symbol)
+                        continue
+
                 self.inventories[symbol] = absolute_doc_url
 
         log.trace(f"Fetched inventory for {package_name}.")
@@ -170,31 +214,27 @@ class Doc(commands.Cog):
         # Also, reset the cache used for fetching documentation.
         self.base_urls.clear()
         self.inventories.clear()
+        self.renamed_symbols.clear()
         async_cache.cache = OrderedDict()
 
-        # Since Intersphinx is intended to be used with Sphinx,
-        # we need to mock its configuration.
-        config = SphinxConfiguration()
-
         # Run all coroutines concurrently - since each of them performs a HTTP
         # request, this speeds up fetching the inventory data heavily.
         coros = [
             self.update_single(
-                package["package"], package["base_url"], package["inventory_url"], config
+                package["package"], package["base_url"], package["inventory_url"]
             ) for package in await self.bot.api_client.get('bot/documentation-links')
         ]
         await asyncio.gather(*coros)
 
-    async def get_symbol_html(self, symbol: str) -> Optional[Tuple[str, str]]:
+    async def get_symbol_html(self, symbol: str) -> Optional[Tuple[list, str]]:
         """
         Given a Python symbol, return its signature and description.
 
-        Returns a tuple in the form (str, str), or `None`.
-
         The first tuple element is the signature of the given symbol as a markup-free string, and
         the second tuple element is the description of the given symbol with HTML markup included.
 
-        If the given symbol could not be found, returns `None`.
+        If the given symbol is a module, returns a tuple `(None, str)`
+        else if the symbol could not be found, returns `None`.
         """
         url = self.inventories.get(symbol)
         if url is None:
@@ -207,21 +247,38 @@ class Doc(commands.Cog):
         symbol_id = url.split('#')[-1]
         soup = BeautifulSoup(html, 'lxml')
         symbol_heading = soup.find(id=symbol_id)
-        signature_buffer = []
+        search_html = str(soup)
 
         if symbol_heading is None:
             return None
 
-        # Traverse the tags of the signature header and ignore any
-        # unwanted symbols from it. Add all of it to a temporary buffer.
-        for tag in symbol_heading.strings:
-            if tag not in UNWANTED_SIGNATURE_SYMBOLS:
-                signature_buffer.append(tag.replace('\\', ''))
+        if symbol_id == f"module-{symbol}":
+            # Get page content from the module headerlink to the
+            # first tag that has its class in `SEARCH_END_TAG_ATTRS`
+            start_tag = symbol_heading.find("a", attrs={"class": "headerlink"})
+            if start_tag is None:
+                return [], ""
+
+            end_tag = start_tag.find_next(self._match_end_tag)
+            if end_tag is None:
+                return [], ""
 
-        signature = ''.join(signature_buffer)
-        description = str(symbol_heading.next_sibling.next_sibling).replace('¶', '')
+            description_start_index = search_html.find(str(start_tag.parent)) + len(str(start_tag.parent))
+            description_end_index = search_html.find(str(end_tag))
+            description = search_html[description_start_index:description_end_index]
+            signatures = None
 
-        return signature, description
+        else:
+            signatures = []
+            description = str(symbol_heading.find_next_sibling("dd"))
+            description_pos = search_html.find(description)
+            # Get text of up to 3 signatures, remove unwanted symbols
+            for element in [symbol_heading] + symbol_heading.find_next_siblings("dt", limit=2):
+                signature = UNWANTED_SIGNATURE_SYMBOLS_RE.sub("", element.text)
+                if signature and search_html.find(str(element)) < description_pos:
+                    signatures.append(signature)
+
+        return signatures, description.replace('¶', '')
 
     @async_cache(arg_offset=1)
     async def get_symbol_embed(self, symbol: str) -> Optional[discord.Embed]:
@@ -234,7 +291,7 @@ class Doc(commands.Cog):
         if scraped_html is None:
             return None
 
-        signature = scraped_html[0]
+        signatures = scraped_html[0]
         permalink = self.inventories[symbol]
         description = markdownify(scraped_html[1])
 
@@ -242,26 +299,48 @@ class Doc(commands.Cog):
         # of a double newline (interpreted as a paragraph) before index 1000.
         if len(description) > 1000:
             shortened = description[:1000]
-            last_paragraph_end = shortened.rfind('\n\n')
-            description = description[:last_paragraph_end] + f"... [read more]({permalink})"
+            description_cutoff = shortened.rfind('\n\n', 100)
+            if description_cutoff == -1:
+                # Search the shortened version for cutoff points in decreasing desirability,
+                # cutoff at 1000 if none are found.
+                for string in (". ", ", ", ",", " "):
+                    description_cutoff = shortened.rfind(string)
+                    if description_cutoff != -1:
+                        break
+                else:
+                    description_cutoff = 1000
+            description = description[:description_cutoff]
+
+            # If there is an incomplete code block, cut it out
+            if description.count("```") % 2:
+                codeblock_start = description.rfind('```py')
+                description = description[:codeblock_start].rstrip()
+            description += f"... [read more]({permalink})"
 
         description = WHITESPACE_AFTER_NEWLINES_RE.sub('', description)
+        if signatures is None:
+            # If symbol is a module, don't show signature.
+            embed_description = description
 
-        if not signature:
+        elif not signatures:
             # It's some "meta-page", for example:
             # https://docs.djangoproject.com/en/dev/ref/views/#module-django.views
-            return discord.Embed(
-                title=f'`{symbol}`',
-                url=permalink,
-                description="This appears to be a generic page not tied to a specific symbol."
-            )
+            embed_description = "This appears to be a generic page not tied to a specific symbol."
+
+        else:
+            embed_description = "".join(f"```py\n{textwrap.shorten(signature, 500)}```" for signature in signatures)
+            embed_description += f"\n{description}"
 
-        signature = textwrap.shorten(signature, 500)
-        return discord.Embed(
+        embed = discord.Embed(
             title=f'`{symbol}`',
             url=permalink,
-            description=f"```py\n{signature}```{description}"
+            description=embed_description
+        )
+        # Show all symbols with the same name that were renamed in the footer.
+        embed.set_footer(
+            text=", ".join(renamed for renamed in self.renamed_symbols - {symbol} if renamed.endswith(f".{symbol}"))
         )
+        return embed
 
     @commands.group(name='docs', aliases=('doc', 'd'), invoke_without_command=True)
     async def docs_group(self, ctx: commands.Context, symbol: commands.clean_content = None) -> None:
@@ -307,7 +386,10 @@ class Doc(commands.Cog):
                     description=f"Sorry, I could not find any documentation for `{symbol}`.",
                     colour=discord.Colour.red()
                 )
-                await ctx.send(embed=error_embed)
+                error_message = await ctx.send(embed=error_embed)
+                with suppress(NotFound):
+                    await error_message.delete(delay=NOT_FOUND_DELETE_DELAY)
+                    await ctx.message.delete(delay=NOT_FOUND_DELETE_DELAY)
             else:
                 await ctx.send(embed=doc_embed)
 
@@ -336,8 +418,7 @@ class Doc(commands.Cog):
         await self.bot.api_client.post('bot/documentation-links', json=body)
 
         log.info(
-            f"User @{ctx.author.name}#{ctx.author.discriminator} ({ctx.author.id}) "
-            "added a new documentation package:\n"
+            f"User @{ctx.author} ({ctx.author.id}) added a new documentation package:\n"
             f"Package name: {package_name}\n"
             f"Base url: {base_url}\n"
             f"Inventory URL: {inventory_url}"
@@ -366,8 +447,65 @@ class Doc(commands.Cog):
             await self.refresh_inventory()
         await ctx.send(f"Successfully deleted `{package_name}` and refreshed inventory.")
 
+    @docs_group.command(name="refresh", aliases=("rfsh", "r"))
+    @with_role(*MODERATION_ROLES)
+    async def refresh_command(self, ctx: commands.Context) -> None:
+        """Refresh inventories and send differences to channel."""
+        old_inventories = set(self.base_urls)
+        with ctx.typing():
+            await self.refresh_inventory()
+        # Get differences of added and removed inventories
+        added = ', '.join(inv for inv in self.base_urls if inv not in old_inventories)
+        if added:
+            added = f"+ {added}"
+
+        removed = ', '.join(inv for inv in old_inventories if inv not in self.base_urls)
+        if removed:
+            removed = f"- {removed}"
+
+        embed = discord.Embed(
+            title="Inventories refreshed",
+            description=f"```diff\n{added}\n{removed}```" if added or removed else ""
+        )
+        await ctx.send(embed=embed)
+
+    async def _fetch_inventory(self, inventory_url: str) -> Optional[dict]:
+        """Get and return inventory from `inventory_url`. If fetching fails, return None."""
+        fetch_func = functools.partial(intersphinx.fetch_inventory, SPHINX_MOCK_APP, '', inventory_url)
+        for retry in range(1, FAILED_REQUEST_RETRY_AMOUNT+1):
+            try:
+                package = await self.bot.loop.run_in_executor(None, fetch_func)
+            except ConnectTimeout:
+                log.error(
+                    f"Fetching of inventory {inventory_url} timed out,"
+                    f" trying again. ({retry}/{FAILED_REQUEST_RETRY_AMOUNT})"
+                )
+            except ProtocolError:
+                log.error(
+                    f"Connection lost while fetching inventory {inventory_url},"
+                    f" trying again. ({retry}/{FAILED_REQUEST_RETRY_AMOUNT})"
+                )
+            except HTTPError as e:
+                log.error(f"Fetching of inventory {inventory_url} failed with status code {e.response.status_code}.")
+                return None
+            except ConnectionError:
+                log.error(f"Couldn't establish connection to inventory {inventory_url}.")
+                return None
+            else:
+                return package
+        log.error(f"Fetching of inventory {inventory_url} failed.")
+        return None
+
+    @staticmethod
+    def _match_end_tag(tag: Tag) -> bool:
+        """Matches `tag` if its class value is in `SEARCH_END_TAG_ATTRS` or the tag is table."""
+        for attr in SEARCH_END_TAG_ATTRS:
+            if attr in tag.get("class", ()):
+                return True
+
+        return tag.name == "table"
+
 
-def setup(bot: commands.Bot) -> None:
-    """Doc cog load."""
+def setup(bot: Bot) -> None:
+    """Load the Doc cog."""
     bot.add_cog(Doc(bot))
-    log.info("Cog loaded: Doc")
diff --git a/bot/cogs/duck_pond.py b/bot/cogs/duck_pond.py
new file mode 100644
index 000000000..345d2856c
--- /dev/null
+++ b/bot/cogs/duck_pond.py
@@ -0,0 +1,182 @@
+import logging
+from typing import Optional, Union
+
+import discord
+from discord import Color, Embed, Member, Message, RawReactionActionEvent, User, errors
+from discord.ext.commands import Cog
+
+from bot import constants
+from bot.bot import Bot
+from bot.utils.messages import send_attachments
+
+log = logging.getLogger(__name__)
+
+
+class DuckPond(Cog):
+    """Relays messages to #duck-pond whenever a certain number of duck reactions have been achieved."""
+
+    def __init__(self, bot: Bot):
+        self.bot = bot
+        self.webhook_id = constants.Webhooks.duck_pond
+        self.bot.loop.create_task(self.fetch_webhook())
+
+    async def fetch_webhook(self) -> None:
+        """Fetches the webhook object, so we can post to it."""
+        await self.bot.wait_until_ready()
+
+        try:
+            self.webhook = await self.bot.fetch_webhook(self.webhook_id)
+        except discord.HTTPException:
+            log.exception(f"Failed to fetch webhook with id `{self.webhook_id}`")
+
+    @staticmethod
+    def is_staff(member: Union[User, Member]) -> bool:
+        """Check if a specific member or user is staff."""
+        if hasattr(member, "roles"):
+            for role in member.roles:
+                if role.id in constants.STAFF_ROLES:
+                    return True
+        return False
+
+    async def has_green_checkmark(self, message: Message) -> bool:
+        """Check if the message has a green checkmark reaction."""
+        for reaction in message.reactions:
+            if reaction.emoji == "✅":
+                async for user in reaction.users():
+                    if user == self.bot.user:
+                        return True
+        return False
+
+    async def send_webhook(
+        self,
+        content: Optional[str] = None,
+        username: Optional[str] = None,
+        avatar_url: Optional[str] = None,
+        embed: Optional[Embed] = None,
+    ) -> None:
+        """Send a webhook to the duck_pond channel."""
+        try:
+            await self.webhook.send(
+                content=content,
+                username=username,
+                avatar_url=avatar_url,
+                embed=embed
+            )
+        except discord.HTTPException:
+            log.exception("Failed to send a message to the Duck Pool webhook")
+
+    async def count_ducks(self, message: Message) -> int:
+        """
+        Count the number of ducks in the reactions of a specific message.
+
+        Only counts ducks added by staff members.
+        """
+        duck_count = 0
+        duck_reactors = []
+
+        for reaction in message.reactions:
+            async for user in reaction.users():
+
+                # Is the user a staff member and not already counted as reactor?
+                if not self.is_staff(user) or user.id in duck_reactors:
+                    continue
+
+                # Is the emoji a duck?
+                if hasattr(reaction.emoji, "id"):
+                    if reaction.emoji.id in constants.DuckPond.custom_emojis:
+                        duck_count += 1
+                        duck_reactors.append(user.id)
+                elif isinstance(reaction.emoji, str):
+                    if reaction.emoji == "🦆":
+                        duck_count += 1
+                        duck_reactors.append(user.id)
+        return duck_count
+
+    async def relay_message(self, message: Message) -> None:
+        """Relays the message's content and attachments to the duck pond channel."""
+        clean_content = message.clean_content
+
+        if clean_content:
+            await self.send_webhook(
+                content=message.clean_content,
+                username=message.author.display_name,
+                avatar_url=message.author.avatar_url
+            )
+
+        if message.attachments:
+            try:
+                await send_attachments(message, self.webhook)
+            except (errors.Forbidden, errors.NotFound):
+                e = Embed(
+                    description=":x: **This message contained an attachment, but it could not be retrieved**",
+                    color=Color.red()
+                )
+                await self.send_webhook(
+                    embed=e,
+                    username=message.author.display_name,
+                    avatar_url=message.author.avatar_url
+                )
+            except discord.HTTPException:
+                log.exception(f"Failed to send an attachment to the webhook")
+
+        await message.add_reaction("✅")
+
+    @staticmethod
+    def _payload_has_duckpond_emoji(payload: RawReactionActionEvent) -> bool:
+        """Test if the RawReactionActionEvent payload contains a duckpond emoji."""
+        if payload.emoji.is_custom_emoji():
+            if payload.emoji.id in constants.DuckPond.custom_emojis:
+                return True
+        elif payload.emoji.name == "🦆":
+            return True
+
+        return False
+
+    @Cog.listener()
+    async def on_raw_reaction_add(self, payload: RawReactionActionEvent) -> None:
+        """
+        Determine if a message should be sent to the duck pond.
+
+        This will count the number of duck reactions on the message, and if this amount meets the
+        amount of ducks specified in the config under duck_pond/threshold, it will
+        send the message off to the duck pond.
+        """
+        # Is the emoji in the reaction a duck?
+        if not self._payload_has_duckpond_emoji(payload):
+            return
+
+        channel = discord.utils.get(self.bot.get_all_channels(), id=payload.channel_id)
+        message = await channel.fetch_message(payload.message_id)
+        member = discord.utils.get(message.guild.members, id=payload.user_id)
+
+        # Is the member a human and a staff member?
+        if not self.is_staff(member) or member.bot:
+            return
+
+        # Does the message already have a green checkmark?
+        if await self.has_green_checkmark(message):
+            return
+
+        # Time to count our ducks!
+        duck_count = await self.count_ducks(message)
+
+        # If we've got more than the required amount of ducks, send the message to the duck_pond.
+        if duck_count >= constants.DuckPond.threshold:
+            await self.relay_message(message)
+
+    @Cog.listener()
+    async def on_raw_reaction_remove(self, payload: RawReactionActionEvent) -> None:
+        """Ensure that people don't remove the green checkmark from duck ponded messages."""
+        channel = discord.utils.get(self.bot.get_all_channels(), id=payload.channel_id)
+
+        # Prevent the green checkmark from being removed
+        if payload.emoji.name == "✅":
+            message = await channel.fetch_message(payload.message_id)
+            duck_count = await self.count_ducks(message)
+            if duck_count >= constants.DuckPond.threshold:
+                await message.add_reaction("✅")
+
+
+def setup(bot: Bot) -> None:
+    """Load the DuckPond cog."""
+    bot.add_cog(DuckPond(bot))
diff --git a/bot/cogs/error_handler.py b/bot/cogs/error_handler.py
index 49411814c..52893b2ee 100644
--- a/bot/cogs/error_handler.py
+++ b/bot/cogs/error_handler.py
@@ -14,9 +14,10 @@ from discord.ext.commands import (
     NoPrivateMessage,
     UserInputError,
 )
-from discord.ext.commands import Bot, Cog, Context
+from discord.ext.commands import Cog, Context
 
 from bot.api import ResponseCodeError
+from bot.bot import Bot
 from bot.constants import Channels
 from bot.decorators import InChannelCheckFailure
 
@@ -75,6 +76,16 @@ class ErrorHandler(Cog):
                 tags_get_command = self.bot.get_command("tags get")
                 ctx.invoked_from_error_handler = True
 
+                log_msg = "Cancelling attempt to fall back to a tag due to failed checks."
+                try:
+                    if not await tags_get_command.can_run(ctx):
+                        log.debug(log_msg)
+                        return
+                except CommandError as tag_error:
+                    log.debug(log_msg)
+                    await self.on_command_error(ctx, tag_error)
+                    return
+
                 # Return to not raise the exception
                 with contextlib.suppress(ResponseCodeError):
                     await ctx.invoke(tags_get_command, tag_name=ctx.invoked_with)
@@ -143,6 +154,5 @@ class ErrorHandler(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Error handler cog load."""
+    """Load the ErrorHandler cog."""
     bot.add_cog(ErrorHandler(bot))
-    log.info("Cog loaded: Events")
diff --git a/bot/cogs/eval.py b/bot/cogs/eval.py
index 9ce854f2c..9c729f28a 100644
--- a/bot/cogs/eval.py
+++ b/bot/cogs/eval.py
@@ -9,8 +9,9 @@ from io import StringIO
 from typing import Any, Optional, Tuple
 
 import discord
-from discord.ext.commands import Bot, Cog, Context, group
+from discord.ext.commands import Cog, Context, group
 
+from bot.bot import Bot
 from bot.constants import Roles
 from bot.decorators import with_role
 from bot.interpreter import Interpreter
@@ -148,7 +149,7 @@ class CodeEval(Cog):
         self.env.update(env)
 
         # Ignore this code, it works
-        _code = """
+        code_ = """
 async def func():  # (None,) -> Any
     try:
         with contextlib.redirect_stdout(self.stdout):
@@ -162,7 +163,7 @@ async def func():  # (None,) -> Any
 """.format(textwrap.indent(code, '            '))
 
         try:
-            exec(_code, self.env)  # noqa: B102,S102
+            exec(code_, self.env)  # noqa: B102,S102
             func = self.env['func']
             res = await func()
 
@@ -197,6 +198,5 @@ async def func():  # (None,) -> Any
 
 
 def setup(bot: Bot) -> None:
-    """Code eval cog load."""
+    """Load the CodeEval cog."""
     bot.add_cog(CodeEval(bot))
-    log.info("Cog loaded: Eval")
diff --git a/bot/cogs/extensions.py b/bot/cogs/extensions.py
index bb66e0b8e..f16e79fb7 100644
--- a/bot/cogs/extensions.py
+++ b/bot/cogs/extensions.py
@@ -6,8 +6,9 @@ from pkgutil import iter_modules
 
 from discord import Colour, Embed
 from discord.ext import commands
-from discord.ext.commands import Bot, Context, group
+from discord.ext.commands import Context, group
 
+from bot.bot import Bot
 from bot.constants import Emojis, MODERATION_ROLES, Roles, URLs
 from bot.pagination import LinePaginator
 from bot.utils.checks import with_role_check
@@ -233,4 +234,3 @@ class Extensions(commands.Cog):
 def setup(bot: Bot) -> None:
     """Load the Extensions cog."""
     bot.add_cog(Extensions(bot))
-    log.info("Cog loaded: Extensions")
diff --git a/bot/cogs/filtering.py b/bot/cogs/filtering.py
index 265ae5160..74538542a 100644
--- a/bot/cogs/filtering.py
+++ b/bot/cogs/filtering.py
@@ -5,11 +5,12 @@ from typing import Optional, Union
 import discord.errors
 from dateutil.relativedelta import relativedelta
 from discord import Colour, DMChannel, Member, Message, TextChannel
-from discord.ext.commands import Bot, Cog
+from discord.ext.commands import Cog
 
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
 from bot.constants import (
-    Channels, Colours, DEBUG_MODE,
+    Channels, Colours,
     Filter, Icons, URLs
 )
 
@@ -43,7 +44,7 @@ class Filtering(Cog):
     def __init__(self, bot: Bot):
         self.bot = bot
 
-        _staff_mistake_str = "If you believe this was a mistake, please let staff know!"
+        staff_mistake_str = "If you believe this was a mistake, please let staff know!"
         self.filters = {
             "filter_zalgo": {
                 "enabled": Filter.filter_zalgo,
@@ -53,7 +54,7 @@ class Filtering(Cog):
                 "user_notification": Filter.notify_user_zalgo,
                 "notification_msg": (
                     "Your post has been removed for abusing Unicode character rendering (aka Zalgo text). "
-                    f"{_staff_mistake_str}"
+                    f"{staff_mistake_str}"
                 )
             },
             "filter_invites": {
@@ -63,7 +64,7 @@ class Filtering(Cog):
                 "content_only": True,
                 "user_notification": Filter.notify_user_invites,
                 "notification_msg": (
-                    f"Per Rule 10, your invite link has been removed. {_staff_mistake_str}\n\n"
+                    f"Per Rule 6, your invite link has been removed. {staff_mistake_str}\n\n"
                     r"Our server rules can be found here: <https://pythondiscord.com/pages/rules>"
                 )
             },
@@ -74,7 +75,7 @@ class Filtering(Cog):
                 "content_only": True,
                 "user_notification": Filter.notify_user_domains,
                 "notification_msg": (
-                    f"Your URL has been removed because it matched a blacklisted domain. {_staff_mistake_str}"
+                    f"Your URL has been removed because it matched a blacklisted domain. {staff_mistake_str}"
                 )
             },
             "watch_rich_embeds": {
@@ -136,10 +137,6 @@ class Filtering(Cog):
             and not msg.author.bot                          # Author not a bot
         )
 
-        # If we're running the bot locally, ignore role whitelist and only listen to #dev-test
-        if DEBUG_MODE:
-            filter_message = not msg.author.bot and msg.channel.id == Channels.devtest
-
         # If none of the above, we can start filtering.
         if filter_message:
             for filter_name, _filter in self.filters.items():
@@ -154,11 +151,11 @@ class Filtering(Cog):
 
                     # Does the filter only need the message content or the full message?
                     if _filter["content_only"]:
-                        triggered = await _filter["function"](msg.content)
+                        match = await _filter["function"](msg.content)
                     else:
-                        triggered = await _filter["function"](msg)
+                        match = await _filter["function"](msg)
 
-                    if triggered:
+                    if match:
                         # If this is a filter (not a watchlist), we should delete the message.
                         if _filter["type"] == "filter":
                             try:
@@ -184,12 +181,23 @@ class Filtering(Cog):
                         else:
                             channel_str = f"in {msg.channel.mention}"
 
+                        # Word and match stats for watch_words and watch_tokens
+                        if filter_name in ("watch_words", "watch_tokens"):
+                            surroundings = match.string[max(match.start() - 10, 0): match.end() + 10]
+                            message_content = (
+                                f"**Match:** '{match[0]}'\n"
+                                f"**Location:** '...{surroundings}...'\n"
+                                f"\n**Original Message:**\n{msg.content}"
+                            )
+                        else:  # Use content of discord Message
+                            message_content = msg.content
+
                         message = (
                             f"The {filter_name} {_filter['type']} was triggered "
-                            f"by **{msg.author.name}#{msg.author.discriminator}** "
+                            f"by **{msg.author}** "
                             f"(`{msg.author.id}`) {channel_str} with [the "
                             f"following message]({msg.jump_url}):\n\n"
-                            f"{msg.content}"
+                            f"{message_content}"
                         )
 
                         log.debug(message)
@@ -199,7 +207,7 @@ class Filtering(Cog):
 
                         if filter_name == "filter_invites":
                             additional_embeds = []
-                            for invite, data in triggered.items():
+                            for invite, data in match.items():
                                 embed = discord.Embed(description=(
                                     f"**Members:**\n{data['members']}\n"
                                     f"**Active:**\n{data['active']}"
@@ -230,31 +238,33 @@ class Filtering(Cog):
                         break  # We don't want multiple filters to trigger
 
     @staticmethod
-    async def _has_watchlist_words(text: str) -> bool:
+    async def _has_watchlist_words(text: str) -> Union[bool, re.Match]:
         """
         Returns True if the text contains one of the regular expressions from the word_watchlist in our filter config.
 
         Only matches words with boundaries before and after the expression.
         """
         for regex_pattern in WORD_WATCHLIST_PATTERNS:
-            if regex_pattern.search(text):
-                return True
+            match = regex_pattern.search(text)
+            if match:
+                return match  # match objects always have a boolean value of True
 
         return False
 
     @staticmethod
-    async def _has_watchlist_tokens(text: str) -> bool:
+    async def _has_watchlist_tokens(text: str) -> Union[bool, re.Match]:
         """
         Returns True if the text contains one of the regular expressions from the token_watchlist in our filter config.
 
         This will match the expression even if it does not have boundaries before and after.
         """
         for regex_pattern in TOKEN_WATCHLIST_PATTERNS:
-            if regex_pattern.search(text):
+            match = regex_pattern.search(text)
+            if match:
 
                 # Make sure it's not a URL
                 if not URL_RE.search(text):
-                    return True
+                    return match  # match objects always have a boolean value of True
 
         return False
 
@@ -361,6 +371,5 @@ class Filtering(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Filtering cog load."""
+    """Load the Filtering cog."""
     bot.add_cog(Filtering(bot))
-    log.info("Cog loaded: Filtering")
diff --git a/bot/cogs/free.py b/bot/cogs/free.py
index 269c5c1b9..49cab6172 100644
--- a/bot/cogs/free.py
+++ b/bot/cogs/free.py
@@ -3,8 +3,9 @@ from datetime import datetime
 from operator import itemgetter
 
 from discord import Colour, Embed, Member, utils
-from discord.ext.commands import Bot, Cog, Context, command
+from discord.ext.commands import Cog, Context, command
 
+from bot.bot import Bot
 from bot.constants import Categories, Channels, Free, STAFF_ROLES
 from bot.decorators import redirect_output
 
@@ -72,35 +73,31 @@ class Free(Cog):
         # Display all potentially inactive channels
         # in descending order of inactivity
         if free_channels:
-            embed.description += "**The following channel{0} look{1} free:**\n\n**".format(
-                's' if len(free_channels) > 1 else '',
-                '' if len(free_channels) > 1 else 's'
-            )
-
             # Sort channels in descending order by seconds
             # Get position in list, inactivity, and channel object
             # For each channel, add to embed.description
             sorted_channels = sorted(free_channels, key=itemgetter(0), reverse=True)
-            for i, (inactive, channel) in enumerate(sorted_channels, 1):
+
+            for (inactive, channel) in sorted_channels[:3]:
                 minutes, seconds = divmod(inactive, 60)
                 if minutes > 59:
                     hours, minutes = divmod(minutes, 60)
-                    embed.description += f"{i}. {channel.mention} inactive for {hours}h{minutes}m{seconds}s\n\n"
+                    embed.description += f"{channel.mention} **{hours}h {minutes}m {seconds}s** inactive\n"
                 else:
-                    embed.description += f"{i}. {channel.mention} inactive for {minutes}m{seconds}s\n\n"
+                    embed.description += f"{channel.mention} **{minutes}m {seconds}s** inactive\n"
 
-            embed.description += ("**\nThese channels aren't guaranteed to be free, "
-                                  "so use your best judgement and check for yourself.")
+            embed.set_footer(text="Please confirm these channels are free before posting")
         else:
-            embed.description = ("**Doesn't look like any channels are available right now. "
-                                 "You're welcome to check for yourself to be sure. "
-                                 "If all channels are truly busy, please be patient "
-                                 "as one will likely be available soon.**")
+            embed.description = (
+                "Doesn't look like any channels are available right now. "
+                "You're welcome to check for yourself to be sure. "
+                "If all channels are truly busy, please be patient "
+                "as one will likely be available soon."
+            )
 
         await ctx.send(embed=embed)
 
 
 def setup(bot: Bot) -> None:
-    """Free cog load."""
+    """Load the Free cog."""
     bot.add_cog(Free())
-    log.info("Cog loaded: Free")
diff --git a/bot/cogs/information.py b/bot/cogs/information.py
index 1afb37103..125d7ce24 100644
--- a/bot/cogs/information.py
+++ b/bot/cogs/information.py
@@ -1,14 +1,21 @@
 import colorsys
 import logging
+import pprint
 import textwrap
 import typing
+from collections import defaultdict
+from typing import Any, Mapping, Optional
 
+import discord
 from discord import CategoryChannel, Colour, Embed, Member, Role, TextChannel, VoiceChannel, utils
-from discord.ext.commands import Bot, Cog, Context, command
-
-from bot.constants import Channels, Emojis, MODERATION_ROLES, STAFF_ROLES
-from bot.decorators import InChannelCheckFailure, with_role
-from bot.utils.checks import with_role_check
+from discord.ext import commands
+from discord.ext.commands import BucketType, Cog, Context, command, group
+from discord.utils import escape_markdown
+
+from bot import constants
+from bot.bot import Bot
+from bot.decorators import InChannelCheckFailure, in_channel, with_role
+from bot.utils.checks import cooldown_with_role_bypass, with_role_check
 from bot.utils.time import time_since
 
 log = logging.getLogger(__name__)
@@ -20,7 +27,7 @@ class Information(Cog):
     def __init__(self, bot: Bot):
         self.bot = bot
 
-    @with_role(*MODERATION_ROLES)
+    @with_role(*constants.MODERATION_ROLES)
     @command(name="roles")
     async def roles_info(self, ctx: Context) -> None:
         """Returns a list of all roles and their corresponding IDs."""
@@ -44,7 +51,7 @@ class Information(Cog):
 
         await ctx.send(embed=embed)
 
-    @with_role(*MODERATION_ROLES)
+    @with_role(*constants.MODERATION_ROLES)
     @command(name="role")
     async def role_info(self, ctx: Context, *roles: typing.Union[Role, str]) -> None:
         """
@@ -144,10 +151,10 @@ class Information(Cog):
                 Channel categories: {category_channels}
 
                 **Members**
-                {Emojis.status_online} {online}
-                {Emojis.status_idle} {idle}
-                {Emojis.status_dnd} {dnd}
-                {Emojis.status_offline} {offline}
+                {constants.Emojis.status_online} {online}
+                {constants.Emojis.status_idle} {idle}
+                {constants.Emojis.status_dnd} {dnd}
+                {constants.Emojis.status_offline} {offline}
             """)
         )
 
@@ -156,81 +163,238 @@ class Information(Cog):
         await ctx.send(embed=embed)
 
     @command(name="user", aliases=["user_info", "member", "member_info"])
-    async def user_info(self, ctx: Context, user: Member = None, hidden: bool = False) -> None:
+    async def user_info(self, ctx: Context, user: Member = None) -> None:
         """Returns info about a user."""
         if user is None:
             user = ctx.author
 
         # Do a role check if this is being executed on someone other than the caller
-        if user != ctx.author and not with_role_check(ctx, *MODERATION_ROLES):
+        if user != ctx.author and not with_role_check(ctx, *constants.MODERATION_ROLES):
             await ctx.send("You may not use this command on users other than yourself.")
             return
 
-        # Non-moderators may only do this in #bot-commands and can't see hidden infractions.
-        if not with_role_check(ctx, *STAFF_ROLES):
-            if not ctx.channel.id == Channels.bot:
-                raise InChannelCheckFailure(Channels.bot)
-            # Hide hidden infractions for users without a moderation role
-            hidden = False
+        # Non-staff may only do this in #bot-commands
+        if not with_role_check(ctx, *constants.STAFF_ROLES):
+            if not ctx.channel.id == constants.Channels.bot:
+                raise InChannelCheckFailure(constants.Channels.bot)
+
+        embed = await self.create_user_embed(ctx, user)
 
-        # User information
+        await ctx.send(embed=embed)
+
+    async def create_user_embed(self, ctx: Context, user: Member) -> Embed:
+        """Creates an embed containing information on the `user`."""
         created = time_since(user.created_at, max_units=3)
 
+        # Custom status
+        custom_status = ''
+        for activity in user.activities:
+            # Check activity.state for None value if user has a custom status set
+            # This guards against a custom status with an emoji but no text, which will cause
+            # escape_markdown to raise an exception
+            # This can be reworked after a move to d.py 1.3.0+, which adds a CustomActivity class
+            if activity.name == 'Custom Status' and activity.state:
+                state = escape_markdown(activity.state)
+                custom_status = f'Status: {state}\n'
+
         name = str(user)
         if user.nick:
             name = f"{user.nick} ({name})"
 
-        # Member information
         joined = time_since(user.joined_at, precision="days")
-
-        # You're welcome, Volcyyyyyyyyyyyyyyyy
         roles = ", ".join(role.mention for role in user.roles if role.name != "@everyone")
 
-        # Infractions
+        description = [
+            textwrap.dedent(f"""
+                **User Information**
+                Created: {created}
+                Profile: {user.mention}
+                ID: {user.id}
+                {custom_status}
+                **Member Information**
+                Joined: {joined}
+                Roles: {roles or None}
+            """).strip()
+        ]
+
+        # Show more verbose output in moderation channels for infractions and nominations
+        if ctx.channel.id in constants.MODERATION_CHANNELS:
+            description.append(await self.expanded_user_infraction_counts(user))
+            description.append(await self.user_nomination_counts(user))
+        else:
+            description.append(await self.basic_user_infraction_counts(user))
+
+        # Let's build the embed now
+        embed = Embed(
+            title=name,
+            description="\n\n".join(description)
+        )
+
+        embed.set_thumbnail(url=user.avatar_url_as(format="png"))
+        embed.colour = user.top_role.colour if roles else Colour.blurple()
+
+        return embed
+
+    async def basic_user_infraction_counts(self, member: Member) -> str:
+        """Gets the total and active infraction counts for the given `member`."""
         infractions = await self.bot.api_client.get(
             'bot/infractions',
             params={
-                'hidden': str(hidden),
-                'user__id': str(user.id)
+                'hidden': 'False',
+                'user__id': str(member.id)
             }
         )
 
-        infr_total = 0
-        infr_active = 0
+        total_infractions = len(infractions)
+        active_infractions = sum(infraction['active'] for infraction in infractions)
 
-        # At least it's readable.
-        for infr in infractions:
-            if infr["active"]:
-                infr_active += 1
+        infraction_output = f"**Infractions**\nTotal: {total_infractions}\nActive: {active_infractions}"
 
-            infr_total += 1
+        return infraction_output
 
-        # Let's build the embed now
-        embed = Embed(
-            title=name,
-            description=textwrap.dedent(f"""
-                **User Information**
-                Created: {created}
-                Profile: {user.mention}
-                ID: {user.id}
+    async def expanded_user_infraction_counts(self, member: Member) -> str:
+        """
+        Gets expanded infraction counts for the given `member`.
 
-                **Member Information**
-                Joined: {joined}
-                Roles: {roles or None}
+        The counts will be split by infraction type and the number of active infractions for each type will indicated
+        in the output as well.
+        """
+        infractions = await self.bot.api_client.get(
+            'bot/infractions',
+            params={
+                'user__id': str(member.id)
+            }
+        )
 
-                **Infractions**
-                Total: {infr_total}
-                Active: {infr_active}
-            """)
+        infraction_output = ["**Infractions**"]
+        if not infractions:
+            infraction_output.append("This user has never received an infraction.")
+        else:
+            # Count infractions split by `type` and `active` status for this user
+            infraction_types = set()
+            infraction_counter = defaultdict(int)
+            for infraction in infractions:
+                infraction_type = infraction["type"]
+                infraction_active = 'active' if infraction["active"] else 'inactive'
+
+                infraction_types.add(infraction_type)
+                infraction_counter[f"{infraction_active} {infraction_type}"] += 1
+
+            # Format the output of the infraction counts
+            for infraction_type in sorted(infraction_types):
+                active_count = infraction_counter[f"active {infraction_type}"]
+                total_count = active_count + infraction_counter[f"inactive {infraction_type}"]
+
+                line = f"{infraction_type.capitalize()}s: {total_count}"
+                if active_count:
+                    line += f" ({active_count} active)"
+
+                infraction_output.append(line)
+
+        return "\n".join(infraction_output)
+
+    async def user_nomination_counts(self, member: Member) -> str:
+        """Gets the active and historical nomination counts for the given `member`."""
+        nominations = await self.bot.api_client.get(
+            'bot/nominations',
+            params={
+                'user__id': str(member.id)
+            }
         )
 
-        embed.set_thumbnail(url=user.avatar_url_as(format="png"))
-        embed.colour = user.top_role.colour if roles else Colour.blurple()
+        output = ["**Nominations**"]
 
-        await ctx.send(embed=embed)
+        if not nominations:
+            output.append("This user has never been nominated.")
+        else:
+            count = len(nominations)
+            is_currently_nominated = any(nomination["active"] for nomination in nominations)
+            nomination_noun = "nomination" if count == 1 else "nominations"
+
+            if is_currently_nominated:
+                output.append(f"This user is **currently** nominated ({count} {nomination_noun} in total).")
+            else:
+                output.append(f"This user has {count} historical {nomination_noun}, but is currently not nominated.")
+
+        return "\n".join(output)
+
+    def format_fields(self, mapping: Mapping[str, Any], field_width: Optional[int] = None) -> str:
+        """Format a mapping to be readable to a human."""
+        # sorting is technically superfluous but nice if you want to look for a specific field
+        fields = sorted(mapping.items(), key=lambda item: item[0])
+
+        if field_width is None:
+            field_width = len(max(mapping.keys(), key=len))
+
+        out = ''
+
+        for key, val in fields:
+            if isinstance(val, dict):
+                # if we have dicts inside dicts we want to apply the same treatment to the inner dictionaries
+                inner_width = int(field_width * 1.6)
+                val = '\n' + self.format_fields(val, field_width=inner_width)
+
+            elif isinstance(val, str):
+                # split up text since it might be long
+                text = textwrap.fill(val, width=100, replace_whitespace=False)
+
+                # indent it, I guess you could do this with `wrap` and `join` but this is nicer
+                val = textwrap.indent(text, ' ' * (field_width + len(': ')))
+
+                # the first line is already indented so we `str.lstrip` it
+                val = val.lstrip()
+
+            if key == 'color':
+                # makes the base 10 representation of a hex number readable to humans
+                val = hex(val)
+
+            out += '{0:>{width}}: {1}\n'.format(key, val, width=field_width)
+
+        # remove trailing whitespace
+        return out.rstrip()
+
+    @cooldown_with_role_bypass(2, 60 * 3, BucketType.member, bypass_roles=constants.STAFF_ROLES)
+    @group(invoke_without_command=True)
+    @in_channel(constants.Channels.bot, bypass_roles=constants.STAFF_ROLES)
+    async def raw(self, ctx: Context, *, message: discord.Message, json: bool = False) -> None:
+        """Shows information about the raw API response."""
+        # I *guess* it could be deleted right as the command is invoked but I felt like it wasn't worth handling
+        # doing this extra request is also much easier than trying to convert everything back into a dictionary again
+        raw_data = await ctx.bot.http.get_message(message.channel.id, message.id)
+
+        paginator = commands.Paginator()
+
+        def add_content(title: str, content: str) -> None:
+            paginator.add_line(f'== {title} ==\n')
+            # replace backticks as it breaks out of code blocks. Spaces seemed to be the most reasonable solution.
+            # we hope it's not close to 2000
+            paginator.add_line(content.replace('```', '`` `'))
+            paginator.close_page()
+
+        if message.content:
+            add_content('Raw message', message.content)
+
+        transformer = pprint.pformat if json else self.format_fields
+        for field_name in ('embeds', 'attachments'):
+            data = raw_data[field_name]
+
+            if not data:
+                continue
+
+            total = len(data)
+            for current, item in enumerate(data, start=1):
+                title = f'Raw {field_name} ({current}/{total})'
+                add_content(title, transformer(item))
+
+        for page in paginator.pages:
+            await ctx.send(page)
+
+    @raw.command()
+    async def json(self, ctx: Context, message: discord.Message) -> None:
+        """Shows information about the raw API response in a copy-pasteable Python format."""
+        await ctx.invoke(self.raw, message=message, json=True)
 
 
 def setup(bot: Bot) -> None:
-    """Information cog load."""
+    """Load the Information cog."""
     bot.add_cog(Information(bot))
-    log.info("Cog loaded: Information")
diff --git a/bot/cogs/jams.py b/bot/cogs/jams.py
index be9d33e3e..985f28ce5 100644
--- a/bot/cogs/jams.py
+++ b/bot/cogs/jams.py
@@ -4,6 +4,7 @@ from discord import Member, PermissionOverwrite, utils
 from discord.ext import commands
 from more_itertools import unique_everseen
 
+from bot.bot import Bot
 from bot.constants import Roles
 from bot.decorators import with_role
 
@@ -13,7 +14,7 @@ log = logging.getLogger(__name__)
 class CodeJams(commands.Cog):
     """Manages the code-jam related parts of our server."""
 
-    def __init__(self, bot: commands.Bot):
+    def __init__(self, bot: Bot):
         self.bot = bot
 
     @commands.command()
@@ -108,7 +109,6 @@ class CodeJams(commands.Cog):
         )
 
 
-def setup(bot: commands.Bot) -> None:
-    """Code Jams cog load."""
+def setup(bot: Bot) -> None:
+    """Load the CodeJams cog."""
     bot.add_cog(CodeJams(bot))
-    log.info("Cog loaded: CodeJams")
diff --git a/bot/cogs/logging.py b/bot/cogs/logging.py
index c92b619ff..d1b7dcab3 100644
--- a/bot/cogs/logging.py
+++ b/bot/cogs/logging.py
@@ -1,8 +1,9 @@
 import logging
 
 from discord import Embed
-from discord.ext.commands import Bot, Cog
+from discord.ext.commands import Cog
 
+from bot.bot import Bot
 from bot.constants import Channels, DEBUG_MODE
 
 
@@ -37,6 +38,5 @@ class Logging(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Logging cog load."""
+    """Load the Logging cog."""
     bot.add_cog(Logging(bot))
-    log.info("Cog loaded: Logging")
diff --git a/bot/cogs/moderation/__init__.py b/bot/cogs/moderation/__init__.py
index 7383ed44e..5243cb92d 100644
--- a/bot/cogs/moderation/__init__.py
+++ b/bot/cogs/moderation/__init__.py
@@ -1,25 +1,13 @@
-import logging
-
-from discord.ext.commands import Bot
-
+from bot.bot import Bot
 from .infractions import Infractions
 from .management import ModManagement
 from .modlog import ModLog
 from .superstarify import Superstarify
 
-log = logging.getLogger(__name__)
-
 
 def setup(bot: Bot) -> None:
-    """Load the moderation extension (Infractions, ModManagement, ModLog, & Superstarify cogs)."""
+    """Load the Infractions, ModManagement, ModLog, and Superstarify cogs."""
     bot.add_cog(Infractions(bot))
-    log.info("Cog loaded: Infractions")
-
     bot.add_cog(ModLog(bot))
-    log.info("Cog loaded: ModLog")
-
     bot.add_cog(ModManagement(bot))
-    log.info("Cog loaded: ModManagement")
-
     bot.add_cog(Superstarify(bot))
-    log.info("Cog loaded: Superstarify")
diff --git a/bot/cogs/moderation/infractions.py b/bot/cogs/moderation/infractions.py
index 592ead60f..f4e296df9 100644
--- a/bot/cogs/moderation/infractions.py
+++ b/bot/cogs/moderation/infractions.py
@@ -1,91 +1,53 @@
 import logging
-import textwrap
 import typing as t
-from datetime import datetime
 
-import dateutil.parser
 import discord
 from discord import Member
 from discord.ext import commands
 from discord.ext.commands import Context, command
 
 from bot import constants
-from bot.api import ResponseCodeError
-from bot.constants import Colours, Event
+from bot.bot import Bot
+from bot.constants import Event
+from bot.converters import Expiry, FetchedMember
 from bot.decorators import respect_role_hierarchy
-from bot.utils import time
 from bot.utils.checks import with_role_check
-from bot.utils.scheduling import Scheduler
 from . import utils
-from .modlog import ModLog
-from .utils import MemberObject
+from .scheduler import InfractionScheduler
+from .utils import UserSnowflake
 
 log = logging.getLogger(__name__)
 
-MemberConverter = t.Union[utils.UserTypes, utils.proxy_user]
 
-
-class Infractions(Scheduler, commands.Cog):
+class Infractions(InfractionScheduler, commands.Cog):
     """Apply and pardon infractions on users for moderation purposes."""
 
     category = "Moderation"
     category_description = "Server moderation tools."
 
-    def __init__(self, bot: commands.Bot):
-        super().__init__()
+    def __init__(self, bot: Bot):
+        super().__init__(bot, supported_infractions={"ban", "kick", "mute", "note", "warning"})
 
-        self.bot = bot
         self.category = "Moderation"
         self._muted_role = discord.Object(constants.Roles.muted)
 
-        self.bot.loop.create_task(self.reschedule_infractions())
-
-    @property
-    def mod_log(self) -> ModLog:
-        """Get currently loaded ModLog cog instance."""
-        return self.bot.get_cog("ModLog")
-
-    async def reschedule_infractions(self) -> None:
-        """Schedule expiration for previous infractions."""
-        await self.bot.wait_until_ready()
-
-        infractions = await self.bot.api_client.get(
-            'bot/infractions',
-            params={'active': 'true'}
-        )
-        for infraction in infractions:
-            if infraction["expires_at"] is not None:
-                self.schedule_task(self.bot.loop, infraction["id"], infraction)
-
     @commands.Cog.listener()
     async def on_member_join(self, member: Member) -> None:
         """Reapply active mute infractions for returning members."""
         active_mutes = await self.bot.api_client.get(
-            'bot/infractions',
+            "bot/infractions",
             params={
-                'user__id': str(member.id),
-                'type': 'mute',
-                'active': 'true'
+                "active": "true",
+                "type": "mute",
+                "user__id": member.id
             }
         )
-        if not active_mutes:
-            return
 
-        # Assume a single mute because of restrictions elsewhere.
-        mute = active_mutes[0]
+        if active_mutes:
+            reason = f"Re-applying active mute: {active_mutes[0]['id']}"
+            action = member.add_roles(self._muted_role, reason=reason)
 
-        # Calculate the time remaining, in seconds, for the mute.
-        expiry = dateutil.parser.isoparse(mute["expires_at"]).replace(tzinfo=None)
-        delta = (expiry - datetime.utcnow()).total_seconds()
-
-        # Mark as inactive if less than a minute remains.
-        if delta < 60:
-            await self.deactivate_infraction(mute)
-            return
-
-        # Allowing mod log since this is a passive action that should be logged.
-        await member.add_roles(self._muted_role, reason=f"Re-applying active mute: {mute['id']}")
-        log.debug(f"User {member.id} has been re-muted on rejoin.")
+            await self.reapply_infraction(active_mutes[0], action)
 
     # region: Permanent infractions
 
@@ -104,7 +66,7 @@ class Infractions(Scheduler, commands.Cog):
         await self.apply_kick(ctx, user, reason, active=False)
 
     @command()
-    async def ban(self, ctx: Context, user: MemberConverter, *, reason: str = None) -> None:
+    async def ban(self, ctx: Context, user: FetchedMember, *, reason: str = None) -> None:
         """Permanently ban a user for the given reason."""
         await self.apply_ban(ctx, user, reason)
 
@@ -112,7 +74,7 @@ class Infractions(Scheduler, commands.Cog):
     # region: Temporary infractions
 
     @command(aliases=["mute"])
-    async def tempmute(self, ctx: Context, user: Member, duration: utils.Expiry, *, reason: str = None) -> None:
+    async def tempmute(self, ctx: Context, user: Member, duration: Expiry, *, reason: str = None) -> None:
         """
         Temporarily mute a user for the given reason and duration.
 
@@ -131,7 +93,7 @@ class Infractions(Scheduler, commands.Cog):
         await self.apply_mute(ctx, user, reason, expires_at=duration)
 
     @command()
-    async def tempban(self, ctx: Context, user: MemberConverter, duration: utils.Expiry, *, reason: str = None) -> None:
+    async def tempban(self, ctx: Context, user: FetchedMember, duration: Expiry, *, reason: str = None) -> None:
         """
         Temporarily ban a user for the given reason and duration.
 
@@ -153,7 +115,7 @@ class Infractions(Scheduler, commands.Cog):
     # region: Permanent shadow infractions
 
     @command(hidden=True)
-    async def note(self, ctx: Context, user: MemberConverter, *, reason: str = None) -> None:
+    async def note(self, ctx: Context, user: FetchedMember, *, reason: str = None) -> None:
         """Create a private note for a user with the given reason without notifying the user."""
         infraction = await utils.post_infraction(ctx, user, "note", reason, hidden=True, active=False)
         if infraction is None:
@@ -167,7 +129,7 @@ class Infractions(Scheduler, commands.Cog):
         await self.apply_kick(ctx, user, reason, hidden=True, active=False)
 
     @command(hidden=True, aliases=['shadowban', 'sban'])
-    async def shadow_ban(self, ctx: Context, user: MemberConverter, *, reason: str = None) -> None:
+    async def shadow_ban(self, ctx: Context, user: FetchedMember, *, reason: str = None) -> None:
         """Permanently ban a user for the given reason without notifying the user."""
         await self.apply_ban(ctx, user, reason, hidden=True)
 
@@ -175,7 +137,7 @@ class Infractions(Scheduler, commands.Cog):
     # region: Temporary shadow infractions
 
     @command(hidden=True, aliases=["shadowtempmute, stempmute", "shadowmute", "smute"])
-    async def shadow_tempmute(self, ctx: Context, user: Member, duration: utils.Expiry, *, reason: str = None) -> None:
+    async def shadow_tempmute(self, ctx: Context, user: Member, duration: Expiry, *, reason: str = None) -> None:
         """
         Temporarily mute a user for the given reason and duration without notifying the user.
 
@@ -197,8 +159,8 @@ class Infractions(Scheduler, commands.Cog):
     async def shadow_tempban(
         self,
         ctx: Context,
-        user: MemberConverter,
-        duration: utils.Expiry,
+        user: FetchedMember,
+        duration: Expiry,
         *,
         reason: str = None
     ) -> None:
@@ -223,36 +185,41 @@ class Infractions(Scheduler, commands.Cog):
     # region: Remove infractions (un- commands)
 
     @command()
-    async def unmute(self, ctx: Context, user: MemberConverter) -> None:
+    async def unmute(self, ctx: Context, user: FetchedMember) -> None:
         """Prematurely end the active mute infraction for the user."""
         await self.pardon_infraction(ctx, "mute", user)
 
     @command()
-    async def unban(self, ctx: Context, user: MemberConverter) -> None:
+    async def unban(self, ctx: Context, user: FetchedMember) -> None:
         """Prematurely end the active ban infraction for the user."""
         await self.pardon_infraction(ctx, "ban", user)
 
     # endregion
-    # region: Base infraction functions
+    # region: Base apply functions
 
     async def apply_mute(self, ctx: Context, user: Member, reason: str, **kwargs) -> None:
         """Apply a mute infraction with kwargs passed to `post_infraction`."""
         if await utils.has_active_infraction(ctx, user, "mute"):
             return
 
-        infraction = await utils.post_infraction(ctx, user, "mute", reason, **kwargs)
+        infraction = await utils.post_infraction(ctx, user, "mute", reason, active=True, **kwargs)
         if infraction is None:
             return
 
         self.mod_log.ignore(Event.member_update, user.id)
 
-        action = user.add_roles(self._muted_role, reason=reason)
-        await self.apply_infraction(ctx, infraction, user, action)
+        async def action() -> None:
+            await user.add_roles(self._muted_role, reason=reason)
+
+            log.trace(f"Attempting to kick {user} from voice because they've been muted.")
+            await user.move_to(None, reason=reason)
+
+        await self.apply_infraction(ctx, infraction, user, action())
 
     @respect_role_hierarchy()
     async def apply_kick(self, ctx: Context, user: Member, reason: str, **kwargs) -> None:
         """Apply a kick infraction with kwargs passed to `post_infraction`."""
-        infraction = await utils.post_infraction(ctx, user, "kick", reason, **kwargs)
+        infraction = await utils.post_infraction(ctx, user, "kick", reason, active=False, **kwargs)
         if infraction is None:
             return
 
@@ -262,12 +229,12 @@ class Infractions(Scheduler, commands.Cog):
         await self.apply_infraction(ctx, infraction, user, action)
 
     @respect_role_hierarchy()
-    async def apply_ban(self, ctx: Context, user: MemberObject, reason: str, **kwargs) -> None:
+    async def apply_ban(self, ctx: Context, user: UserSnowflake, reason: str, **kwargs) -> None:
         """Apply a ban infraction with kwargs passed to `post_infraction`."""
         if await utils.has_active_infraction(ctx, user, "ban"):
             return
 
-        infraction = await utils.post_infraction(ctx, user, "ban", reason, **kwargs)
+        infraction = await utils.post_infraction(ctx, user, "ban", reason, active=True, **kwargs)
         if infraction is None:
             return
 
@@ -277,319 +244,63 @@ class Infractions(Scheduler, commands.Cog):
         await self.apply_infraction(ctx, infraction, user, action)
 
     # endregion
-    # region: Utility functions
-
-    async def _scheduled_task(self, infraction: utils.Infraction) -> None:
-        """
-        Marks an infraction expired after the delay from time of scheduling to time of expiration.
-
-        At the time of expiration, the infraction is marked as inactive on the website and the
-        expiration task is cancelled.
-        """
-        _id = infraction["id"]
-
-        expiry = dateutil.parser.isoparse(infraction["expires_at"]).replace(tzinfo=None)
-        await time.wait_until(expiry)
-
-        log.debug(f"Marking infraction {_id} as inactive (expired).")
-        await self.deactivate_infraction(infraction)
-
-    async def deactivate_infraction(
-        self,
-        infraction: utils.Infraction,
-        send_log: bool = True
-    ) -> t.Dict[str, str]:
-        """
-        Deactivate an active infraction and return a dictionary of lines to send in a mod log.
-
-        The infraction is removed from Discord, marked as inactive in the database, and has its
-        expiration task cancelled. If `send_log` is True, a mod log is sent for the
-        deactivation of the infraction.
-
-        Supported infraction types are mute and ban. Other types will raise a ValueError.
-        """
-        guild = self.bot.get_guild(constants.Guild.id)
-        mod_role = guild.get_role(constants.Roles.moderator)
-        user_id = infraction["user"]
-        _type = infraction["type"]
-        _id = infraction["id"]
-        reason = f"Infraction #{_id} expired or was pardoned."
-
-        log.debug(f"Marking infraction #{_id} as inactive (expired).")
-
-        log_content = None
-        log_text = {
-            "Member": str(user_id),
-            "Actor": str(self.bot.user),
-            "Reason": infraction["reason"]
-        }
-
-        try:
-            if _type == "mute":
-                user = guild.get_member(user_id)
-                if user:
-                    # Remove the muted role.
-                    self.mod_log.ignore(Event.member_update, user.id)
-                    await user.remove_roles(self._muted_role, reason=reason)
-
-                    # DM the user about the expiration.
-                    notified = await utils.notify_pardon(
-                        user=user,
-                        title="You have been unmuted.",
-                        content="You may now send messages in the server.",
-                        icon_url=utils.INFRACTION_ICONS["mute"][1]
-                    )
-
-                    log_text["Member"] = f"{user.mention}(`{user.id}`)"
-                    log_text["DM"] = "Sent" if notified else "**Failed**"
-                else:
-                    log.info(f"Failed to unmute user {user_id}: user not found")
-                    log_text["Failure"] = "User was not found in the guild."
-            elif _type == "ban":
-                user = discord.Object(user_id)
-                self.mod_log.ignore(Event.member_unban, user_id)
-                try:
-                    await guild.unban(user, reason=reason)
-                except discord.NotFound:
-                    log.info(f"Failed to unban user {user_id}: no active ban found on Discord")
-                    log_text["Note"] = "No active ban found on Discord."
-            else:
-                raise ValueError(
-                    f"Attempted to deactivate an unsupported infraction #{_id} ({_type})!"
-                )
-        except discord.Forbidden:
-            log.warning(f"Failed to deactivate infraction #{_id} ({_type}): bot lacks permissions")
-            log_text["Failure"] = f"The bot lacks permissions to do this (role hierarchy?)"
-            log_content = mod_role.mention
-        except discord.HTTPException as e:
-            log.exception(f"Failed to deactivate infraction #{_id} ({_type})")
-            log_text["Failure"] = f"HTTPException with code {e.code}."
-            log_content = mod_role.mention
-
-        # Check if the user is currently being watched by Big Brother.
-        try:
-            active_watch = await self.bot.api_client.get(
-                "bot/infractions",
-                params={
-                    "active": "true",
-                    "type": "watch",
-                    "user__id": user_id
-                }
+    # region: Base pardon functions
+
+    async def pardon_mute(self, user_id: int, guild: discord.Guild, reason: str) -> t.Dict[str, str]:
+        """Remove a user's muted role, DM them a notification, and return a log dict."""
+        user = guild.get_member(user_id)
+        log_text = {}
+
+        if user:
+            # Remove the muted role.
+            self.mod_log.ignore(Event.member_update, user.id)
+            await user.remove_roles(self._muted_role, reason=reason)
+
+            # DM the user about the expiration.
+            notified = await utils.notify_pardon(
+                user=user,
+                title="You have been unmuted",
+                content="You may now send messages in the server.",
+                icon_url=utils.INFRACTION_ICONS["mute"][1]
             )
 
-            log_text["Watching"] = "Yes" if active_watch else "No"
-        except ResponseCodeError:
-            log.exception(f"Failed to fetch watch status for user {user_id}")
-            log_text["Watching"] = "Unknown - failed to fetch watch status."
-
-        try:
-            # Mark infraction as inactive in the database.
-            await self.bot.api_client.patch(
-                f"bot/infractions/{_id}",
-                json={"active": False}
-            )
-        except ResponseCodeError as e:
-            log.exception(f"Failed to deactivate infraction #{_id} ({_type})")
-            log_line = f"API request failed with code {e.status}."
-            log_content = mod_role.mention
-
-            # Append to an existing failure message if possible
-            if "Failure" in log_text:
-                log_text["Failure"] += f" {log_line}"
-            else:
-                log_text["Failure"] = log_line
-
-        # Cancel the expiration task.
-        if infraction["expires_at"] is not None:
-            self.cancel_task(infraction["id"])
-
-        # Send a log message to the mod log.
-        if send_log:
-            log_title = f"expiration failed" if "Failure" in log_text else "expired"
-
-            await self.mod_log.send_log_message(
-                icon_url=utils.INFRACTION_ICONS[_type][1],
-                colour=Colours.soft_green,
-                title=f"Infraction {log_title}: {_type}",
-                text="\n".join(f"{k}: {v}" for k, v in log_text.items()),
-                footer=f"ID: {_id}",
-                content=log_content,
-            )
+            log_text["Member"] = f"{user.mention}(`{user.id}`)"
+            log_text["DM"] = "Sent" if notified else "**Failed**"
+        else:
+            log.info(f"Failed to unmute user {user_id}: user not found")
+            log_text["Failure"] = "User was not found in the guild."
 
         return log_text
 
-    async def apply_infraction(
-        self,
-        ctx: Context,
-        infraction: utils.Infraction,
-        user: MemberObject,
-        action_coro: t.Optional[t.Awaitable] = None
-    ) -> None:
-        """Apply an infraction to the user, log the infraction, and optionally notify the user."""
-        infr_type = infraction["type"]
-        icon = utils.INFRACTION_ICONS[infr_type][0]
-        reason = infraction["reason"]
-        expiry = infraction["expires_at"]
-
-        if expiry:
-            expiry = time.format_infraction(expiry)
-
-        # Default values for the confirmation message and mod log.
-        confirm_msg = f":ok_hand: applied"
-        expiry_msg = f" until {expiry}" if expiry else " permanently"
-        dm_result = ""
-        dm_log_text = ""
-        expiry_log_text = f"Expires: {expiry}" if expiry else ""
-        log_title = "applied"
-        log_content = None
-
-        # DM the user about the infraction if it's not a shadow/hidden infraction.
-        if not infraction["hidden"]:
-            # Sometimes user is a discord.Object; make it a proper user.
-            await self.bot.fetch_user(user.id)
-
-            # Accordingly display whether the user was successfully notified via DM.
-            if await utils.notify_infraction(user, infr_type, expiry, reason, icon):
-                dm_result = ":incoming_envelope: "
-                dm_log_text = "\nDM: Sent"
-            else:
-                dm_log_text = "\nDM: **Failed**"
-                log_content = ctx.author.mention
-
-        if infraction["actor"] == self.bot.user.id:
-            end_msg = f" (reason: {infraction['reason']})"
-        else:
-            infractions = await self.bot.api_client.get(
-                "bot/infractions",
-                params={"user__id": str(user.id)}
-            )
-            end_msg = f" ({len(infractions)} infractions total)"
-
-        # Execute the necessary actions to apply the infraction on Discord.
-        if action_coro:
-            try:
-                await action_coro
-                if expiry:
-                    # Schedule the expiration of the infraction.
-                    self.schedule_task(ctx.bot.loop, infraction["id"], infraction)
-            except discord.Forbidden:
-                # Accordingly display that applying the infraction failed.
-                confirm_msg = f":x: failed to apply"
-                expiry_msg = ""
-                log_content = ctx.author.mention
-                log_title = "failed to apply"
-
-        # Send a confirmation message to the invoking context.
-        await ctx.send(
-            f"{dm_result}{confirm_msg} **{infr_type}** to {user.mention}{expiry_msg}{end_msg}."
-        )
+    async def pardon_ban(self, user_id: int, guild: discord.Guild, reason: str) -> t.Dict[str, str]:
+        """Remove a user's ban on the Discord guild and return a log dict."""
+        user = discord.Object(user_id)
+        log_text = {}
 
-        # Send a log message to the mod log.
-        await self.mod_log.send_log_message(
-            icon_url=icon,
-            colour=Colours.soft_red,
-            title=f"Infraction {log_title}: {infr_type}",
-            thumbnail=user.avatar_url_as(static_format="png"),
-            text=textwrap.dedent(f"""
-                Member: {user.mention} (`{user.id}`)
-                Actor: {ctx.message.author}{dm_log_text}
-                Reason: {reason}
-                {expiry_log_text}
-            """),
-            content=log_content,
-            footer=f"ID {infraction['id']}"
-        )
+        self.mod_log.ignore(Event.member_unban, user_id)
 
-    async def pardon_infraction(self, ctx: Context, infr_type: str, user: MemberObject) -> None:
-        """Prematurely end an infraction for a user and log the action in the mod log."""
-        # Check the current active infraction
-        response = await self.bot.api_client.get(
-            'bot/infractions',
-            params={
-                'active': 'true',
-                'type': infr_type,
-                'user__id': user.id
-            }
-        )
+        try:
+            await guild.unban(user, reason=reason)
+        except discord.NotFound:
+            log.info(f"Failed to unban user {user_id}: no active ban found on Discord")
+            log_text["Note"] = "No active ban found on Discord."
 
-        if not response:
-            await ctx.send(f":x: There's no active {infr_type} infraction for user {user.mention}.")
-            return
+        return log_text
 
-        # Deactivate the infraction and cancel its scheduled expiration task.
-        log_text = await self.deactivate_infraction(response[0], send_log=False)
-
-        log_text["Member"] = f"{user.mention}(`{user.id}`)"
-        log_text["Actor"] = str(ctx.message.author)
-        log_content = None
-        footer = f"ID: {response[0]['id']}"
-
-        # If multiple active infractions were found, mark them as inactive in the database
-        # and cancel their expiration tasks.
-        if len(response) > 1:
-            log.warning(f"Found more than one active {infr_type} infraction for user {user.id}")
-
-            footer = f"Infraction IDs: {', '.join(str(infr['id']) for infr in response)}"
-
-            log_note = f"Found multiple **active** {infr_type} infractions in the database."
-            if "Note" in log_text:
-                log_text["Note"] = f" {log_note}"
-            else:
-                log_text["Note"] = log_note
-
-            # deactivate_infraction() is not called again because:
-            #     1. Discord cannot store multiple active bans or assign multiples of the same role
-            #     2. It would send a pardon DM for each active infraction, which is redundant
-            for infraction in response[1:]:
-                _id = infraction['id']
-                try:
-                    # Mark infraction as inactive in the database.
-                    await self.bot.api_client.patch(
-                        f"bot/infractions/{_id}",
-                        json={"active": False}
-                    )
-                except ResponseCodeError:
-                    log.exception(f"Failed to deactivate infraction #{_id} ({infr_type})")
-                    # This is simpler and cleaner than trying to concatenate all the errors.
-                    log_text["Failure"] = "See bot's logs for details."
-
-                # Cancel pending expiration task.
-                if infraction["expires_at"] is not None:
-                    self.cancel_task(infraction["id"])
-
-        # Accordingly display whether the user was successfully notified via DM.
-        dm_emoji = ""
-        if log_text.get("DM") == "Sent":
-            dm_emoji = ":incoming_envelope: "
-        elif "DM" in log_text:
-            # Mention the actor because the DM failed to send.
-            log_content = ctx.author.mention
-
-        # Accordingly display whether the pardon failed.
-        if "Failure" in log_text:
-            confirm_msg = ":x: failed to pardon"
-            log_title = "pardon failed"
-            log_content = ctx.author.mention
-        else:
-            confirm_msg = f":ok_hand: pardoned"
-            log_title = "pardoned"
+    async def _pardon_action(self, infraction: utils.Infraction) -> t.Optional[t.Dict[str, str]]:
+        """
+        Execute deactivation steps specific to the infraction's type and return a log dict.
 
-        # Send a confirmation message to the invoking context.
-        await ctx.send(
-            f"{dm_emoji}{confirm_msg} infraction **{infr_type}** for {user.mention}. "
-            f"{log_text.get('Failure', '')}"
-        )
+        If an infraction type is unsupported, return None instead.
+        """
+        guild = self.bot.get_guild(constants.Guild.id)
+        user_id = infraction["user"]
+        reason = f"Infraction #{infraction['id']} expired or was pardoned."
 
-        # Send a log message to the mod log.
-        await self.mod_log.send_log_message(
-            icon_url=utils.INFRACTION_ICONS[infr_type][1],
-            colour=Colours.soft_green,
-            title=f"Infraction {log_title}: {infr_type}",
-            thumbnail=user.avatar_url_as(static_format="png"),
-            text="\n".join(f"{k}: {v}" for k, v in log_text.items()),
-            footer=footer,
-            content=log_content,
-        )
+        if infraction["type"] == "mute":
+            return await self.pardon_mute(user_id, guild, reason)
+        elif infraction["type"] == "ban":
+            return await self.pardon_ban(user_id, guild, reason)
 
     # endregion
 
diff --git a/bot/cogs/moderation/management.py b/bot/cogs/moderation/management.py
index 491f6d400..0636422d3 100644
--- a/bot/cogs/moderation/management.py
+++ b/bot/cogs/moderation/management.py
@@ -2,40 +2,31 @@ import asyncio
 import logging
 import textwrap
 import typing as t
+from datetime import datetime
 
 import discord
 from discord.ext import commands
 from discord.ext.commands import Context
 
 from bot import constants
-from bot.converters import InfractionSearchQuery
+from bot.bot import Bot
+from bot.converters import Expiry, InfractionSearchQuery, allowed_strings, proxy_user
 from bot.pagination import LinePaginator
 from bot.utils import time
-from bot.utils.checks import with_role_check
+from bot.utils.checks import in_channel_check, with_role_check
 from . import utils
 from .infractions import Infractions
 from .modlog import ModLog
 
 log = logging.getLogger(__name__)
 
-UserConverter = t.Union[discord.User, utils.proxy_user]
-
-
-def permanent_duration(expires_at: str) -> str:
-    """Only allow an expiration to be 'permanent' if it is a string."""
-    expires_at = expires_at.lower()
-    if expires_at != "permanent":
-        raise commands.BadArgument
-    else:
-        return expires_at
-
 
 class ModManagement(commands.Cog):
     """Management of infractions."""
 
     category = "Moderation"
 
-    def __init__(self, bot: commands.Bot):
+    def __init__(self, bot: Bot):
         self.bot = bot
 
     @property
@@ -59,8 +50,8 @@ class ModManagement(commands.Cog):
     async def infraction_edit(
         self,
         ctx: Context,
-        infraction_id: int,
-        duration: t.Union[utils.Expiry, permanent_duration, None],
+        infraction_id: t.Union[int, allowed_strings("l", "last", "recent")],
+        duration: t.Union[Expiry, allowed_strings("p", "permanent"), None],
         *,
         reason: str = None
     ) -> None:
@@ -77,26 +68,45 @@ class ModManagement(commands.Cog):
         \u2003`M` - minutes∗
         \u2003`s` - seconds
 
-        Use "permanent" to mark the infraction as permanent. Alternatively, an ISO 8601 timestamp
-        can be provided for the duration.
+        Use "l", "last", or "recent" as the infraction ID to specify that the most recent infraction
+        authored by the command invoker should be edited.
+
+        Use "p" or "permanent" to mark the infraction as permanent. Alternatively, an ISO 8601
+        timestamp can be provided for the duration.
         """
         if duration is None and reason is None:
             # Unlike UserInputError, the error handler will show a specified message for BadArgument
             raise commands.BadArgument("Neither a new expiry nor a new reason was specified.")
 
         # Retrieve the previous infraction for its information.
-        old_infraction = await self.bot.api_client.get(f'bot/infractions/{infraction_id}')
+        if isinstance(infraction_id, str):
+            params = {
+                "actor__id": ctx.author.id,
+                "ordering": "-inserted_at"
+            }
+            infractions = await self.bot.api_client.get(f"bot/infractions", params=params)
+
+            if infractions:
+                old_infraction = infractions[0]
+                infraction_id = old_infraction["id"]
+            else:
+                await ctx.send(
+                    f":x: Couldn't find most recent infraction; you have never given an infraction."
+                )
+                return
+        else:
+            old_infraction = await self.bot.api_client.get(f"bot/infractions/{infraction_id}")
 
         request_data = {}
         confirm_messages = []
         log_text = ""
 
-        if duration == "permanent":
+        if isinstance(duration, str):
             request_data['expires_at'] = None
             confirm_messages.append("marked as permanent")
         elif duration is not None:
             request_data['expires_at'] = duration.isoformat()
-            expiry = duration.strftime(time.INFRACTION_FORMAT)
+            expiry = time.format_infraction_with_duration(request_data['expires_at'])
             confirm_messages.append(f"set to expire on {expiry}")
         else:
             confirm_messages.append("expiry unchanged")
@@ -128,7 +138,8 @@ class ModManagement(commands.Cog):
                 New expiry: {new_infraction['expires_at'] or "Permanent"}
             """.rstrip()
 
-        await ctx.send(f":ok_hand: Updated infraction: {' & '.join(confirm_messages)}")
+        changes = ' & '.join(confirm_messages)
+        await ctx.send(f":ok_hand: Updated infraction #{infraction_id}: {changes}")
 
         # Get information about the infraction's user
         user_id = new_infraction['user']
@@ -169,7 +180,7 @@ class ModManagement(commands.Cog):
             await ctx.invoke(self.search_reason, query)
 
     @infraction_search_group.command(name="user", aliases=("member", "id"))
-    async def search_user(self, ctx: Context, user: UserConverter) -> None:
+    async def search_user(self, ctx: Context, user: t.Union[discord.User, proxy_user]) -> None:
         """Search for infractions by member."""
         infraction_list = await self.bot.api_client.get(
             'bot/infractions',
@@ -231,10 +242,17 @@ class ModManagement(commands.Cog):
         user_id = infraction["user"]
         hidden = infraction["hidden"]
         created = time.format_infraction(infraction["inserted_at"])
+
+        if active:
+            remaining = time.until_expiration(infraction["expires_at"]) or "Expired"
+        else:
+            remaining = "Inactive"
+
         if infraction["expires_at"] is None:
             expires = "*Permanent*"
         else:
-            expires = time.format_infraction(infraction["expires_at"])
+            date_from = datetime.strptime(created, time.INFRACTION_FORMAT)
+            expires = time.format_infraction_with_duration(infraction["expires_at"], date_from)
 
         lines = textwrap.dedent(f"""
             {"**===============**" if active else "==============="}
@@ -245,6 +263,7 @@ class ModManagement(commands.Cog):
             Reason: {infraction["reason"] or "*None*"}
             Created: {created}
             Expires: {expires}
+            Remaining: {remaining}
             Actor: {actor.mention if actor else actor_id}
             ID: `{infraction["id"]}`
             {"**===============**" if active else "==============="}
@@ -256,8 +275,12 @@ class ModManagement(commands.Cog):
 
     # This cannot be static (must have a __func__ attribute).
     def cog_check(self, ctx: Context) -> bool:
-        """Only allow moderators to invoke the commands in this cog."""
-        return with_role_check(ctx, *constants.MODERATION_ROLES)
+        """Only allow moderators from moderator channels to invoke the commands in this cog."""
+        checks = [
+            with_role_check(ctx, *constants.MODERATION_ROLES),
+            in_channel_check(ctx, *constants.MODERATION_CHANNELS)
+        ]
+        return all(checks)
 
     # This cannot be static (must have a __func__ attribute).
     async def cog_command_error(self, ctx: Context, error: Exception) -> None:
diff --git a/bot/cogs/moderation/modlog.py b/bot/cogs/moderation/modlog.py
index 118503517..e8ae0dbe6 100644
--- a/bot/cogs/moderation/modlog.py
+++ b/bot/cogs/moderation/modlog.py
@@ -1,18 +1,21 @@
 import asyncio
+import difflib
+import itertools
 import logging
 import typing as t
 from datetime import datetime
+from itertools import zip_longest
 
 import discord
 from dateutil.relativedelta import relativedelta
 from deepdiff import DeepDiff
 from discord import Colour
 from discord.abc import GuildChannel
-from discord.ext.commands import Bot, Cog, Context
+from discord.ext.commands import Cog, Context
 
+from bot.bot import Bot
 from bot.constants import Channels, Colours, Emojis, Event, Guild as GuildConstant, Icons, URLs
 from bot.utils.time import humanize_delta
-from .utils import UserTypes
 
 log = logging.getLogger(__name__)
 
@@ -23,6 +26,12 @@ CHANNEL_CHANGES_SUPPRESSED = ("_overwrites", "position")
 MEMBER_CHANGES_SUPPRESSED = ("status", "activities", "_client_status", "nick")
 ROLE_CHANGES_UNSUPPORTED = ("colour", "permissions")
 
+VOICE_STATE_ATTRIBUTES = {
+    "channel.name": "Channel",
+    "self_stream": "Streaming",
+    "self_video": "Broadcasting",
+}
+
 
 class ModLog(Cog, name="ModLog"):
     """Logging for server events and staff actions."""
@@ -34,14 +43,16 @@ class ModLog(Cog, name="ModLog"):
         self._cached_deletes = []
         self._cached_edits = []
 
-    async def upload_log(self, messages: t.List[discord.Message], actor_id: int) -> str:
-        """
-        Uploads the log data to the database via an API endpoint for uploading logs.
-
-        Used in several mod log embeds.
+    async def upload_log(
+        self,
+        messages: t.Iterable[discord.Message],
+        actor_id: int,
+        attachments: t.Iterable[t.List[str]] = None
+    ) -> str:
+        """Upload message logs to the database and return a URL to a page for viewing the logs."""
+        if attachments is None:
+            attachments = []
 
-        Returns a URL that can be used to view the log.
-        """
         response = await self.bot.api_client.post(
             'bot/deleted-messages',
             json={
@@ -53,9 +64,10 @@ class ModLog(Cog, name="ModLog"):
                         'author': message.author.id,
                         'channel_id': message.channel.id,
                         'content': message.content,
-                        'embeds': [embed.to_dict() for embed in message.embeds]
+                        'embeds': [embed.to_dict() for embed in message.embeds],
+                        'attachments': attachment,
                     }
-                    for message in messages
+                    for message, attachment in zip_longest(messages, attachments)
                 ]
             }
         )
@@ -203,7 +215,7 @@ class ModLog(Cog, name="ModLog"):
                 new = value["new_value"]
                 old = value["old_value"]
 
-                changes.append(f"**{key.title()}:** `{old}` **->** `{new}`")
+                changes.append(f"**{key.title()}:** `{old}` **→** `{new}`")
 
             done.append(key)
 
@@ -281,7 +293,7 @@ class ModLog(Cog, name="ModLog"):
                 new = value["new_value"]
                 old = value["old_value"]
 
-                changes.append(f"**{key.title()}:** `{old}` **->** `{new}`")
+                changes.append(f"**{key.title()}:** `{old}` **→** `{new}`")
 
             done.append(key)
 
@@ -331,7 +343,7 @@ class ModLog(Cog, name="ModLog"):
             new = value["new_value"]
             old = value["old_value"]
 
-            changes.append(f"**{key.title()}:** `{old}` **->** `{new}`")
+            changes.append(f"**{key.title()}:** `{old}` **→** `{new}`")
 
             done.append(key)
 
@@ -352,7 +364,7 @@ class ModLog(Cog, name="ModLog"):
         )
 
     @Cog.listener()
-    async def on_member_ban(self, guild: discord.Guild, member: UserTypes) -> None:
+    async def on_member_ban(self, guild: discord.Guild, member: discord.Member) -> None:
         """Log ban event to user log."""
         if guild.id != GuildConstant.id:
             return
@@ -363,7 +375,7 @@ class ModLog(Cog, name="ModLog"):
 
         await self.send_log_message(
             Icons.user_ban, Colours.soft_red,
-            "User banned", f"{member.name}#{member.discriminator} (`{member.id}`)",
+            "User banned", f"{member} (`{member.id}`)",
             thumbnail=member.avatar_url_as(static_format="png"),
             channel_id=Channels.userlog
         )
@@ -374,7 +386,7 @@ class ModLog(Cog, name="ModLog"):
         if member.guild.id != GuildConstant.id:
             return
 
-        message = f"{member.name}#{member.discriminator} (`{member.id}`)"
+        message = f"{member} (`{member.id}`)"
         now = datetime.utcnow()
         difference = abs(relativedelta(now, member.created_at))
 
@@ -402,7 +414,7 @@ class ModLog(Cog, name="ModLog"):
 
         await self.send_log_message(
             Icons.sign_out, Colours.soft_red,
-            "User left", f"{member.name}#{member.discriminator} (`{member.id}`)",
+            "User left", f"{member} (`{member.id}`)",
             thumbnail=member.avatar_url_as(static_format="png"),
             channel_id=Channels.userlog
         )
@@ -419,7 +431,7 @@ class ModLog(Cog, name="ModLog"):
 
         await self.send_log_message(
             Icons.user_unban, Colour.blurple(),
-            "User unbanned", f"{member.name}#{member.discriminator} (`{member.id}`)",
+            "User unbanned", f"{member} (`{member.id}`)",
             thumbnail=member.avatar_url_as(static_format="png"),
             channel_id=Channels.modlog
         )
@@ -484,23 +496,23 @@ class ModLog(Cog, name="ModLog"):
                 old = value.get("old_value")
 
                 if new and old:
-                    changes.append(f"**{key.title()}:** `{old}` **->** `{new}`")
+                    changes.append(f"**{key.title()}:** `{old}` **→** `{new}`")
 
             done.append(key)
 
         if before.name != after.name:
             changes.append(
-                f"**Username:** `{before.name}` **->** `{after.name}`"
+                f"**Username:** `{before.name}` **→** `{after.name}`"
             )
 
         if before.discriminator != after.discriminator:
             changes.append(
-                f"**Discriminator:** `{before.discriminator}` **->** `{after.discriminator}`"
+                f"**Discriminator:** `{before.discriminator}` **→** `{after.discriminator}`"
             )
 
         if before.display_name != after.display_name:
             changes.append(
-                f"**Display name:** `{before.display_name}` **->** `{after.display_name}`"
+                f"**Display name:** `{before.display_name}` **→** `{after.display_name}`"
             )
 
         if not changes:
@@ -511,7 +523,7 @@ class ModLog(Cog, name="ModLog"):
         for item in sorted(changes):
             message += f"{Emojis.bullet} {item}\n"
 
-        message = f"**{after.name}#{after.discriminator}** (`{after.id}`)\n{message}"
+        message = f"**{after}** (`{after.id}`)\n{message}"
 
         await self.send_log_message(
             Icons.user_update, Colour.blurple(),
@@ -540,14 +552,14 @@ class ModLog(Cog, name="ModLog"):
 
         if channel.category:
             response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
+                f"**Author:** {author} (`{author.id}`)\n"
                 f"**Channel:** {channel.category}/#{channel.name} (`{channel.id}`)\n"
                 f"**Message ID:** `{message.id}`\n"
                 "\n"
             )
         else:
             response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
+                f"**Author:** {author} (`{author.id}`)\n"
                 f"**Channel:** #{channel.name} (`{channel.id}`)\n"
                 f"**Message ID:** `{message.id}`\n"
                 "\n"
@@ -618,80 +630,81 @@ class ModLog(Cog, name="ModLog"):
         )
 
     @Cog.listener()
-    async def on_message_edit(self, before: discord.Message, after: discord.Message) -> None:
+    async def on_message_edit(self, msg_before: discord.Message, msg_after: discord.Message) -> None:
         """Log message edit event to message change log."""
         if (
-            not before.guild
-            or before.guild.id != GuildConstant.id
-            or before.channel.id in GuildConstant.ignored
-            or before.author.bot
+            not msg_before.guild
+            or msg_before.guild.id != GuildConstant.id
+            or msg_before.channel.id in GuildConstant.ignored
+            or msg_before.author.bot
         ):
             return
 
-        self._cached_edits.append(before.id)
+        self._cached_edits.append(msg_before.id)
 
-        if before.content == after.content:
+        if msg_before.content == msg_after.content:
             return
 
-        author = before.author
-        channel = before.channel
-
-        if channel.category:
-            before_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** {channel.category}/#{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{before.id}`\n"
-                "\n"
-                f"{before.clean_content}"
-            )
+        author = msg_before.author
+        channel = msg_before.channel
+        channel_name = f"{channel.category}/#{channel.name}" if channel.category else f"#{channel.name}"
 
-            after_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** {channel.category}/#{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{before.id}`\n"
-                "\n"
-                f"{after.clean_content}"
-            )
-        else:
-            before_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** #{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{before.id}`\n"
-                "\n"
-                f"{before.clean_content}"
-            )
+        # Getting the difference per words and group them by type - add, remove, same
+        # Note that this is intended grouping without sorting
+        diff = difflib.ndiff(msg_before.clean_content.split(), msg_after.clean_content.split())
+        diff_groups = tuple(
+            (diff_type, tuple(s[2:] for s in diff_words))
+            for diff_type, diff_words in itertools.groupby(diff, key=lambda s: s[0])
+        )
 
-            after_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** #{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{before.id}`\n"
-                "\n"
-                f"{after.clean_content}"
-            )
+        content_before: t.List[str] = []
+        content_after: t.List[str] = []
+
+        for index, (diff_type, words) in enumerate(diff_groups):
+            sub = ' '.join(words)
+            if diff_type == '-':
+                content_before.append(f"[{sub}](http://o.hi)")
+            elif diff_type == '+':
+                content_after.append(f"[{sub}](http://o.hi)")
+            elif diff_type == ' ':
+                if len(words) > 2:
+                    sub = (
+                        f"{words[0] if index > 0 else ''}"
+                        " ... "
+                        f"{words[-1] if index < len(diff_groups) - 1 else ''}"
+                    )
+                content_before.append(sub)
+                content_after.append(sub)
+
+        response = (
+            f"**Author:** {author} (`{author.id}`)\n"
+            f"**Channel:** {channel_name} (`{channel.id}`)\n"
+            f"**Message ID:** `{msg_before.id}`\n"
+            "\n"
+            f"**Before**:\n{' '.join(content_before)}\n"
+            f"**After**:\n{' '.join(content_after)}\n"
+            "\n"
+            f"[Jump to message]({msg_after.jump_url})"
+        )
 
-        if before.edited_at:
+        if msg_before.edited_at:
             # Message was previously edited, to assist with self-bot detection, use the edited_at
             # datetime as the baseline and create a human-readable delta between this edit event
             # and the last time the message was edited
-            timestamp = before.edited_at
-            delta = humanize_delta(relativedelta(after.edited_at, before.edited_at))
+            timestamp = msg_before.edited_at
+            delta = humanize_delta(relativedelta(msg_after.edited_at, msg_before.edited_at))
             footer = f"Last edited {delta} ago"
         else:
             # Message was not previously edited, use the created_at datetime as the baseline, no
             # delta calculation needed
-            timestamp = before.created_at
+            timestamp = msg_before.created_at
             footer = None
 
         await self.send_log_message(
-            Icons.message_edit, Colour.blurple(), "Message edited (Before)", before_response,
+            Icons.message_edit, Colour.blurple(), "Message edited", response,
             channel_id=Channels.message_log, timestamp_override=timestamp, footer=footer
         )
 
-        await self.send_log_message(
-            Icons.message_edit, Colour.blurple(), "Message edited (After)", after_response,
-            channel_id=Channels.message_log, timestamp_override=after.edited_at
-        )
-
     @Cog.listener()
     async def on_raw_message_edit(self, event: discord.RawMessageUpdateEvent) -> None:
         """Log raw message edit event to message change log."""
@@ -718,39 +731,23 @@ class ModLog(Cog, name="ModLog"):
 
         author = message.author
         channel = message.channel
+        channel_name = f"{channel.category}/#{channel.name}" if channel.category else f"#{channel.name}"
+
+        before_response = (
+            f"**Author:** {author} (`{author.id}`)\n"
+            f"**Channel:** {channel_name} (`{channel.id}`)\n"
+            f"**Message ID:** `{message.id}`\n"
+            "\n"
+            "This message was not cached, so the message content cannot be displayed."
+        )
 
-        if channel.category:
-            before_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** {channel.category}/#{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{message.id}`\n"
-                "\n"
-                "This message was not cached, so the message content cannot be displayed."
-            )
-
-            after_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** {channel.category}/#{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{message.id}`\n"
-                "\n"
-                f"{message.clean_content}"
-            )
-        else:
-            before_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** #{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{message.id}`\n"
-                "\n"
-                "This message was not cached, so the message content cannot be displayed."
-            )
-
-            after_response = (
-                f"**Author:** {author.name}#{author.discriminator} (`{author.id}`)\n"
-                f"**Channel:** #{channel.name} (`{channel.id}`)\n"
-                f"**Message ID:** `{message.id}`\n"
-                "\n"
-                f"{message.clean_content}"
-            )
+        after_response = (
+            f"**Author:** {author} (`{author.id}`)\n"
+            f"**Channel:** {channel_name} (`{channel.id}`)\n"
+            f"**Message ID:** `{message.id}`\n"
+            "\n"
+            f"{message.clean_content}"
+        )
 
         await self.send_log_message(
             Icons.message_edit, Colour.blurple(), "Message edited (Before)",
@@ -761,3 +758,76 @@ class ModLog(Cog, name="ModLog"):
             Icons.message_edit, Colour.blurple(), "Message edited (After)",
             after_response, channel_id=Channels.message_log
         )
+
+    @Cog.listener()
+    async def on_voice_state_update(
+        self,
+        member: discord.Member,
+        before: discord.VoiceState,
+        after: discord.VoiceState
+    ) -> None:
+        """Log member voice state changes to the voice log channel."""
+        if (
+            member.guild.id != GuildConstant.id
+            or (before.channel and before.channel.id in GuildConstant.ignored)
+        ):
+            return
+
+        if member.id in self._ignored[Event.voice_state_update]:
+            self._ignored[Event.voice_state_update].remove(member.id)
+            return
+
+        # Exclude all channel attributes except the name.
+        diff = DeepDiff(
+            before,
+            after,
+            exclude_paths=("root.session_id", "root.afk"),
+            exclude_regex_paths=r"root\.channel\.(?!name)",
+        )
+
+        # A type change seems to always take precedent over a value change. Furthermore, it will
+        # include the value change along with the type change anyway. Therefore, it's OK to
+        # "overwrite" values_changed; in practice there will never even be anything to overwrite.
+        diff_values = {**diff.get("values_changed", {}), **diff.get("type_changes", {})}
+
+        icon = Icons.voice_state_blue
+        colour = Colour.blurple()
+        changes = []
+
+        for attr, values in diff_values.items():
+            if not attr:  # Not sure why, but it happens.
+                continue
+
+            old = values["old_value"]
+            new = values["new_value"]
+
+            attr = attr[5:]  # Remove "root." prefix.
+            attr = VOICE_STATE_ATTRIBUTES.get(attr, attr.replace("_", " ").capitalize())
+
+            changes.append(f"**{attr}:** `{old}` **→** `{new}`")
+
+            # Set the embed icon and colour depending on which attribute changed.
+            if any(name in attr for name in ("Channel", "deaf", "mute")):
+                if new is None or new is True:
+                    # Left a channel or was muted/deafened.
+                    icon = Icons.voice_state_red
+                    colour = Colours.soft_red
+                elif old is None or old is True:
+                    # Joined a channel or was unmuted/undeafened.
+                    icon = Icons.voice_state_green
+                    colour = Colours.soft_green
+
+        if not changes:
+            return
+
+        message = "\n".join(f"{Emojis.bullet} {item}" for item in sorted(changes))
+        message = f"**{member}** (`{member.id}`)\n{message}"
+
+        await self.send_log_message(
+            icon_url=icon,
+            colour=colour,
+            title="Voice state updated",
+            text=message,
+            thumbnail=member.avatar_url_as(static_format="png"),
+            channel_id=Channels.voice_log
+        )
diff --git a/bot/cogs/moderation/scheduler.py b/bot/cogs/moderation/scheduler.py
new file mode 100644
index 000000000..e14c302cb
--- /dev/null
+++ b/bot/cogs/moderation/scheduler.py
@@ -0,0 +1,418 @@
+import logging
+import textwrap
+import typing as t
+from abc import abstractmethod
+from datetime import datetime
+from gettext import ngettext
+
+import dateutil.parser
+import discord
+from discord.ext.commands import Context
+
+from bot import constants
+from bot.api import ResponseCodeError
+from bot.bot import Bot
+from bot.constants import Colours, STAFF_CHANNELS
+from bot.utils import time
+from bot.utils.scheduling import Scheduler
+from . import utils
+from .modlog import ModLog
+from .utils import UserSnowflake
+
+log = logging.getLogger(__name__)
+
+
+class InfractionScheduler(Scheduler):
+    """Handles the application, pardoning, and expiration of infractions."""
+
+    def __init__(self, bot: Bot, supported_infractions: t.Container[str]):
+        super().__init__()
+
+        self.bot = bot
+        self.bot.loop.create_task(self.reschedule_infractions(supported_infractions))
+
+    @property
+    def mod_log(self) -> ModLog:
+        """Get the currently loaded ModLog cog instance."""
+        return self.bot.get_cog("ModLog")
+
+    async def reschedule_infractions(self, supported_infractions: t.Container[str]) -> None:
+        """Schedule expiration for previous infractions."""
+        await self.bot.wait_until_ready()
+
+        log.trace(f"Rescheduling infractions for {self.__class__.__name__}.")
+
+        infractions = await self.bot.api_client.get(
+            'bot/infractions',
+            params={'active': 'true'}
+        )
+        for infraction in infractions:
+            if infraction["expires_at"] is not None and infraction["type"] in supported_infractions:
+                self.schedule_task(self.bot.loop, infraction["id"], infraction)
+
+    async def reapply_infraction(
+        self,
+        infraction: utils.Infraction,
+        apply_coro: t.Optional[t.Awaitable]
+    ) -> None:
+        """Reapply an infraction if it's still active or deactivate it if less than 60 sec left."""
+        # Calculate the time remaining, in seconds, for the mute.
+        expiry = dateutil.parser.isoparse(infraction["expires_at"]).replace(tzinfo=None)
+        delta = (expiry - datetime.utcnow()).total_seconds()
+
+        # Mark as inactive if less than a minute remains.
+        if delta < 60:
+            log.info(
+                "Infraction will be deactivated instead of re-applied "
+                "because less than 1 minute remains."
+            )
+            await self.deactivate_infraction(infraction)
+            return
+
+        # Allowing mod log since this is a passive action that should be logged.
+        await apply_coro
+        log.info(f"Re-applied {infraction['type']} to user {infraction['user']} upon rejoining.")
+
+    async def apply_infraction(
+        self,
+        ctx: Context,
+        infraction: utils.Infraction,
+        user: UserSnowflake,
+        action_coro: t.Optional[t.Awaitable] = None
+    ) -> None:
+        """Apply an infraction to the user, log the infraction, and optionally notify the user."""
+        infr_type = infraction["type"]
+        icon = utils.INFRACTION_ICONS[infr_type][0]
+        reason = infraction["reason"]
+        expiry = time.format_infraction_with_duration(infraction["expires_at"])
+        id_ = infraction['id']
+
+        log.trace(f"Applying {infr_type} infraction #{id_} to {user}.")
+
+        # Default values for the confirmation message and mod log.
+        confirm_msg = f":ok_hand: applied"
+
+        # Specifying an expiry for a note or warning makes no sense.
+        if infr_type in ("note", "warning"):
+            expiry_msg = ""
+        else:
+            expiry_msg = f" until {expiry}" if expiry else " permanently"
+
+        dm_result = ""
+        dm_log_text = ""
+        expiry_log_text = f"Expires: {expiry}" if expiry else ""
+        log_title = "applied"
+        log_content = None
+
+        # DM the user about the infraction if it's not a shadow/hidden infraction.
+        if not infraction["hidden"]:
+            dm_result = f"{constants.Emojis.failmail} "
+            dm_log_text = "\nDM: **Failed**"
+
+            # Sometimes user is a discord.Object; make it a proper user.
+            try:
+                if not isinstance(user, (discord.Member, discord.User)):
+                    user = await self.bot.fetch_user(user.id)
+            except discord.HTTPException as e:
+                log.error(f"Failed to DM {user.id}: could not fetch user (status {e.status})")
+            else:
+                # Accordingly display whether the user was successfully notified via DM.
+                if await utils.notify_infraction(user, infr_type, expiry, reason, icon):
+                    dm_result = ":incoming_envelope: "
+                    dm_log_text = "\nDM: Sent"
+
+        if infraction["actor"] == self.bot.user.id:
+            log.trace(
+                f"Infraction #{id_} actor is bot; including the reason in the confirmation message."
+            )
+
+            end_msg = f" (reason: {infraction['reason']})"
+        elif ctx.channel.id not in STAFF_CHANNELS:
+            log.trace(
+                f"Infraction #{id_} context is not in a staff channel; omitting infraction count."
+            )
+
+            end_msg = ""
+        else:
+            log.trace(f"Fetching total infraction count for {user}.")
+
+            infractions = await self.bot.api_client.get(
+                "bot/infractions",
+                params={"user__id": str(user.id)}
+            )
+            total = len(infractions)
+            end_msg = f" ({total} infraction{ngettext('', 's', total)} total)"
+
+        # Execute the necessary actions to apply the infraction on Discord.
+        if action_coro:
+            log.trace(f"Awaiting the infraction #{id_} application action coroutine.")
+            try:
+                await action_coro
+                if expiry:
+                    # Schedule the expiration of the infraction.
+                    self.schedule_task(ctx.bot.loop, infraction["id"], infraction)
+            except discord.HTTPException as e:
+                # Accordingly display that applying the infraction failed.
+                confirm_msg = f":x: failed to apply"
+                expiry_msg = ""
+                log_content = ctx.author.mention
+                log_title = "failed to apply"
+
+                log_msg = f"Failed to apply {infr_type} infraction #{id_} to {user}"
+                if isinstance(e, discord.Forbidden):
+                    log.warning(f"{log_msg}: bot lacks permissions.")
+                else:
+                    log.exception(log_msg)
+
+        # Send a confirmation message to the invoking context.
+        log.trace(f"Sending infraction #{id_} confirmation message.")
+        await ctx.send(
+            f"{dm_result}{confirm_msg} **{infr_type}** to {user.mention}{expiry_msg}{end_msg}."
+        )
+
+        # Send a log message to the mod log.
+        log.trace(f"Sending apply mod log for infraction #{id_}.")
+        await self.mod_log.send_log_message(
+            icon_url=icon,
+            colour=Colours.soft_red,
+            title=f"Infraction {log_title}: {infr_type}",
+            thumbnail=user.avatar_url_as(static_format="png"),
+            text=textwrap.dedent(f"""
+                Member: {user.mention} (`{user.id}`)
+                Actor: {ctx.message.author}{dm_log_text}
+                Reason: {reason}
+                {expiry_log_text}
+            """),
+            content=log_content,
+            footer=f"ID {infraction['id']}"
+        )
+
+        log.info(f"Applied {infr_type} infraction #{id_} to {user}.")
+
+    async def pardon_infraction(self, ctx: Context, infr_type: str, user: UserSnowflake) -> None:
+        """Prematurely end an infraction for a user and log the action in the mod log."""
+        log.trace(f"Pardoning {infr_type} infraction for {user}.")
+
+        # Check the current active infraction
+        log.trace(f"Fetching active {infr_type} infractions for {user}.")
+        response = await self.bot.api_client.get(
+            'bot/infractions',
+            params={
+                'active': 'true',
+                'type': infr_type,
+                'user__id': user.id
+            }
+        )
+
+        if not response:
+            log.debug(f"No active {infr_type} infraction found for {user}.")
+            await ctx.send(f":x: There's no active {infr_type} infraction for user {user.mention}.")
+            return
+
+        # Deactivate the infraction and cancel its scheduled expiration task.
+        log_text = await self.deactivate_infraction(response[0], send_log=False)
+
+        log_text["Member"] = f"{user.mention}(`{user.id}`)"
+        log_text["Actor"] = str(ctx.message.author)
+        log_content = None
+        id_ = response[0]['id']
+        footer = f"ID: {id_}"
+
+        # If multiple active infractions were found, mark them as inactive in the database
+        # and cancel their expiration tasks.
+        if len(response) > 1:
+            log.warning(
+                f"Found more than one active {infr_type} infraction for user {user.id}; "
+                "deactivating the extra active infractions too."
+            )
+
+            footer = f"Infraction IDs: {', '.join(str(infr['id']) for infr in response)}"
+
+            log_note = f"Found multiple **active** {infr_type} infractions in the database."
+            if "Note" in log_text:
+                log_text["Note"] = f" {log_note}"
+            else:
+                log_text["Note"] = log_note
+
+            # deactivate_infraction() is not called again because:
+            #     1. Discord cannot store multiple active bans or assign multiples of the same role
+            #     2. It would send a pardon DM for each active infraction, which is redundant
+            for infraction in response[1:]:
+                id_ = infraction['id']
+                try:
+                    # Mark infraction as inactive in the database.
+                    await self.bot.api_client.patch(
+                        f"bot/infractions/{id_}",
+                        json={"active": False}
+                    )
+                except ResponseCodeError:
+                    log.exception(f"Failed to deactivate infraction #{id_} ({infr_type})")
+                    # This is simpler and cleaner than trying to concatenate all the errors.
+                    log_text["Failure"] = "See bot's logs for details."
+
+                # Cancel pending expiration task.
+                if infraction["expires_at"] is not None:
+                    self.cancel_task(infraction["id"])
+
+        # Accordingly display whether the user was successfully notified via DM.
+        dm_emoji = ""
+        if log_text.get("DM") == "Sent":
+            dm_emoji = ":incoming_envelope: "
+        elif "DM" in log_text:
+            dm_emoji = f"{constants.Emojis.failmail} "
+
+        # Accordingly display whether the pardon failed.
+        if "Failure" in log_text:
+            confirm_msg = ":x: failed to pardon"
+            log_title = "pardon failed"
+            log_content = ctx.author.mention
+
+            log.warning(f"Failed to pardon {infr_type} infraction #{id_} for {user}.")
+        else:
+            confirm_msg = f":ok_hand: pardoned"
+            log_title = "pardoned"
+
+            log.info(f"Pardoned {infr_type} infraction #{id_} for {user}.")
+
+        # Send a confirmation message to the invoking context.
+        log.trace(f"Sending infraction #{id_} pardon confirmation message.")
+        await ctx.send(
+            f"{dm_emoji}{confirm_msg} infraction **{infr_type}** for {user.mention}. "
+            f"{log_text.get('Failure', '')}"
+        )
+
+        # Send a log message to the mod log.
+        await self.mod_log.send_log_message(
+            icon_url=utils.INFRACTION_ICONS[infr_type][1],
+            colour=Colours.soft_green,
+            title=f"Infraction {log_title}: {infr_type}",
+            thumbnail=user.avatar_url_as(static_format="png"),
+            text="\n".join(f"{k}: {v}" for k, v in log_text.items()),
+            footer=footer,
+            content=log_content,
+        )
+
+    async def deactivate_infraction(
+        self,
+        infraction: utils.Infraction,
+        send_log: bool = True
+    ) -> t.Dict[str, str]:
+        """
+        Deactivate an active infraction and return a dictionary of lines to send in a mod log.
+
+        The infraction is removed from Discord, marked as inactive in the database, and has its
+        expiration task cancelled. If `send_log` is True, a mod log is sent for the
+        deactivation of the infraction.
+
+        Infractions of unsupported types will raise a ValueError.
+        """
+        guild = self.bot.get_guild(constants.Guild.id)
+        mod_role = guild.get_role(constants.Roles.moderator)
+        user_id = infraction["user"]
+        type_ = infraction["type"]
+        id_ = infraction["id"]
+
+        log.info(f"Marking infraction #{id_} as inactive (expired).")
+
+        log_content = None
+        log_text = {
+            "Member": str(user_id),
+            "Actor": str(self.bot.user),
+            "Reason": infraction["reason"]
+        }
+
+        try:
+            log.trace("Awaiting the pardon action coroutine.")
+            returned_log = await self._pardon_action(infraction)
+
+            if returned_log is not None:
+                log_text = {**log_text, **returned_log}  # Merge the logs together
+            else:
+                raise ValueError(
+                    f"Attempted to deactivate an unsupported infraction #{id_} ({type_})!"
+                )
+        except discord.Forbidden:
+            log.warning(f"Failed to deactivate infraction #{id_} ({type_}): bot lacks permissions.")
+            log_text["Failure"] = f"The bot lacks permissions to do this (role hierarchy?)"
+            log_content = mod_role.mention
+        except discord.HTTPException as e:
+            log.exception(f"Failed to deactivate infraction #{id_} ({type_})")
+            log_text["Failure"] = f"HTTPException with status {e.status} and code {e.code}."
+            log_content = mod_role.mention
+
+        # Check if the user is currently being watched by Big Brother.
+        try:
+            log.trace(f"Determining if user {user_id} is currently being watched by Big Brother.")
+
+            active_watch = await self.bot.api_client.get(
+                "bot/infractions",
+                params={
+                    "active": "true",
+                    "type": "watch",
+                    "user__id": user_id
+                }
+            )
+
+            log_text["Watching"] = "Yes" if active_watch else "No"
+        except ResponseCodeError:
+            log.exception(f"Failed to fetch watch status for user {user_id}")
+            log_text["Watching"] = "Unknown - failed to fetch watch status."
+
+        try:
+            # Mark infraction as inactive in the database.
+            log.trace(f"Marking infraction #{id_} as inactive in the database.")
+            await self.bot.api_client.patch(
+                f"bot/infractions/{id_}",
+                json={"active": False}
+            )
+        except ResponseCodeError as e:
+            log.exception(f"Failed to deactivate infraction #{id_} ({type_})")
+            log_line = f"API request failed with code {e.status}."
+            log_content = mod_role.mention
+
+            # Append to an existing failure message if possible
+            if "Failure" in log_text:
+                log_text["Failure"] += f" {log_line}"
+            else:
+                log_text["Failure"] = log_line
+
+        # Cancel the expiration task.
+        if infraction["expires_at"] is not None:
+            self.cancel_task(infraction["id"])
+
+        # Send a log message to the mod log.
+        if send_log:
+            log_title = f"expiration failed" if "Failure" in log_text else "expired"
+
+            log.trace(f"Sending deactivation mod log for infraction #{id_}.")
+            await self.mod_log.send_log_message(
+                icon_url=utils.INFRACTION_ICONS[type_][1],
+                colour=Colours.soft_green,
+                title=f"Infraction {log_title}: {type_}",
+                text="\n".join(f"{k}: {v}" for k, v in log_text.items()),
+                footer=f"ID: {id_}",
+                content=log_content,
+            )
+
+        return log_text
+
+    @abstractmethod
+    async def _pardon_action(self, infraction: utils.Infraction) -> t.Optional[t.Dict[str, str]]:
+        """
+        Execute deactivation steps specific to the infraction's type and return a log dict.
+
+        If an infraction type is unsupported, return None instead.
+        """
+        raise NotImplementedError
+
+    async def _scheduled_task(self, infraction: utils.Infraction) -> None:
+        """
+        Marks an infraction expired after the delay from time of scheduling to time of expiration.
+
+        At the time of expiration, the infraction is marked as inactive on the website and the
+        expiration task is cancelled.
+        """
+        expiry = dateutil.parser.isoparse(infraction["expires_at"]).replace(tzinfo=None)
+        await time.wait_until(expiry)
+
+        await self.deactivate_infraction(infraction)
diff --git a/bot/cogs/moderation/superstarify.py b/bot/cogs/moderation/superstarify.py
index ccc6395d9..050c847ac 100644
--- a/bot/cogs/moderation/superstarify.py
+++ b/bot/cogs/moderation/superstarify.py
@@ -1,17 +1,20 @@
 import json
 import logging
 import random
+import textwrap
+import typing as t
 from pathlib import Path
 
 from discord import Colour, Embed, Member
-from discord.errors import Forbidden
-from discord.ext.commands import Bot, Cog, Context, command
+from discord.ext.commands import Cog, Context, command
 
 from bot import constants
+from bot.bot import Bot
+from bot.converters import Expiry
 from bot.utils.checks import with_role_check
 from bot.utils.time import format_infraction
 from . import utils
-from .modlog import ModLog
+from .scheduler import InfractionScheduler
 
 log = logging.getLogger(__name__)
 NICKNAME_POLICY_URL = "https://pythondiscord.com/pages/rules/#nickname-policy"
@@ -20,132 +23,96 @@ with Path("bot/resources/stars.json").open(encoding="utf-8") as stars_file:
     STAR_NAMES = json.load(stars_file)
 
 
-class Superstarify(Cog):
+class Superstarify(InfractionScheduler, Cog):
     """A set of commands to moderate terrible nicknames."""
 
     def __init__(self, bot: Bot):
-        self.bot = bot
-
-    @property
-    def modlog(self) -> ModLog:
-        """Get currently loaded ModLog cog instance."""
-        return self.bot.get_cog("ModLog")
+        super().__init__(bot, supported_infractions={"superstar"})
 
     @Cog.listener()
     async def on_member_update(self, before: Member, after: Member) -> None:
-        """
-        This event will trigger when someone changes their name.
-
-        At this point we will look up the user in our database and check whether they are allowed to
-        change their names, or if they are in superstar-prison. If they are not allowed, we will
-        change it back.
-        """
+        """Revert nickname edits if the user has an active superstarify infraction."""
         if before.display_name == after.display_name:
             return  # User didn't change their nickname. Abort!
 
         log.trace(
-            f"{before.display_name} is trying to change their nickname to {after.display_name}. "
-            "Checking if the user is in superstar-prison..."
+            f"{before} ({before.display_name}) is trying to change their nickname to "
+            f"{after.display_name}. Checking if the user is in superstar-prison..."
         )
 
         active_superstarifies = await self.bot.api_client.get(
-            'bot/infractions',
+            "bot/infractions",
             params={
-                'active': 'true',
-                'type': 'superstar',
-                'user__id': str(before.id)
+                "active": "true",
+                "type": "superstar",
+                "user__id": str(before.id)
             }
         )
 
-        if active_superstarifies:
-            [infraction] = active_superstarifies
-            forced_nick = self.get_nick(infraction['id'], before.id)
-            if after.display_name == forced_nick:
-                return  # Nick change was triggered by this event. Ignore.
-
-            log.info(
-                f"{after.display_name} is currently in superstar-prison. "
-                f"Changing the nick back to {before.display_name}."
-            )
-            await after.edit(nick=forced_nick)
-            end_timestamp_human = format_infraction(infraction['expires_at'])
-
-            try:
-                await after.send(
-                    "You have tried to change your nickname on the **Python Discord** server "
-                    f"from **{before.display_name}** to **{after.display_name}**, but as you "
-                    "are currently in superstar-prison, you do not have permission to do so. "
-                    "You will be allowed to change your nickname again at the following time:\n\n"
-                    f"**{end_timestamp_human}**."
-                )
-            except Forbidden:
-                log.warning(
-                    "The user tried to change their nickname while in superstar-prison. "
-                    "This led to the bot trying to DM the user to let them know they cannot do that, "
-                    "but the user had either blocked the bot or disabled DMs, so it was not possible "
-                    "to DM them, and a discord.errors.Forbidden error was incurred."
-                )
+        if not active_superstarifies:
+            log.trace(f"{before} has no active superstar infractions.")
+            return
+
+        infraction = active_superstarifies[0]
+        forced_nick = self.get_nick(infraction["id"], before.id)
+        if after.display_name == forced_nick:
+            return  # Nick change was triggered by this event. Ignore.
+
+        log.info(
+            f"{after.display_name} is currently in superstar-prison. "
+            f"Changing the nick back to {before.display_name}."
+        )
+        await after.edit(
+            nick=forced_nick,
+            reason=f"Superstarified member tried to escape the prison: {infraction['id']}"
+        )
+
+        notified = await utils.notify_infraction(
+            user=after,
+            infr_type="Superstarify",
+            expires_at=format_infraction(infraction["expires_at"]),
+            reason=(
+                "You have tried to change your nickname on the **Python Discord** server "
+                f"from **{before.display_name}** to **{after.display_name}**, but as you "
+                "are currently in superstar-prison, you do not have permission to do so."
+            ),
+            icon_url=utils.INFRACTION_ICONS["superstar"][0]
+        )
+
+        if not notified:
+            log.warning("Failed to DM user about why they cannot change their nickname.")
 
     @Cog.listener()
     async def on_member_join(self, member: Member) -> None:
-        """
-        This event will trigger when someone (re)joins the server.
-
-        At this point we will look up the user in our database and check whether they are in
-        superstar-prison. If so, we will change their name back to the forced nickname.
-        """
+        """Reapply active superstar infractions for returning members."""
         active_superstarifies = await self.bot.api_client.get(
-            'bot/infractions',
+            "bot/infractions",
             params={
-                'active': 'true',
-                'type': 'superstar',
-                'user__id': member.id
+                "active": "true",
+                "type": "superstar",
+                "user__id": member.id
             }
         )
 
         if active_superstarifies:
-            [infraction] = active_superstarifies
-            forced_nick = self.get_nick(infraction['id'], member.id)
-            await member.edit(nick=forced_nick)
-            end_timestamp_human = format_infraction(infraction['expires_at'])
-
-            try:
-                await member.send(
-                    "You have left and rejoined the **Python Discord** server, effectively resetting "
-                    f"your nickname from **{forced_nick}** to **{member.name}**, "
-                    "but as you are currently in superstar-prison, you do not have permission to do so. "
-                    "Therefore your nickname was automatically changed back. You will be allowed to "
-                    "change your nickname again at the following time:\n\n"
-                    f"**{end_timestamp_human}**."
-                )
-            except Forbidden:
-                log.warning(
-                    "The user left and rejoined the server while in superstar-prison. "
-                    "This led to the bot trying to DM the user to let them know their name was restored, "
-                    "but the user had either blocked the bot or disabled DMs, so it was not possible "
-                    "to DM them, and a discord.errors.Forbidden error was incurred."
-                )
-
-            # Log to the mod_log channel
-            log.trace("Logging to the #mod-log channel. This could fail because of channel permissions.")
-            mod_log_message = (
-                f"**{member.name}#{member.discriminator}** (`{member.id}`)\n\n"
-                f"Superstarified member potentially tried to escape the prison.\n"
-                f"Restored enforced nickname: `{forced_nick}`\n"
-                f"Superstardom ends: **{end_timestamp_human}**"
-            )
-            await self.modlog.send_log_message(
-                icon_url=constants.Icons.user_update,
-                colour=Colour.gold(),
-                title="Superstar member rejoined server",
-                text=mod_log_message,
-                thumbnail=member.avatar_url_as(static_format="png")
+            infraction = active_superstarifies[0]
+            action = member.edit(
+                nick=self.get_nick(infraction["id"], member.id),
+                reason=f"Superstarified member tried to escape the prison: {infraction['id']}"
             )
 
-    @command(name='superstarify', aliases=('force_nick', 'star'))
-    async def superstarify(self, ctx: Context, member: Member, duration: utils.Expiry, reason: str = None) -> None:
+            await self.reapply_infraction(infraction, action)
+
+    @command(name="superstarify", aliases=("force_nick", "star"))
+    async def superstarify(
+        self,
+        ctx: Context,
+        member: Member,
+        duration: Expiry,
+        reason: str = None
+    ) -> None:
         """
-        Force a random superstar name (like Taylor Swift) to be the user's nickname for a specified duration.
+        Temporarily force a random superstar name (like Taylor Swift) to be the user's nickname.
 
         A unit of time should be appended to the duration.
         Units (∗case-sensitive):
@@ -165,91 +132,103 @@ class Superstarify(Cog):
         if await utils.has_active_infraction(ctx, member, "superstar"):
             return
 
-        reason = reason or ('old nick: ' + member.display_name)
-        infraction = await utils.post_infraction(ctx, member, 'superstar', reason, expires_at=duration)
-        forced_nick = self.get_nick(infraction['id'], member.id)
-        expiry_str = format_infraction(infraction["expires_at"])
+        # Post the infraction to the API
+        reason = reason or f"old nick: {member.display_name}"
+        infraction = await utils.post_infraction(ctx, member, "superstar", reason, duration, active=True)
+        id_ = infraction["id"]
 
-        embed = Embed()
-        embed.title = "Congratulations!"
-        embed.description = (
-            f"Your previous nickname, **{member.display_name}**, was so bad that we have decided to change it. "
-            f"Your new nickname will be **{forced_nick}**.\n\n"
-            f"You will be unable to change your nickname until \n**{expiry_str}**.\n\n"
-            "If you're confused by this, please read our "
-            f"[official nickname policy]({NICKNAME_POLICY_URL})."
-        )
+        old_nick = member.display_name
+        forced_nick = self.get_nick(id_, member.id)
+        expiry_str = format_infraction(infraction["expires_at"])
 
-        # Log to the mod_log channel
-        log.trace("Logging to the #mod-log channel. This could fail because of channel permissions.")
-        mod_log_message = (
-            f"**{member.name}#{member.discriminator}** (`{member.id}`)\n\n"
-            f"Superstarified by **{ctx.author.name}**\n"
-            f"Old nickname: `{member.display_name}`\n"
-            f"New nickname: `{forced_nick}`\n"
-            f"Superstardom ends: **{expiry_str}**"
-        )
-        await self.modlog.send_log_message(
-            icon_url=constants.Icons.user_update,
-            colour=Colour.gold(),
-            title="Member Achieved Superstardom",
-            text=mod_log_message,
-            thumbnail=member.avatar_url_as(static_format="png")
-        )
+        # Apply the infraction and schedule the expiration task.
+        log.debug(f"Changing nickname of {member} to {forced_nick}.")
+        self.mod_log.ignore(constants.Event.member_update, member.id)
+        await member.edit(nick=forced_nick, reason=reason)
+        self.schedule_task(ctx.bot.loop, id_, infraction)
 
+        # Send a DM to the user to notify them of their new infraction.
         await utils.notify_infraction(
             user=member,
             infr_type="Superstarify",
             expires_at=expiry_str,
+            icon_url=utils.INFRACTION_ICONS["superstar"][0],
             reason=f"Your nickname didn't comply with our [nickname policy]({NICKNAME_POLICY_URL})."
         )
 
-        # Change the nick and return the embed
-        log.trace("Changing the users nickname and sending the embed.")
-        await member.edit(nick=forced_nick)
+        # Send an embed with the infraction information to the invoking context.
+        log.trace(f"Sending superstar #{id_} embed.")
+        embed = Embed(
+            title="Congratulations!",
+            colour=constants.Colours.soft_orange,
+            description=(
+                f"Your previous nickname, **{old_nick}**, "
+                f"was so bad that we have decided to change it. "
+                f"Your new nickname will be **{forced_nick}**.\n\n"
+                f"You will be unable to change your nickname until **{expiry_str}**.\n\n"
+                "If you're confused by this, please read our "
+                f"[official nickname policy]({NICKNAME_POLICY_URL})."
+            )
+        )
         await ctx.send(embed=embed)
 
-    @command(name='unsuperstarify', aliases=('release_nick', 'unstar'))
-    async def unsuperstarify(self, ctx: Context, member: Member) -> None:
-        """Remove the superstarify entry from our database, allowing the user to change their nickname."""
-        log.debug(f"Attempting to unsuperstarify the following user: {member.display_name}")
+        # Log to the mod log channel.
+        log.trace(f"Sending apply mod log for superstar #{id_}.")
+        await self.mod_log.send_log_message(
+            icon_url=utils.INFRACTION_ICONS["superstar"][0],
+            colour=Colour.gold(),
+            title="Member achieved superstardom",
+            thumbnail=member.avatar_url_as(static_format="png"),
+            text=textwrap.dedent(f"""
+                Member: {member.mention} (`{member.id}`)
+                Actor: {ctx.message.author}
+                Reason: {reason}
+                Expires: {expiry_str}
+                Old nickname: `{old_nick}`
+                New nickname: `{forced_nick}`
+            """),
+            footer=f"ID {id_}"
+        )
 
-        embed = Embed()
-        embed.colour = Colour.blurple()
+    @command(name="unsuperstarify", aliases=("release_nick", "unstar"))
+    async def unsuperstarify(self, ctx: Context, member: Member) -> None:
+        """Remove the superstarify infraction and allow the user to change their nickname."""
+        await self.pardon_infraction(ctx, "superstar", member)
 
-        active_superstarifies = await self.bot.api_client.get(
-            'bot/infractions',
-            params={
-                'active': 'true',
-                'type': 'superstar',
-                'user__id': str(member.id)
-            }
-        )
-        if not active_superstarifies:
-            await ctx.send(":x: There is no active superstarify infraction for this user.")
+    async def _pardon_action(self, infraction: utils.Infraction) -> t.Optional[t.Dict[str, str]]:
+        """Pardon a superstar infraction and return a log dict."""
+        if infraction["type"] != "superstar":
             return
 
-        [infraction] = active_superstarifies
-        await self.bot.api_client.patch(
-            'bot/infractions/' + str(infraction['id']),
-            json={'active': False}
-        )
-
-        embed = Embed()
-        embed.description = "User has been released from superstar-prison."
-        embed.title = random.choice(constants.POSITIVE_REPLIES)
+        guild = self.bot.get_guild(constants.Guild.id)
+        user = guild.get_member(infraction["user"])
 
-        await utils.notify_pardon(
-            user=member,
-            title="You are no longer superstarified.",
-            content="You may now change your nickname on the server."
+        # Don't bother sending a notification if the user left the guild.
+        if not user:
+            log.debug(
+                "User left the guild and therefore won't be notified about superstar "
+                f"{infraction['id']} pardon."
+            )
+            return {}
+
+        # DM the user about the expiration.
+        notified = await utils.notify_pardon(
+            user=user,
+            title="You are no longer superstarified",
+            content="You may now change your nickname on the server.",
+            icon_url=utils.INFRACTION_ICONS["superstar"][1]
         )
-        log.trace(f"{member.display_name} was successfully released from superstar-prison.")
-        await ctx.send(embed=embed)
+
+        return {
+            "Member": f"{user.mention}(`{user.id}`)",
+            "DM": "Sent" if notified else "**Failed**"
+        }
 
     @staticmethod
     def get_nick(infraction_id: int, member_id: int) -> str:
         """Randomly select a nickname from the Superstarify nickname list."""
+        log.trace(f"Choosing a random nickname for superstar #{infraction_id}.")
+
         rng = random.Random(str(infraction_id) + str(member_id))
         return rng.choice(STAR_NAMES)
 
diff --git a/bot/cogs/moderation/utils.py b/bot/cogs/moderation/utils.py
index 788a40d40..5052b9048 100644
--- a/bot/cogs/moderation/utils.py
+++ b/bot/cogs/moderation/utils.py
@@ -4,60 +4,72 @@ import typing as t
 from datetime import datetime
 
 import discord
-from discord.ext import commands
 from discord.ext.commands import Context
 
 from bot.api import ResponseCodeError
 from bot.constants import Colours, Icons
-from bot.converters import Duration, ISODateTime
 
 log = logging.getLogger(__name__)
 
 # apply icon, pardon icon
 INFRACTION_ICONS = {
-    "mute": (Icons.user_mute, Icons.user_unmute),
-    "kick": (Icons.sign_out, None),
     "ban": (Icons.user_ban, Icons.user_unban),
-    "warning": (Icons.user_warn, None),
+    "kick": (Icons.sign_out, None),
+    "mute": (Icons.user_mute, Icons.user_unmute),
     "note": (Icons.user_warn, None),
+    "superstar": (Icons.superstarify, Icons.unsuperstarify),
+    "warning": (Icons.user_warn, None),
 }
 RULES_URL = "https://pythondiscord.com/pages/rules"
 APPEALABLE_INFRACTIONS = ("ban", "mute")
 
-UserTypes = t.Union[discord.Member, discord.User]
-MemberObject = t.Union[UserTypes, discord.Object]
+# Type aliases
+UserObject = t.Union[discord.Member, discord.User]
+UserSnowflake = t.Union[UserObject, discord.Object]
 Infraction = t.Dict[str, t.Union[str, int, bool]]
-Expiry = t.Union[Duration, ISODateTime]
 
 
-def proxy_user(user_id: str) -> discord.Object:
+async def post_user(ctx: Context, user: UserSnowflake) -> t.Optional[dict]:
     """
-    Create a proxy user object from the given id.
+    Create a new user in the database.
 
-    Used when a Member or User object cannot be resolved.
+    Used when an infraction needs to be applied on a user absent in the guild.
     """
-    try:
-        user_id = int(user_id)
-    except ValueError:
-        raise commands.BadArgument
+    log.trace(f"Attempting to add user {user.id} to the database.")
+
+    if not isinstance(user, (discord.Member, discord.User)):
+        log.warning("The user being added to the DB is not a Member or User object.")
 
-    user = discord.Object(user_id)
-    user.mention = user.id
-    user.avatar_url_as = lambda static_format: None
+    payload = {
+        'avatar_hash': getattr(user, 'avatar', 0),
+        'discriminator': int(getattr(user, 'discriminator', 0)),
+        'id': user.id,
+        'in_guild': False,
+        'name': getattr(user, 'name', 'Name unknown'),
+        'roles': []
+    }
 
-    return user
+    try:
+        response = await ctx.bot.api_client.post('bot/users', json=payload)
+        log.info(f"User {user.id} added to the DB.")
+        return response
+    except ResponseCodeError as e:
+        log.error(f"Failed to add user {user.id} to the DB. {e}")
+        await ctx.send(f":x: The attempt to add the user to the DB failed: status {e.status}")
 
 
 async def post_infraction(
     ctx: Context,
-    user: MemberObject,
+    user: UserSnowflake,
     infr_type: str,
     reason: str,
     expires_at: datetime = None,
     hidden: bool = False,
-    active: bool = True,
+    active: bool = True
 ) -> t.Optional[dict]:
     """Posts an infraction to the API."""
+    log.trace(f"Posting {infr_type} infraction for {user} to the API.")
+
     payload = {
         "actor": ctx.message.author.id,
         "hidden": hidden,
@@ -69,28 +81,26 @@ async def post_infraction(
     if expires_at:
         payload['expires_at'] = expires_at.isoformat()
 
-    try:
-        response = await ctx.bot.api_client.post('bot/infractions', json=payload)
-    except ResponseCodeError as exp:
-        if exp.status == 400 and 'user' in exp.response_json:
-            log.info(
-                f"{ctx.author} tried to add a {infr_type} infraction to `{user.id}`, "
-                "but that user id was not found in the database."
-            )
-            await ctx.send(
-                f":x: Cannot add infraction, the specified user is not known to the database."
-            )
-            return
-        else:
-            log.exception("An unexpected ResponseCodeError occurred while adding an infraction:")
-            await ctx.send(":x: There was an error adding the infraction.")
-            return
-
-    return response
-
-
-async def has_active_infraction(ctx: Context, user: MemberObject, infr_type: str) -> bool:
+    # Try to apply the infraction. If it fails because the user doesn't exist, try to add it.
+    for should_post_user in (True, False):
+        try:
+            response = await ctx.bot.api_client.post('bot/infractions', json=payload)
+            return response
+        except ResponseCodeError as e:
+            if e.status == 400 and 'user' in e.response_json:
+                # Only one attempt to add the user to the database, not two:
+                if not should_post_user or await post_user(ctx, user) is None:
+                    return
+            else:
+                log.exception(f"Unexpected error while adding an infraction for {user}:")
+                await ctx.send(f":x: There was an error adding the infraction: status {e.status}.")
+                return
+
+
+async def has_active_infraction(ctx: Context, user: UserSnowflake, infr_type: str) -> bool:
     """Checks if a user already has an active infraction of the given type."""
+    log.trace(f"Checking if {user} has active infractions of type {infr_type}.")
+
     active_infractions = await ctx.bot.api_client.get(
         'bot/infractions',
         params={
@@ -100,23 +110,27 @@ async def has_active_infraction(ctx: Context, user: MemberObject, infr_type: str
         }
     )
     if active_infractions:
+        log.trace(f"{user} has active infractions of type {infr_type}.")
         await ctx.send(
             f":x: According to my records, this user already has a {infr_type} infraction. "
             f"See infraction **#{active_infractions[0]['id']}**."
         )
         return True
     else:
+        log.trace(f"{user} does not have active infractions of type {infr_type}.")
         return False
 
 
 async def notify_infraction(
-    user: UserTypes,
+    user: UserObject,
     infr_type: str,
     expires_at: t.Optional[str] = None,
     reason: t.Optional[str] = None,
     icon_url: str = Icons.token_removed
 ) -> bool:
     """DM a user about their new infraction and return True if the DM is successful."""
+    log.trace(f"Sending {user} a DM about their {infr_type} infraction.")
+
     embed = discord.Embed(
         description=textwrap.dedent(f"""
             **Type:** {infr_type.capitalize()}
@@ -126,7 +140,7 @@ async def notify_infraction(
         colour=Colours.soft_red
     )
 
-    embed.set_author(name="Infraction Information", icon_url=icon_url, url=RULES_URL)
+    embed.set_author(name="Infraction information", icon_url=icon_url, url=RULES_URL)
     embed.title = f"Please review our rules over at {RULES_URL}"
     embed.url = RULES_URL
 
@@ -139,12 +153,14 @@ async def notify_infraction(
 
 
 async def notify_pardon(
-    user: UserTypes,
+    user: UserObject,
     title: str,
     content: str,
     icon_url: str = Icons.user_verified
 ) -> bool:
     """DM a user about their pardoned infraction and return True if the DM is successful."""
+    log.trace(f"Sending {user} a DM about their pardoned infraction.")
+
     embed = discord.Embed(
         description=content,
         colour=Colours.soft_green
@@ -155,7 +171,7 @@ async def notify_pardon(
     return await send_private_embed(user, embed)
 
 
-async def send_private_embed(user: UserTypes, embed: discord.Embed) -> bool:
+async def send_private_embed(user: UserObject, embed: discord.Embed) -> bool:
     """
     A helper method for sending an embed to a user's DMs.
 
diff --git a/bot/cogs/off_topic_names.py b/bot/cogs/off_topic_names.py
index 2977e4ebb..bf777ea5a 100644
--- a/bot/cogs/off_topic_names.py
+++ b/bot/cogs/off_topic_names.py
@@ -4,9 +4,10 @@ import logging
 from datetime import datetime, timedelta
 
 from discord import Colour, Embed
-from discord.ext.commands import BadArgument, Bot, Cog, Context, Converter, group
+from discord.ext.commands import BadArgument, Cog, Context, Converter, group
 
 from bot.api import ResponseCodeError
+from bot.bot import Bot
 from bot.constants import Channels, MODERATION_ROLES
 from bot.decorators import with_role
 from bot.pagination import LinePaginator
@@ -24,6 +25,9 @@ class OffTopicName(Converter):
         """Attempt to replace any invalid characters with their approximate Unicode equivalent."""
         allowed_characters = "ABCDEFGHIJKLMNOPQRSTUVWXYZ!?'`-"
 
+        # Chain multiple words to a single one
+        argument = "-".join(argument.split())
+
         if not (2 <= len(argument) <= 96):
             raise BadArgument("Channel name must be between 2 and 96 chars long")
 
@@ -97,30 +101,47 @@ class OffTopicNames(Cog):
 
     @otname_group.command(name='add', aliases=('a',))
     @with_role(*MODERATION_ROLES)
-    async def add_command(self, ctx: Context, *names: OffTopicName) -> None:
-        """Adds a new off-topic name to the rotation."""
-        # Chain multiple words to a single one
-        name = "-".join(names)
+    async def add_command(self, ctx: Context, *, name: OffTopicName) -> None:
+        """
+        Adds a new off-topic name to the rotation.
 
-        await self.bot.api_client.post(f'bot/off-topic-channel-names', params={'name': name})
-        log.info(
-            f"{ctx.author.name}#{ctx.author.discriminator}"
-            f" added the off-topic channel name '{name}"
-        )
+        The name is not added if it is too similar to an existing name.
+        """
+        existing_names = await self.bot.api_client.get('bot/off-topic-channel-names')
+        close_match = difflib.get_close_matches(name, existing_names, n=1, cutoff=0.8)
+
+        if close_match:
+            match = close_match[0]
+            log.info(
+                f"{ctx.author} tried to add channel name '{name}' but it was too similar to '{match}'"
+            )
+            await ctx.send(
+                f":x: The channel name `{name}` is too similar to `{match}`, and thus was not added. "
+                "Use `!otn forceadd` to override this check."
+            )
+        else:
+            await self._add_name(ctx, name)
+
+    @otname_group.command(name='forceadd', aliases=('fa',))
+    @with_role(*MODERATION_ROLES)
+    async def force_add_command(self, ctx: Context, *, name: OffTopicName) -> None:
+        """Forcefully adds a new off-topic name to the rotation."""
+        await self._add_name(ctx, name)
+
+    async def _add_name(self, ctx: Context, name: str) -> None:
+        """Adds an off-topic channel name to the site storage."""
+        await self.bot.api_client.post('bot/off-topic-channel-names', params={'name': name})
+
+        log.info(f"{ctx.author} added the off-topic channel name '{name}'")
         await ctx.send(f":ok_hand: Added `{name}` to the names list.")
 
     @otname_group.command(name='delete', aliases=('remove', 'rm', 'del', 'd'))
     @with_role(*MODERATION_ROLES)
-    async def delete_command(self, ctx: Context, *names: OffTopicName) -> None:
+    async def delete_command(self, ctx: Context, *, name: OffTopicName) -> None:
         """Removes a off-topic name from the rotation."""
-        # Chain multiple words to a single one
-        name = "-".join(names)
-
         await self.bot.api_client.delete(f'bot/off-topic-channel-names/{name}')
-        log.info(
-            f"{ctx.author.name}#{ctx.author.discriminator}"
-            f" deleted the off-topic channel name '{name}"
-        )
+
+        log.info(f"{ctx.author} deleted the off-topic channel name '{name}'")
         await ctx.send(f":ok_hand: Removed `{name}` from the names list.")
 
     @otname_group.command(name='list', aliases=('l',))
@@ -152,7 +173,7 @@ class OffTopicNames(Cog):
         close_matches = difflib.get_close_matches(query, result, n=10, cutoff=0.70)
         lines = sorted(f"• {name}" for name in in_matches.union(close_matches))
         embed = Embed(
-            title=f"Query results",
+            title="Query results",
             colour=Colour.blue()
         )
 
@@ -164,6 +185,5 @@ class OffTopicNames(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Off topic names cog load."""
+    """Load the OffTopicNames cog."""
     bot.add_cog(OffTopicNames(bot))
-    log.info("Cog loaded: OffTopicNames")
diff --git a/bot/cogs/reddit.py b/bot/cogs/reddit.py
index 0f575cece..aa487f18e 100644
--- a/bot/cogs/reddit.py
+++ b/bot/cogs/reddit.py
@@ -2,39 +2,121 @@ import asyncio
 import logging
 import random
 import textwrap
+from collections import namedtuple
 from datetime import datetime, timedelta
 from typing import List
 
-from discord import Colour, Embed, Message, TextChannel
-from discord.ext.commands import Bot, Cog, Context, group
+from aiohttp import BasicAuth, ClientError
+from discord import Colour, Embed, TextChannel
+from discord.ext.commands import Cog, Context, group
+from discord.ext.tasks import loop
 
-from bot.constants import Channels, ERROR_REPLIES, Reddit as RedditConfig, STAFF_ROLES
+from bot.bot import Bot
+from bot.constants import Channels, ERROR_REPLIES, Emojis, Reddit as RedditConfig, STAFF_ROLES, Webhooks
 from bot.converters import Subreddit
 from bot.decorators import with_role
 from bot.pagination import LinePaginator
 
 log = logging.getLogger(__name__)
 
+AccessToken = namedtuple("AccessToken", ["token", "expires_at"])
+
 
 class Reddit(Cog):
     """Track subreddit posts and show detailed statistics about them."""
 
-    HEADERS = {"User-Agent": "Discord Bot: PythonDiscord (https://pythondiscord.com/)"}
+    HEADERS = {"User-Agent": "python3:python-discord/bot:1.0.0 (by /u/PythonDiscord)"}
     URL = "https://www.reddit.com"
-    MAX_FETCH_RETRIES = 3
+    OAUTH_URL = "https://oauth.reddit.com"
+    MAX_RETRIES = 3
 
     def __init__(self, bot: Bot):
         self.bot = bot
 
-        self.reddit_channel = None
+        self.webhook = None
+        self.access_token = None
+        self.client_auth = BasicAuth(RedditConfig.client_id, RedditConfig.secret)
+
+        bot.loop.create_task(self.init_reddit_ready())
+        self.auto_poster_loop.start()
+
+    def cog_unload(self) -> None:
+        """Stop the loop task and revoke the access token when the cog is unloaded."""
+        self.auto_poster_loop.cancel()
+        if self.access_token.expires_at < datetime.utcnow():
+            self.revoke_access_token()
+
+    async def init_reddit_ready(self) -> None:
+        """Sets the reddit webhook when the cog is loaded."""
+        await self.bot.wait_until_ready()
+        if not self.webhook:
+            self.webhook = await self.bot.fetch_webhook(Webhooks.reddit)
+
+    @property
+    def channel(self) -> TextChannel:
+        """Get the #reddit channel object from the bot's cache."""
+        return self.bot.get_channel(Channels.reddit)
+
+    async def get_access_token(self) -> None:
+        """
+        Get a Reddit API OAuth2 access token and assign it to self.access_token.
+
+        A token is valid for 1 hour. There will be MAX_RETRIES to get a token, after which the cog
+        will be unloaded and a ClientError raised if retrieval was still unsuccessful.
+        """
+        for i in range(1, self.MAX_RETRIES + 1):
+            response = await self.bot.http_session.post(
+                url=f"{self.URL}/api/v1/access_token",
+                headers=self.HEADERS,
+                auth=self.client_auth,
+                data={
+                    "grant_type": "client_credentials",
+                    "duration": "temporary"
+                }
+            )
+
+            if response.status == 200 and response.content_type == "application/json":
+                content = await response.json()
+                expiration = int(content["expires_in"]) - 60  # Subtract 1 minute for leeway.
+                self.access_token = AccessToken(
+                    token=content["access_token"],
+                    expires_at=datetime.utcnow() + timedelta(seconds=expiration)
+                )
+
+                log.debug(f"New token acquired; expires on {self.access_token.expires_at}")
+                return
+            else:
+                log.debug(
+                    f"Failed to get an access token: "
+                    f"status {response.status} & content type {response.content_type}; "
+                    f"retrying ({i}/{self.MAX_RETRIES})"
+                )
 
-        self.prev_lengths = {}
-        self.last_ids = {}
+            await asyncio.sleep(3)
 
-        self.new_posts_task = None
-        self.top_weekly_posts_task = None
+        self.bot.remove_cog(self.qualified_name)
+        raise ClientError("Authentication with the Reddit API failed. Unloading the cog.")
+
+    async def revoke_access_token(self) -> None:
+        """
+        Revoke the OAuth2 access token for the Reddit API.
+
+        For security reasons, it's good practice to revoke the token when it's no longer being used.
+        """
+        response = await self.bot.http_session.post(
+            url=f"{self.URL}/api/v1/revoke_token",
+            headers=self.HEADERS,
+            auth=self.client_auth,
+            data={
+                "token": self.access_token.token,
+                "token_type_hint": "access_token"
+            }
+        )
 
-        self.bot.loop.create_task(self.init_reddit_polling())
+        if response.status == 204 and response.content_type == "application/json":
+            self.access_token = None
+        else:
+            log.warning(f"Unable to revoke access token: status {response.status}.")
 
     async def fetch_posts(self, route: str, *, amount: int = 25, params: dict = None) -> List[dict]:
         """A helper method to fetch a certain amount of Reddit posts at a given route."""
@@ -42,14 +124,15 @@ class Reddit(Cog):
         if not 25 >= amount > 0:
             raise ValueError("Invalid amount of subreddit posts requested.")
 
-        if params is None:
-            params = {}
+        # Renew the token if necessary.
+        if not self.access_token or self.access_token.expires_at < datetime.utcnow():
+            await self.get_access_token()
 
-        url = f"{self.URL}/{route}.json"
-        for _ in range(self.MAX_FETCH_RETRIES):
+        url = f"{self.OAUTH_URL}/{route}"
+        for _ in range(self.MAX_RETRIES):
             response = await self.bot.http_session.get(
                 url=url,
-                headers=self.HEADERS,
+                headers={**self.HEADERS, "Authorization": f"bearer {self.access_token.token}"},
                 params=params
             )
             if response.status == 200 and response.content_type == 'application/json':
@@ -63,23 +146,22 @@ class Reddit(Cog):
         log.debug(f"Invalid response from: {url} - status code {response.status}, mimetype {response.content_type}")
         return list()  # Failed to get appropriate response within allowed number of retries.
 
-    async def send_top_posts(
-        self, channel: TextChannel, subreddit: Subreddit, content: str = None, time: str = "all"
-    ) -> Message:
-        """Create an embed for the top posts, then send it in a given TextChannel."""
-        # Create the new spicy embed.
-        embed = Embed()
-        embed.description = ""
-
-        # Get the posts
-        async with channel.typing():
-            posts = await self.fetch_posts(
-                route=f"{subreddit}/top",
-                amount=5,
-                params={
-                    "t": time
-                }
-            )
+    async def get_top_posts(self, subreddit: Subreddit, time: str = "all", amount: int = 5) -> Embed:
+        """
+        Get the top amount of posts for a given subreddit within a specified timeframe.
+
+        A time of "all" will get posts from all time, "day" will get top daily posts and "week" will get the top
+        weekly posts.
+
+        The amount should be between 0 and 25 as Reddit's JSON requests only provide 25 posts at most.
+        """
+        embed = Embed(description="")
+
+        posts = await self.fetch_posts(
+            route=f"{subreddit}/top",
+            amount=amount,
+            params={"t": time}
+        )
 
         if not posts:
             embed.title = random.choice(ERROR_REPLIES)
@@ -89,9 +171,7 @@ class Reddit(Cog):
                 "If this problem persists, please let us know."
             )
 
-            return await channel.send(
-                embed=embed
-            )
+            return embed
 
         for post in posts:
             data = post["data"]
@@ -109,109 +189,58 @@ class Reddit(Cog):
             link = self.URL + data["permalink"]
 
             embed.description += (
-                f"[**{title}**]({link})\n"
+                f"**[{title}]({link})**\n"
                 f"{text}"
-                f"| {ups} upvotes | {comments} comments | u/{author} | {subreddit} |\n\n"
+                f"{Emojis.upvotes} {ups} {Emojis.comments} {comments} {Emojis.user} {author}\n\n"
             )
 
         embed.colour = Colour.blurple()
+        return embed
 
-        return await channel.send(
-            content=content,
-            embed=embed
-        )
-
-    async def poll_new_posts(self) -> None:
-        """Periodically search for new subreddit posts."""
-        while True:
-            await asyncio.sleep(RedditConfig.request_delay)
-
-            for subreddit in RedditConfig.subreddits:
-                # Make a HEAD request to the subreddit
-                head_response = await self.bot.http_session.head(
-                    url=f"{self.URL}/{subreddit}/new.rss",
-                    headers=self.HEADERS
-                )
-
-                content_length = head_response.headers["content-length"]
-
-                # If the content is the same size as before, assume there's no new posts.
-                if content_length == self.prev_lengths.get(subreddit, None):
-                    continue
-
-                self.prev_lengths[subreddit] = content_length
-
-                # Now we can actually fetch the new data
-                posts = await self.fetch_posts(f"{subreddit}/new")
-                new_posts = []
-
-                # Only show new posts if we've checked before.
-                if subreddit in self.last_ids:
-                    for post in posts:
-                        data = post["data"]
-
-                        # Convert the ID to an integer for easy comparison.
-                        int_id = int(data["id"], 36)
-
-                        # If we've already seen this post, finish checking
-                        if int_id <= self.last_ids[subreddit]:
-                            break
-
-                        embed_data = {
-                            "title": textwrap.shorten(data["title"], width=64, placeholder="..."),
-                            "text": textwrap.shorten(data["selftext"], width=128, placeholder="..."),
-                            "url": self.URL + data["permalink"],
-                            "author": data["author"]
-                        }
-
-                        new_posts.append(embed_data)
-
-                self.last_ids[subreddit] = int(posts[0]["data"]["id"], 36)
+    @loop()
+    async def auto_poster_loop(self) -> None:
+        """Post the top 5 posts daily, and the top 5 posts weekly."""
+        # once we upgrade to d.py 1.3 this can be removed and the loop can use the `time=datetime.time.min` parameter
+        now = datetime.utcnow()
+        tomorrow = now + timedelta(days=1)
+        midnight_tomorrow = tomorrow.replace(hour=0, minute=0, second=0)
+        seconds_until = (midnight_tomorrow - now).total_seconds()
 
-                # Send all of the new posts as spicy embeds
-                for data in new_posts:
-                    embed = Embed()
+        await asyncio.sleep(seconds_until)
 
-                    embed.title = data["title"]
-                    embed.url = data["url"]
-                    embed.description = data["text"]
-                    embed.set_footer(text=f"Posted by u/{data['author']} in {subreddit}")
-                    embed.colour = Colour.blurple()
-
-                    await self.reddit_channel.send(embed=embed)
+        await self.bot.wait_until_ready()
+        if not self.webhook:
+            await self.bot.fetch_webhook(Webhooks.reddit)
 
-                log.trace(f"Sent {len(new_posts)} new {subreddit} posts to channel {self.reddit_channel.id}.")
+        if datetime.utcnow().weekday() == 0:
+            await self.top_weekly_posts()
+            # if it's a monday send the top weekly posts
 
-    async def poll_top_weekly_posts(self) -> None:
-        """Post a summary of the top posts every week."""
-        while True:
-            now = datetime.utcnow()
+        for subreddit in RedditConfig.subreddits:
+            top_posts = await self.get_top_posts(subreddit=subreddit, time="day")
+            await self.webhook.send(username=f"{subreddit} Top Daily Posts", embed=top_posts)
 
-            # Calculate the amount of seconds until midnight next monday.
-            monday = now + timedelta(days=7 - now.weekday())
-            monday = monday.replace(hour=0, minute=0, second=0)
-            until_monday = (monday - now).total_seconds()
+    async def top_weekly_posts(self) -> None:
+        """Post a summary of the top posts."""
+        for subreddit in RedditConfig.subreddits:
+            # Send and pin the new weekly posts.
+            top_posts = await self.get_top_posts(subreddit=subreddit, time="week")
 
-            await asyncio.sleep(until_monday)
+            message = await self.webhook.send(wait=True, username=f"{subreddit} Top Weekly Posts", embed=top_posts)
 
-            for subreddit in RedditConfig.subreddits:
-                # Send and pin the new weekly posts.
-                message = await self.send_top_posts(
-                    channel=self.reddit_channel,
-                    subreddit=subreddit,
-                    content=f"This week's top {subreddit} posts have arrived!",
-                    time="week"
-                )
+            if subreddit.lower() == "r/python":
+                if not self.channel:
+                    log.warning("Failed to get #reddit channel to remove pins in the weekly loop.")
+                    return
 
-                if subreddit.lower() == "r/python":
-                    # Remove the oldest pins so that only 5 remain at most.
-                    pins = await self.reddit_channel.pins()
+                # Remove the oldest pins so that only 12 remain at most.
+                pins = await self.channel.pins()
 
-                    while len(pins) >= 5:
-                        await pins[-1].unpin()
-                        del pins[-1]
+                while len(pins) >= 12:
+                    await pins[-1].unpin()
+                    del pins[-1]
 
-                    await message.pin()
+                await message.pin()
 
     @group(name="reddit", invoke_without_command=True)
     async def reddit_group(self, ctx: Context) -> None:
@@ -221,32 +250,26 @@ class Reddit(Cog):
     @reddit_group.command(name="top")
     async def top_command(self, ctx: Context, subreddit: Subreddit = "r/Python") -> None:
         """Send the top posts of all time from a given subreddit."""
-        await self.send_top_posts(
-            channel=ctx.channel,
-            subreddit=subreddit,
-            content=f"Here are the top {subreddit} posts of all time!",
-            time="all"
-        )
+        async with ctx.typing():
+            embed = await self.get_top_posts(subreddit=subreddit, time="all")
+
+        await ctx.send(content=f"Here are the top {subreddit} posts of all time!", embed=embed)
 
     @reddit_group.command(name="daily")
     async def daily_command(self, ctx: Context, subreddit: Subreddit = "r/Python") -> None:
         """Send the top posts of today from a given subreddit."""
-        await self.send_top_posts(
-            channel=ctx.channel,
-            subreddit=subreddit,
-            content=f"Here are today's top {subreddit} posts!",
-            time="day"
-        )
+        async with ctx.typing():
+            embed = await self.get_top_posts(subreddit=subreddit, time="day")
+
+        await ctx.send(content=f"Here are today's top {subreddit} posts!", embed=embed)
 
     @reddit_group.command(name="weekly")
     async def weekly_command(self, ctx: Context, subreddit: Subreddit = "r/Python") -> None:
         """Send the top posts of this week from a given subreddit."""
-        await self.send_top_posts(
-            channel=ctx.channel,
-            subreddit=subreddit,
-            content=f"Here are this week's top {subreddit} posts!",
-            time="week"
-        )
+        async with ctx.typing():
+            embed = await self.get_top_posts(subreddit=subreddit, time="week")
+
+        await ctx.send(content=f"Here are this week's top {subreddit} posts!", embed=embed)
 
     @with_role(*STAFF_ROLES)
     @reddit_group.command(name="subreddits", aliases=("subs",))
@@ -264,21 +287,7 @@ class Reddit(Cog):
             max_lines=15
         )
 
-    async def init_reddit_polling(self) -> None:
-        """Initiate reddit post event loop."""
-        await self.bot.wait_until_ready()
-        self.reddit_channel = await self.bot.fetch_channel(Channels.reddit)
-
-        if self.reddit_channel is not None:
-            if self.new_posts_task is None:
-                self.new_posts_task = self.bot.loop.create_task(self.poll_new_posts())
-            if self.top_weekly_posts_task is None:
-                self.top_weekly_posts_task = self.bot.loop.create_task(self.poll_top_weekly_posts())
-        else:
-            log.warning("Couldn't locate a channel for subreddit relaying.")
-
 
 def setup(bot: Bot) -> None:
-    """Reddit cog load."""
+    """Load the Reddit cog."""
     bot.add_cog(Reddit(bot))
-    log.info("Cog loaded: Reddit")
diff --git a/bot/cogs/reminders.py b/bot/cogs/reminders.py
index b54622306..45bf9a8f4 100644
--- a/bot/cogs/reminders.py
+++ b/bot/cogs/reminders.py
@@ -2,14 +2,15 @@ import asyncio
 import logging
 import random
 import textwrap
-from datetime import datetime
+from datetime import datetime, timedelta
 from operator import itemgetter
 from typing import Optional
 
 from dateutil.relativedelta import relativedelta
 from discord import Colour, Embed, Message
-from discord.ext.commands import Bot, Cog, Context, group
+from discord.ext.commands import Cog, Context, group
 
+from bot.bot import Bot
 from bot.constants import Channels, Icons, NEGATIVE_REPLIES, POSITIVE_REPLIES, STAFF_ROLES
 from bot.converters import Duration
 from bot.pagination import LinePaginator
@@ -104,7 +105,10 @@ class Reminders(Scheduler, Cog):
             name="It has arrived!"
         )
 
-        embed.description = f"Here's your reminder: `{reminder['content']}`"
+        embed.description = f"Here's your reminder: `{reminder['content']}`."
+
+        if reminder.get("jump_url"):  # keep backward compatibility
+            embed.description += f"\n[Jump back to when you created the reminder]({reminder['jump_url']})"
 
         if late:
             embed.colour = Colour.red()
@@ -167,14 +171,18 @@ class Reminders(Scheduler, Cog):
             json={
                 'author': ctx.author.id,
                 'channel_id': ctx.message.channel.id,
+                'jump_url': ctx.message.jump_url,
                 'content': content,
                 'expiration': expiration.isoformat()
             }
         )
 
+        now = datetime.utcnow() - timedelta(seconds=1)
+
         # Confirm to the user that it worked.
         await self._send_confirmation(
-            ctx, on_success="Your reminder has been created successfully!"
+            ctx,
+            on_success=f"Your reminder will arrive in {humanize_delta(relativedelta(expiration, now))}!"
         )
 
         loop = asyncio.get_event_loop()
@@ -283,6 +291,5 @@ class Reminders(Scheduler, Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Reminders cog load."""
+    """Load the Reminders cog."""
     bot.add_cog(Reminders(bot))
-    log.info("Cog loaded: Reminders")
diff --git a/bot/cogs/security.py b/bot/cogs/security.py
index 316b33d6b..c680c5e27 100644
--- a/bot/cogs/security.py
+++ b/bot/cogs/security.py
@@ -1,6 +1,8 @@
 import logging
 
-from discord.ext.commands import Bot, Cog, Context, NoPrivateMessage
+from discord.ext.commands import Cog, Context, NoPrivateMessage
+
+from bot.bot import Bot
 
 log = logging.getLogger(__name__)
 
@@ -25,6 +27,5 @@ class Security(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Security cog load."""
+    """Load the Security cog."""
     bot.add_cog(Security(bot))
-    log.info("Cog loaded: Security")
diff --git a/bot/cogs/site.py b/bot/cogs/site.py
index c3bdf85e4..853e29568 100644
--- a/bot/cogs/site.py
+++ b/bot/cogs/site.py
@@ -1,10 +1,10 @@
 import logging
 
 from discord import Colour, Embed
-from discord.ext.commands import Bot, Cog, Context, group
+from discord.ext.commands import Cog, Context, group
 
-from bot.constants import Channels, STAFF_ROLES, URLs
-from bot.decorators import redirect_output
+from bot.bot import Bot
+from bot.constants import URLs
 from bot.pagination import LinePaginator
 
 log = logging.getLogger(__name__)
@@ -59,7 +59,7 @@ class Site(Cog):
     @site_group.command(name="tools")
     async def site_tools(self, ctx: Context) -> None:
         """Info about the site's Tools page."""
-        tools_url = f"{PAGES_URL}/tools"
+        tools_url = f"{PAGES_URL}/resources/tools"
 
         embed = Embed(title="Tools")
         embed.set_footer(text=f"{tools_url}")
@@ -74,7 +74,7 @@ class Site(Cog):
     @site_group.command(name="help")
     async def site_help(self, ctx: Context) -> None:
         """Info about the site's Getting Help page."""
-        url = f"{PAGES_URL}/asking-good-questions"
+        url = f"{PAGES_URL}/resources/guides/asking-good-questions"
 
         embed = Embed(title="Asking Good Questions")
         embed.set_footer(text=url)
@@ -105,7 +105,6 @@ class Site(Cog):
         await ctx.send(embed=embed)
 
     @site_group.command(aliases=['r', 'rule'], name='rules')
-    @redirect_output(destination_channel=Channels.bot, bypass_roles=STAFF_ROLES)
     async def site_rules(self, ctx: Context, *rules: int) -> None:
         """Provides a link to all rules or, if specified, displays specific rule(s)."""
         rules_embed = Embed(title='Rules', color=Colour.blurple())
@@ -126,20 +125,19 @@ class Site(Cog):
         invalid_indices = tuple(
             pick
             for pick in rules
-            if pick < 0 or pick >= len(full_rules)
+            if pick < 1 or pick > len(full_rules)
         )
 
         if invalid_indices:
             indices = ', '.join(map(str, invalid_indices))
-            await ctx.send(f":x: Invalid rule indices {indices}")
+            await ctx.send(f":x: Invalid rule indices: {indices}")
             return
 
-        final_rules = tuple(f"**{pick}.** {full_rules[pick]}" for pick in rules)
+        final_rules = tuple(f"**{pick}.** {full_rules[pick - 1]}" for pick in rules)
 
         await LinePaginator.paginate(final_rules, ctx, rules_embed, max_lines=3)
 
 
 def setup(bot: Bot) -> None:
-    """Site cog load."""
+    """Load the Site cog."""
     bot.add_cog(Site(bot))
-    log.info("Cog loaded: Site")
diff --git a/bot/cogs/snekbox.py b/bot/cogs/snekbox.py
index 81185cf3e..da33e27b2 100644
--- a/bot/cogs/snekbox.py
+++ b/bot/cogs/snekbox.py
@@ -5,8 +5,9 @@ import textwrap
 from signal import Signals
 from typing import Optional, Tuple
 
-from discord.ext.commands import Bot, Cog, Context, command, guild_only
+from discord.ext.commands import Cog, Context, command, guild_only
 
+from bot.bot import Bot
 from bot.constants import Channels, Roles, URLs
 from bot.decorators import in_channel
 from bot.utils.messages import wait_for_deletion
@@ -115,6 +116,16 @@ class Snekbox(Cog):
 
         return msg, error
 
+    @staticmethod
+    def get_status_emoji(results: dict) -> str:
+        """Return an emoji corresponding to the status code or lack of output in result."""
+        if not results["stdout"].strip():  # No output
+            return ":warning:"
+        elif results["returncode"] == 0:  # No error
+            return ":white_check_mark:"
+        else:  # Exception
+            return ":x:"
+
     async def format_output(self, output: str) -> Tuple[str, Optional[str]]:
         """
         Format the output and return a tuple of the formatted output and a URL to the full output.
@@ -166,7 +177,7 @@ class Snekbox(Cog):
 
     @command(name="eval", aliases=("e",))
     @guild_only()
-    @in_channel(Channels.bot, bypass_roles=EVAL_ROLES)
+    @in_channel(Channels.bot, hidden_channels=(Channels.esoteric,), bypass_roles=EVAL_ROLES)
     async def eval_command(self, ctx: Context, *, code: str = None) -> None:
         """
         Run Python code and get the results.
@@ -178,7 +189,7 @@ class Snekbox(Cog):
         if ctx.author.id in self.jobs:
             await ctx.send(
                 f"{ctx.author.mention} You've already got a job running - "
-                f"please wait for it to finish!"
+                "please wait for it to finish!"
             )
             return
 
@@ -186,10 +197,7 @@ class Snekbox(Cog):
             await ctx.invoke(self.bot.get_command("help"), "eval")
             return
 
-        log.info(
-            f"Received code from {ctx.author.name}#{ctx.author.discriminator} "
-            f"for evaluation:\n{code}"
-        )
+        log.info(f"Received code from {ctx.author} for evaluation:\n{code}")
 
         self.jobs[ctx.author.id] = datetime.datetime.now()
         code = self.prepare_input(code)
@@ -204,7 +212,8 @@ class Snekbox(Cog):
                 else:
                     output, paste_link = await self.format_output(results["stdout"])
 
-                msg = f"{ctx.author.mention} {msg}.\n\n```py\n{output}\n```"
+                icon = self.get_status_emoji(results)
+                msg = f"{ctx.author.mention} {icon} {msg}.\n\n```py\n{output}\n```"
                 if paste_link:
                     msg = f"{msg}\nFull output: {paste_link}"
 
@@ -213,15 +222,11 @@ class Snekbox(Cog):
                     wait_for_deletion(response, user_ids=(ctx.author.id,), client=ctx.bot)
                 )
 
-                log.info(
-                    f"{ctx.author.name}#{ctx.author.discriminator}'s job had a return code of "
-                    f"{results['returncode']}"
-                )
+                log.info(f"{ctx.author}'s job had a return code of {results['returncode']}")
         finally:
             del self.jobs[ctx.author.id]
 
 
 def setup(bot: Bot) -> None:
-    """Snekbox cog load."""
+    """Load the Snekbox cog."""
     bot.add_cog(Snekbox(bot))
-    log.info("Cog loaded: Snekbox")
diff --git a/bot/cogs/sync/__init__.py b/bot/cogs/sync/__init__.py
index d4565f848..fe7df4e9b 100644
--- a/bot/cogs/sync/__init__.py
+++ b/bot/cogs/sync/__init__.py
@@ -1,13 +1,7 @@
-import logging
-
-from discord.ext.commands import Bot
-
+from bot.bot import Bot
 from .cog import Sync
 
-log = logging.getLogger(__name__)
-
 
 def setup(bot: Bot) -> None:
-    """Sync cog load."""
+    """Load the Sync cog."""
     bot.add_cog(Sync(bot))
-    log.info("Cog loaded: Sync")
diff --git a/bot/cogs/sync/cog.py b/bot/cogs/sync/cog.py
index aaa581f96..4e6ed156b 100644
--- a/bot/cogs/sync/cog.py
+++ b/bot/cogs/sync/cog.py
@@ -1,12 +1,13 @@
 import logging
-from typing import Callable, Iterable
+from typing import Callable, Dict, Iterable, Union
 
-from discord import Guild, Member, Role
+from discord import Guild, Member, Role, User
 from discord.ext import commands
-from discord.ext.commands import Bot, Cog, Context
+from discord.ext.commands import Cog, Context
 
 from bot import constants
 from bot.api import ResponseCodeError
+from bot.bot import Bot
 from bot.cogs.sync import syncers
 
 log = logging.getLogger(__name__)
@@ -50,6 +51,15 @@ class Sync(Cog):
                         f"deleted `{total_deleted}`."
                     )
 
+    async def patch_user(self, user_id: int, updated_information: Dict[str, Union[str, int]]) -> None:
+        """Send a PATCH request to partially update a user in the database."""
+        try:
+            await self.bot.api_client.patch("bot/users/" + str(user_id), json=updated_information)
+        except ResponseCodeError as e:
+            if e.response.status != 404:
+                raise
+            log.warning("Unable to update user, got 404. Assuming race condition from join event.")
+
     @Cog.listener()
     async def on_guild_role_create(self, role: Role) -> None:
         """Adds newly create role to the database table over the API."""
@@ -142,33 +152,21 @@ class Sync(Cog):
 
     @Cog.listener()
     async def on_member_update(self, before: Member, after: Member) -> None:
-        """Updates the user information if any of relevant attributes have changed."""
-        if (
-                before.name != after.name
-                or before.avatar != after.avatar
-                or before.discriminator != after.discriminator
-                or before.roles != after.roles
-        ):
-            try:
-                await self.bot.api_client.put(
-                    'bot/users/' + str(after.id),
-                    json={
-                        'avatar_hash': after.avatar,
-                        'discriminator': int(after.discriminator),
-                        'id': after.id,
-                        'in_guild': True,
-                        'name': after.name,
-                        'roles': sorted(role.id for role in after.roles)
-                    }
-                )
-            except ResponseCodeError as e:
-                if e.response.status != 404:
-                    raise
-
-                log.warning(
-                    "Unable to update user, got 404. "
-                    "Assuming race condition from join event."
-                )
+        """Update the roles of the member in the database if a change is detected."""
+        if before.roles != after.roles:
+            updated_information = {"roles": sorted(role.id for role in after.roles)}
+            await self.patch_user(after.id, updated_information=updated_information)
+
+    @Cog.listener()
+    async def on_user_update(self, before: User, after: User) -> None:
+        """Update the user information in the database if a relevant change is detected."""
+        if any(getattr(before, attr) != getattr(after, attr) for attr in ("name", "discriminator", "avatar")):
+            updated_information = {
+                "name": after.name,
+                "discriminator": int(after.discriminator),
+                "avatar_hash": after.avatar,
+            }
+            await self.patch_user(after.id, updated_information=updated_information)
 
     @commands.group(name='sync')
     @commands.has_permissions(administrator=True)
diff --git a/bot/cogs/sync/syncers.py b/bot/cogs/sync/syncers.py
index 2cc5a66e1..14cf51383 100644
--- a/bot/cogs/sync/syncers.py
+++ b/bot/cogs/sync/syncers.py
@@ -2,7 +2,8 @@ from collections import namedtuple
 from typing import Dict, Set, Tuple
 
 from discord import Guild
-from discord.ext.commands import Bot
+
+from bot.bot import Bot
 
 # These objects are declared as namedtuples because tuples are hashable,
 # something that we make use of when diffing site roles against guild roles.
@@ -52,7 +53,7 @@ async def sync_roles(bot: Bot, guild: Guild) -> Tuple[int, int, int]:
     Synchronize roles found on the given `guild` with the ones on the API.
 
     Arguments:
-        bot (discord.ext.commands.Bot):
+        bot (bot.bot.Bot):
             The bot instance that we're running with.
 
         guild (discord.Guild):
@@ -169,7 +170,7 @@ async def sync_users(bot: Bot, guild: Guild) -> Tuple[int, int, None]:
     Synchronize users found in the given `guild` with the ones in the API.
 
     Arguments:
-        bot (discord.ext.commands.Bot):
+        bot (bot.bot.Bot):
             The bot instance that we're running with.
 
         guild (discord.Guild):
diff --git a/bot/cogs/tags.py b/bot/cogs/tags.py
index cd70e783a..54a51921c 100644
--- a/bot/cogs/tags.py
+++ b/bot/cogs/tags.py
@@ -1,15 +1,17 @@
 import logging
+import re
 import time
+from typing import Dict, List, Optional
 
 from discord import Colour, Embed
-from discord.ext.commands import Bot, Cog, Context, group
+from discord.ext.commands import Cog, Context, group
 
+from bot.bot import Bot
 from bot.constants import Channels, Cooldowns, MODERATION_ROLES, Roles
 from bot.converters import TagContentConverter, TagNameConverter
 from bot.decorators import with_role
 from bot.pagination import LinePaginator
 
-
 log = logging.getLogger(__name__)
 
 TEST_CHANNELS = (
@@ -18,6 +20,8 @@ TEST_CHANNELS = (
     Channels.helpers
 )
 
+REGEX_NON_ALPHABET = re.compile(r"[^a-z]", re.MULTILINE & re.IGNORECASE)
+
 
 class Tags(Cog):
     """Save new tags and fetch existing tags."""
@@ -26,6 +30,63 @@ class Tags(Cog):
         self.bot = bot
         self.tag_cooldowns = {}
 
+        self._cache = {}
+        self._last_fetch: float = 0.0
+
+    async def _get_tags(self, is_forced: bool = False) -> None:
+        """Get all tags."""
+        # refresh only when there's a more than 5m gap from last call.
+        time_now: float = time.time()
+        if is_forced or not self._last_fetch or time_now - self._last_fetch > 5 * 60:
+            tags = await self.bot.api_client.get('bot/tags')
+            self._cache = {tag['title'].lower(): tag for tag in tags}
+            self._last_fetch = time_now
+
+    @staticmethod
+    def _fuzzy_search(search: str, target: str) -> int:
+        """A simple scoring algorithm based on how many letters are found / total, with order in mind."""
+        current, index = 0, 0
+        _search = REGEX_NON_ALPHABET.sub('', search.lower())
+        _targets = iter(REGEX_NON_ALPHABET.split(target.lower()))
+        _target = next(_targets)
+        try:
+            while True:
+                while index < len(_target) and _search[current] == _target[index]:
+                    current += 1
+                    index += 1
+                index, _target = 0, next(_targets)
+        except (StopIteration, IndexError):
+            pass
+        return current / len(_search) * 100
+
+    def _get_suggestions(self, tag_name: str, thresholds: Optional[List[int]] = None) -> List[str]:
+        """Return a list of suggested tags."""
+        scores: Dict[str, int] = {
+            tag_title: Tags._fuzzy_search(tag_name, tag['title'])
+            for tag_title, tag in self._cache.items()
+        }
+
+        thresholds = thresholds or [100, 90, 80, 70, 60]
+
+        for threshold in thresholds:
+            suggestions = [
+                self._cache[tag_title]
+                for tag_title, matching_score in scores.items()
+                if matching_score >= threshold
+            ]
+            if suggestions:
+                return suggestions
+
+        return []
+
+    async def _get_tag(self, tag_name: str) -> list:
+        """Get a specific tag."""
+        await self._get_tags()
+        found = [self._cache.get(tag_name.lower(), None)]
+        if not found[0]:
+            return self._get_suggestions(tag_name)
+        return found
+
     @group(name='tags', aliases=('tag', 't'), invoke_without_command=True)
     async def tags_group(self, ctx: Context, *, tag_name: TagNameConverter = None) -> None:
         """Show all known tags, a single tag, or run a subcommand."""
@@ -59,17 +120,27 @@ class Tags(Cog):
                         f"Cooldown ends in {time_left:.1f} seconds.")
             return
 
+        await self._get_tags()
+
         if tag_name is not None:
-            tag = await self.bot.api_client.get(f'bot/tags/{tag_name}')
-            if ctx.channel.id not in TEST_CHANNELS:
-                self.tag_cooldowns[tag_name] = {
-                    "time": time.time(),
-                    "channel": ctx.channel.id
-                }
-            await ctx.send(embed=Embed.from_dict(tag['embed']))
+            founds = await self._get_tag(tag_name)
+
+            if len(founds) == 1:
+                tag = founds[0]
+                if ctx.channel.id not in TEST_CHANNELS:
+                    self.tag_cooldowns[tag_name] = {
+                        "time": time.time(),
+                        "channel": ctx.channel.id
+                    }
+                await ctx.send(embed=Embed.from_dict(tag['embed']))
+            elif founds and len(tag_name) >= 3:
+                await ctx.send(embed=Embed(
+                    title='Did you mean ...',
+                    description='\n'.join(tag['title'] for tag in founds[:10])
+                ))
 
         else:
-            tags = await self.bot.api_client.get('bot/tags')
+            tags = self._cache.values()
             if not tags:
                 await ctx.send(embed=Embed(
                     description="**There are no tags in the database!**",
@@ -105,6 +176,7 @@ class Tags(Cog):
         }
 
         await self.bot.api_client.post('bot/tags', json=body)
+        self._cache[tag_name.lower()] = await self.bot.api_client.get(f'bot/tags/{tag_name}')
 
         log.debug(f"{ctx.author} successfully added the following tag to our database: \n"
                   f"tag_name: {tag_name}\n"
@@ -134,6 +206,7 @@ class Tags(Cog):
         }
 
         await self.bot.api_client.patch(f'bot/tags/{tag_name}', json=body)
+        self._cache[tag_name.lower()] = await self.bot.api_client.get(f'bot/tags/{tag_name}')
 
         log.debug(f"{ctx.author} successfully edited the following tag in our database: \n"
                   f"tag_name: {tag_name}\n"
@@ -150,6 +223,7 @@ class Tags(Cog):
     async def delete_command(self, ctx: Context, *, tag_name: TagNameConverter) -> None:
         """Remove a tag from the database."""
         await self.bot.api_client.delete(f'bot/tags/{tag_name}')
+        self._cache.pop(tag_name.lower(), None)
 
         log.debug(f"{ctx.author} successfully deleted the tag called '{tag_name}'")
         await ctx.send(embed=Embed(
@@ -160,6 +234,5 @@ class Tags(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Tags cog load."""
+    """Load the Tags cog."""
     bot.add_cog(Tags(bot))
-    log.info("Cog loaded: Tags")
diff --git a/bot/cogs/token_remover.py b/bot/cogs/token_remover.py
index 5a0d20e57..82c01ae96 100644
--- a/bot/cogs/token_remover.py
+++ b/bot/cogs/token_remover.py
@@ -6,9 +6,10 @@ import struct
 from datetime import datetime
 
 from discord import Colour, Message
-from discord.ext.commands import Bot, Cog
+from discord.ext.commands import Cog
 from discord.utils import snowflake_time
 
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
 from bot.constants import Channels, Colours, Event, Icons
 
@@ -52,39 +53,60 @@ class TokenRemover(Cog):
 
         See: https://discordapp.com/developers/docs/reference#snowflakes
         """
+        if self.is_token_in_message(msg):
+            await self.take_action(msg)
+
+    @Cog.listener()
+    async def on_message_edit(self, before: Message, after: Message) -> None:
+        """
+        Check each edit for a string that matches Discord's token pattern.
+
+        See: https://discordapp.com/developers/docs/reference#snowflakes
+        """
+        if self.is_token_in_message(after):
+            await self.take_action(after)
+
+    async def take_action(self, msg: Message) -> None:
+        """Remove the `msg` containing a token an send a mod_log message."""
+        user_id, creation_timestamp, hmac = TOKEN_RE.search(msg.content).group(0).split('.')
+        self.mod_log.ignore(Event.message_delete, msg.id)
+        await msg.delete()
+        await msg.channel.send(DELETION_MESSAGE_TEMPLATE.format(mention=msg.author.mention))
+
+        message = (
+            "Censored a seemingly valid token sent by "
+            f"{msg.author} (`{msg.author.id}`) in {msg.channel.mention}, token was "
+            f"`{user_id}.{creation_timestamp}.{'x' * len(hmac)}`"
+        )
+        log.debug(message)
+
+        # Send pretty mod log embed to mod-alerts
+        await self.mod_log.send_log_message(
+            icon_url=Icons.token_removed,
+            colour=Colour(Colours.soft_red),
+            title="Token removed!",
+            text=message,
+            thumbnail=msg.author.avatar_url_as(static_format="png"),
+            channel_id=Channels.mod_alerts,
+        )
+
+    @classmethod
+    def is_token_in_message(cls, msg: Message) -> bool:
+        """Check if `msg` contains a seemly valid token."""
         if msg.author.bot:
-            return
+            return False
 
         maybe_match = TOKEN_RE.search(msg.content)
         if maybe_match is None:
-            return
+            return False
 
         try:
             user_id, creation_timestamp, hmac = maybe_match.group(0).split('.')
         except ValueError:
-            return
-
-        if self.is_valid_user_id(user_id) and self.is_valid_timestamp(creation_timestamp):
-            self.mod_log.ignore(Event.message_delete, msg.id)
-            await msg.delete()
-            await msg.channel.send(DELETION_MESSAGE_TEMPLATE.format(mention=msg.author.mention))
-
-            message = (
-                "Censored a seemingly valid token sent by "
-                f"{msg.author} (`{msg.author.id}`) in {msg.channel.mention}, token was "
-                f"`{user_id}.{creation_timestamp}.{'x' * len(hmac)}`"
-            )
-            log.debug(message)
-
-            # Send pretty mod log embed to mod-alerts
-            await self.mod_log.send_log_message(
-                icon_url=Icons.token_removed,
-                colour=Colour(Colours.soft_red),
-                title="Token removed!",
-                text=message,
-                thumbnail=msg.author.avatar_url_as(static_format="png"),
-                channel_id=Channels.mod_alerts,
-            )
+            return False
+
+        if cls.is_valid_user_id(user_id) and cls.is_valid_timestamp(creation_timestamp):
+            return True
 
     @staticmethod
     def is_valid_user_id(b64_content: str) -> bool:
@@ -119,6 +141,5 @@ class TokenRemover(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Token Remover cog load."""
+    """Load the TokenRemover cog."""
     bot.add_cog(TokenRemover(bot))
-    log.info("Cog loaded: TokenRemover")
diff --git a/bot/cogs/utils.py b/bot/cogs/utils.py
index b6cecdc7c..da278011a 100644
--- a/bot/cogs/utils.py
+++ b/bot/cogs/utils.py
@@ -1,15 +1,19 @@
 import logging
 import re
 import unicodedata
+from asyncio import TimeoutError, sleep
 from email.parser import HeaderParser
 from io import StringIO
 from typing import Tuple
 
-from discord import Colour, Embed
-from discord.ext.commands import Bot, Cog, Context, command
+from dateutil import relativedelta
+from discord import Colour, Embed, Message, Role
+from discord.ext.commands import Cog, Context, command
 
-from bot.constants import Channels, STAFF_ROLES
-from bot.decorators import in_channel
+from bot.bot import Bot
+from bot.constants import Channels, MODERATION_ROLES, Mention, STAFF_ROLES
+from bot.decorators import in_channel, with_role
+from bot.utils.time import humanize_delta
 
 log = logging.getLogger(__name__)
 
@@ -32,56 +36,56 @@ class Utils(Cog):
             await ctx.invoke(self.bot.get_command("help"), "pep")
             return
 
-        # Newer PEPs are written in RST instead of txt
-        if pep_number > 542:
-            pep_url = f"{self.base_github_pep_url}{pep_number:04}.rst"
-        else:
-            pep_url = f"{self.base_github_pep_url}{pep_number:04}.txt"
+        possible_extensions = ['.txt', '.rst']
+        found_pep = False
+        for extension in possible_extensions:
+            # Attempt to fetch the PEP
+            pep_url = f"{self.base_github_pep_url}{pep_number:04}{extension}"
+            log.trace(f"Requesting PEP {pep_number} with {pep_url}")
+            response = await self.bot.http_session.get(pep_url)
 
-        # Attempt to fetch the PEP
-        log.trace(f"Requesting PEP {pep_number} with {pep_url}")
-        response = await self.bot.http_session.get(pep_url)
+            if response.status == 200:
+                log.trace("PEP found")
+                found_pep = True
 
-        if response.status == 200:
-            log.trace("PEP found")
+                pep_content = await response.text()
 
-            pep_content = await response.text()
+                # Taken from https://github.com/python/peps/blob/master/pep0/pep.py#L179
+                pep_header = HeaderParser().parse(StringIO(pep_content))
 
-            # Taken from https://github.com/python/peps/blob/master/pep0/pep.py#L179
-            pep_header = HeaderParser().parse(StringIO(pep_content))
+                # Assemble the embed
+                pep_embed = Embed(
+                    title=f"**PEP {pep_number} - {pep_header['Title']}**",
+                    description=f"[Link]({self.base_pep_url}{pep_number:04})",
+                )
 
-            # Assemble the embed
-            pep_embed = Embed(
-                title=f"**PEP {pep_number} - {pep_header['Title']}**",
-                description=f"[Link]({self.base_pep_url}{pep_number:04})",
-            )
+                pep_embed.set_thumbnail(url="https://www.python.org/static/opengraph-icon-200x200.png")
 
-            pep_embed.set_thumbnail(url="https://www.python.org/static/opengraph-icon-200x200.png")
+                # Add the interesting information
+                fields_to_check = ("Status", "Python-Version", "Created", "Type")
+                for field in fields_to_check:
+                    # Check for a PEP metadata field that is present but has an empty value
+                    # embed field values can't contain an empty string
+                    if pep_header.get(field, ""):
+                        pep_embed.add_field(name=field, value=pep_header[field])
 
-            # Add the interesting information
-            if "Status" in pep_header:
-                pep_embed.add_field(name="Status", value=pep_header["Status"])
-            if "Python-Version" in pep_header:
-                pep_embed.add_field(name="Python-Version", value=pep_header["Python-Version"])
-            if "Created" in pep_header:
-                pep_embed.add_field(name="Created", value=pep_header["Created"])
-            if "Type" in pep_header:
-                pep_embed.add_field(name="Type", value=pep_header["Type"])
+            elif response.status != 404:
+                # any response except 200 and 404 is expected
+                found_pep = True  # actually not, but it's easier to display this way
+                log.trace(f"The user requested PEP {pep_number}, but the response had an unexpected status code: "
+                          f"{response.status}.\n{response.text}")
 
-        elif response.status == 404:
+                error_message = "Unexpected HTTP error during PEP search. Please let us know."
+                pep_embed = Embed(title="Unexpected error", description=error_message)
+                pep_embed.colour = Colour.red()
+                break
+
+        if not found_pep:
             log.trace("PEP was not found")
             not_found = f"PEP {pep_number} does not exist."
             pep_embed = Embed(title="PEP not found", description=not_found)
             pep_embed.colour = Colour.red()
 
-        else:
-            log.trace(f"The user requested PEP {pep_number}, but the response had an unexpected status code: "
-                      f"{response.status}.\n{response.text}")
-
-            error_message = "Unexpected HTTP error during PEP search. Please let us know."
-            pep_embed = Embed(title="Unexpected error", description=error_message)
-            pep_embed.colour = Colour.red()
-
         await ctx.message.channel.send(embed=pep_embed)
 
     @command()
@@ -128,8 +132,48 @@ class Utils(Cog):
 
         await ctx.send(embed=embed)
 
+    @command()
+    @with_role(*MODERATION_ROLES)
+    async def mention(self, ctx: Context, *, role: Role) -> None:
+        """Set a role to be mentionable for a limited time."""
+        if role.mentionable:
+            await ctx.send(f"{role} is already mentionable!")
+            return
+
+        await role.edit(reason=f"Role unlocked by {ctx.author}", mentionable=True)
+
+        human_time = humanize_delta(relativedelta.relativedelta(seconds=Mention.message_timeout))
+        await ctx.send(
+            f"{role} has been made mentionable. I will reset it in {human_time}, or when someone mentions this role."
+        )
+
+        def check(m: Message) -> bool:
+            """Checks that the message contains the role mention."""
+            return role in m.role_mentions
+
+        try:
+            msg = await self.bot.wait_for("message", check=check, timeout=Mention.message_timeout)
+        except TimeoutError:
+            await role.edit(mentionable=False, reason="Automatic role lock - timeout.")
+            await ctx.send(f"{ctx.author.mention}, you took too long. I have reset {role} to be unmentionable.")
+            return
+
+        if any(r.id in MODERATION_ROLES for r in msg.author.roles):
+            await sleep(Mention.reset_delay)
+            await role.edit(mentionable=False, reason=f"Automatic role lock by {msg.author}")
+            await ctx.send(
+                f"{ctx.author.mention}, I have reset {role} to be unmentionable as "
+                f"{msg.author if msg.author != ctx.author else 'you'} sent a message mentioning it."
+            )
+            return
+
+        await role.edit(mentionable=False, reason=f"Automatic role lock - unauthorised use by {msg.author}")
+        await ctx.send(
+            f"{ctx.author.mention}, I have reset {role} to be unmentionable "
+            f"as I detected unauthorised use by {msg.author} (ID: {msg.author.id})."
+        )
+
 
 def setup(bot: Bot) -> None:
-    """Utils cog load."""
+    """Load the Utils cog."""
     bot.add_cog(Utils(bot))
-    log.info("Cog loaded: Utils")
diff --git a/bot/cogs/verification.py b/bot/cogs/verification.py
index 5b115deaa..988e0d49a 100644
--- a/bot/cogs/verification.py
+++ b/bot/cogs/verification.py
@@ -1,13 +1,19 @@
 import logging
 from datetime import datetime
 
-from discord import Message, NotFound, Object
+from discord import Colour, Message, NotFound, Object
 from discord.ext import tasks
-from discord.ext.commands import Bot, Cog, Context, command
+from discord.ext.commands import Cog, Context, command
 
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
-from bot.constants import Bot as BotConfig, Channels, Event, Roles
+from bot.constants import (
+    Bot as BotConfig,
+    Channels, Colours, Event,
+    Filter, Icons, MODERATION_ROLES, Roles
+)
 from bot.decorators import InChannelCheckFailure, in_channel, without_role
+from bot.utils.checks import without_role_check
 
 log = logging.getLogger(__name__)
 
@@ -31,8 +37,9 @@ If you'd like to unsubscribe from the announcement notifications, simply send `!
 
 PERIODIC_PING = (
     f"@everyone To verify that you have read our rules, please type `{BotConfig.prefix}accept`."
-    f" Ping <@&{Roles.admin}> if you encounter any problems during the verification process."
+    f" If you encounter any problems during the verification process, ping the <@&{Roles.admin}> role in this channel."
 )
+BOT_MESSAGE_DELETE_DELAY = 10
 
 
 class Verification(Cog):
@@ -50,35 +57,66 @@ class Verification(Cog):
     @Cog.listener()
     async def on_message(self, message: Message) -> None:
         """Check new message event for messages to the checkpoint channel & process."""
+        if message.channel.id != Channels.verification:
+            return  # Only listen for #checkpoint messages
+
         if message.author.bot:
-            return  # They're a bot, ignore
+            # They're a bot, delete their message after the delay.
+            # But not the periodic ping; we like that one.
+            if message.content != PERIODIC_PING:
+                await message.delete(delay=BOT_MESSAGE_DELETE_DELAY)
+            return
+
+        # if a user mentions a role or guild member
+        # alert the mods in mod-alerts channel
+        if message.mentions or message.role_mentions:
+            log.debug(
+                f"{message.author} mentioned one or more users "
+                f"and/or roles in {message.channel.name}"
+            )
+
+            embed_text = (
+                f"{message.author.mention} sent a message in "
+                f"{message.channel.mention} that contained user and/or role mentions."
+                f"\n\n**Original message:**\n>>> {message.content}"
+            )
+
+            # Send pretty mod log embed to mod-alerts
+            await self.mod_log.send_log_message(
+                icon_url=Icons.filtering,
+                colour=Colour(Colours.soft_red),
+                title=f"User/Role mentioned in {message.channel.name}",
+                text=embed_text,
+                thumbnail=message.author.avatar_url_as(static_format="png"),
+                channel_id=Channels.mod_alerts,
+                ping_everyone=Filter.ping_everyone,
+            )
 
         ctx = await self.bot.get_context(message)  # type: Context
 
         if ctx.command is not None and ctx.command.name == "accept":
             return  # They used the accept command
 
-        if ctx.channel.id == Channels.verification:  # We're in the verification channel
-            for role in ctx.author.roles:
-                if role.id == Roles.verified:
-                    log.warning(f"{ctx.author} posted '{ctx.message.content}' "
-                                "in the verification channel, but is already verified.")
-                    return  # They're already verified
-
-            log.debug(f"{ctx.author} posted '{ctx.message.content}' in the verification "
-                      "channel. We are providing instructions how to verify.")
-            await ctx.send(
-                f"{ctx.author.mention} Please type `!accept` to verify that you accept our rules, "
-                f"and gain access to the rest of the server.",
-                delete_after=20
-            )
+        for role in ctx.author.roles:
+            if role.id == Roles.verified:
+                log.warning(f"{ctx.author} posted '{ctx.message.content}' "
+                            "in the verification channel, but is already verified.")
+                return  # They're already verified
+
+        log.debug(f"{ctx.author} posted '{ctx.message.content}' in the verification "
+                  "channel. We are providing instructions how to verify.")
+        await ctx.send(
+            f"{ctx.author.mention} Please type `!accept` to verify that you accept our rules, "
+            f"and gain access to the rest of the server.",
+            delete_after=20
+        )
 
-            log.trace(f"Deleting the message posted by {ctx.author}")
+        log.trace(f"Deleting the message posted by {ctx.author}")
 
-            try:
-                await ctx.message.delete()
-            except NotFound:
-                log.trace("No message found, it must have been deleted by another bot.")
+        try:
+            await ctx.message.delete()
+        except NotFound:
+            log.trace("No message found, it must have been deleted by another bot.")
 
     @command(name='accept', aliases=('verify', 'verified', 'accepted'), hidden=True)
     @without_role(Roles.verified)
@@ -158,7 +196,7 @@ class Verification(Cog):
     @staticmethod
     def bot_check(ctx: Context) -> bool:
         """Block any command within the verification channel that is not !accept."""
-        if ctx.channel.id == Channels.verification:
+        if ctx.channel.id == Channels.verification and without_role_check(ctx, *MODERATION_ROLES):
             return ctx.command.name == "accept"
         else:
             return True
@@ -193,6 +231,5 @@ class Verification(Cog):
 
 
 def setup(bot: Bot) -> None:
-    """Verification cog load."""
+    """Load the Verification cog."""
     bot.add_cog(Verification(bot))
-    log.info("Cog loaded: Verification")
diff --git a/bot/cogs/watchchannels/__init__.py b/bot/cogs/watchchannels/__init__.py
index 86e1050fa..69d118df6 100644
--- a/bot/cogs/watchchannels/__init__.py
+++ b/bot/cogs/watchchannels/__init__.py
@@ -1,18 +1,9 @@
-import logging
-
-from discord.ext.commands import Bot
-
+from bot.bot import Bot
 from .bigbrother import BigBrother
 from .talentpool import TalentPool
 
 
-log = logging.getLogger(__name__)
-
-
 def setup(bot: Bot) -> None:
-    """Monitoring cogs load."""
+    """Load the BigBrother and TalentPool cogs."""
     bot.add_cog(BigBrother(bot))
-    log.info("Cog loaded: BigBrother")
-
     bot.add_cog(TalentPool(bot))
-    log.info("Cog loaded: TalentPool")
diff --git a/bot/cogs/watchchannels/bigbrother.py b/bot/cogs/watchchannels/bigbrother.py
index c516508ca..c601e0d4d 100644
--- a/bot/cogs/watchchannels/bigbrother.py
+++ b/bot/cogs/watchchannels/bigbrother.py
@@ -1,14 +1,14 @@
 import logging
 from collections import ChainMap
-from typing import Union
 
-from discord import User
-from discord.ext.commands import Bot, Cog, Context, group
+from discord.ext.commands import Cog, Context, group
 
+from bot.bot import Bot
 from bot.cogs.moderation.utils import post_infraction
-from bot.constants import Channels, Roles, Webhooks
+from bot.constants import Channels, MODERATION_ROLES, Webhooks
+from bot.converters import FetchedMember
 from bot.decorators import with_role
-from .watchchannel import WatchChannel, proxy_user
+from .watchchannel import WatchChannel
 
 log = logging.getLogger(__name__)
 
@@ -27,13 +27,13 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         )
 
     @group(name='bigbrother', aliases=('bb',), invoke_without_command=True)
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
+    @with_role(*MODERATION_ROLES)
     async def bigbrother_group(self, ctx: Context) -> None:
         """Monitors users by relaying their messages to the Big Brother watch channel."""
         await ctx.invoke(self.bot.get_command("help"), "bigbrother")
 
     @bigbrother_group.command(name='watched', aliases=('all', 'list'))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
+    @with_role(*MODERATION_ROLES)
     async def watched_command(self, ctx: Context, update_cache: bool = True) -> None:
         """
         Shows the users that are currently being monitored by Big Brother.
@@ -44,8 +44,8 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         await self.list_watched_users(ctx, update_cache)
 
     @bigbrother_group.command(name='watch', aliases=('w',))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
-    async def watch_command(self, ctx: Context, user: Union[User, proxy_user], *, reason: str) -> None:
+    @with_role(*MODERATION_ROLES)
+    async def watch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """
         Relay messages sent by the given `user` to the `#big-brother` channel.
 
@@ -61,10 +61,10 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
             return
 
         if user.id in self.watched_users:
-            await ctx.send(":x: The specified user is already being watched.")
+            await ctx.send(f":x: {user} is already being watched.")
             return
 
-        response = await post_infraction(ctx, user, 'watch', reason, hidden=True)
+        response = await post_infraction(ctx, user, 'watch', reason, hidden=True, active=True)
 
         if response is not None:
             self.watched_users[user.id] = response
@@ -91,8 +91,8 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         await ctx.send(msg)
 
     @bigbrother_group.command(name='unwatch', aliases=('uw',))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
-    async def unwatch_command(self, ctx: Context, user: Union[User, proxy_user], *, reason: str) -> None:
+    @with_role(*MODERATION_ROLES)
+    async def unwatch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """Stop relaying messages by the given `user`."""
         active_watches = await self.bot.api_client.get(
             self.api_endpoint,
diff --git a/bot/cogs/watchchannels/talentpool.py b/bot/cogs/watchchannels/talentpool.py
index 176c6f760..ad0c51fa6 100644
--- a/bot/cogs/watchchannels/talentpool.py
+++ b/bot/cogs/watchchannels/talentpool.py
@@ -1,20 +1,20 @@
 import logging
 import textwrap
 from collections import ChainMap
-from typing import Union
 
-from discord import Color, Embed, Member, User
-from discord.ext.commands import Bot, Cog, Context, group
+from discord import Color, Embed, Member
+from discord.ext.commands import Cog, Context, group
 
 from bot.api import ResponseCodeError
-from bot.constants import Channels, Guild, Roles, Webhooks
+from bot.bot import Bot
+from bot.constants import Channels, Guild, MODERATION_ROLES, STAFF_ROLES, Webhooks
+from bot.converters import FetchedMember
 from bot.decorators import with_role
 from bot.pagination import LinePaginator
 from bot.utils import time
-from .watchchannel import WatchChannel, proxy_user
+from .watchchannel import WatchChannel
 
 log = logging.getLogger(__name__)
-STAFF_ROLES = Roles.owner, Roles.admin, Roles.moderator, Roles.helpers    # <- In constants after the merge?
 
 
 class TalentPool(WatchChannel, Cog, name="Talentpool"):
@@ -31,13 +31,13 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         )
 
     @group(name='talentpool', aliases=('tp', 'talent', 'nomination', 'n'), invoke_without_command=True)
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
+    @with_role(*MODERATION_ROLES)
     async def nomination_group(self, ctx: Context) -> None:
         """Highlights the activity of helper nominees by relaying their messages to the talent pool channel."""
         await ctx.invoke(self.bot.get_command("help"), "talentpool")
 
     @nomination_group.command(name='watched', aliases=('all', 'list'))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
+    @with_role(*MODERATION_ROLES)
     async def watched_command(self, ctx: Context, update_cache: bool = True) -> None:
         """
         Shows the users that are currently being monitored in the talent pool.
@@ -48,8 +48,8 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         await self.list_watched_users(ctx, update_cache)
 
     @nomination_group.command(name='watch', aliases=('w', 'add', 'a'))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
-    async def watch_command(self, ctx: Context, user: Union[Member, User, proxy_user], *, reason: str) -> None:
+    @with_role(*STAFF_ROLES)
+    async def watch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """
         Relay messages sent by the given `user` to the `#talent-pool` channel.
 
@@ -69,7 +69,7 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
             return
 
         if user.id in self.watched_users:
-            await ctx.send(":x: The specified user is already being watched in the talent pool")
+            await ctx.send(f":x: {user} is already being watched in the talent pool")
             return
 
         # Manual request with `raise_for_status` as False because we want the actual response
@@ -113,8 +113,8 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         await ctx.send(msg)
 
     @nomination_group.command(name='history', aliases=('info', 'search'))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
-    async def history_command(self, ctx: Context, user: Union[User, proxy_user]) -> None:
+    @with_role(*MODERATION_ROLES)
+    async def history_command(self, ctx: Context, user: FetchedMember) -> None:
         """Shows the specified user's nomination history."""
         result = await self.bot.api_client.get(
             self.api_endpoint,
@@ -142,8 +142,8 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         )
 
     @nomination_group.command(name='unwatch', aliases=('end', ))
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
-    async def unwatch_command(self, ctx: Context, user: Union[User, proxy_user], *, reason: str) -> None:
+    @with_role(*MODERATION_ROLES)
+    async def unwatch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """
         Ends the active nomination of the specified user with the given reason.
 
@@ -170,13 +170,13 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         self._remove_user(user.id)
 
     @nomination_group.group(name='edit', aliases=('e',), invoke_without_command=True)
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
+    @with_role(*MODERATION_ROLES)
     async def nomination_edit_group(self, ctx: Context) -> None:
         """Commands to edit nominations."""
         await ctx.invoke(self.bot.get_command("help"), "talentpool", "edit")
 
     @nomination_edit_group.command(name='reason')
-    @with_role(Roles.owner, Roles.admin, Roles.moderator)
+    @with_role(*MODERATION_ROLES)
     async def edit_reason_command(self, ctx: Context, nomination_id: int, *, reason: str) -> None:
         """
         Edits the reason/unnominate reason for the nomination with the given `id` depending on the status.
diff --git a/bot/cogs/watchchannels/watchchannel.py b/bot/cogs/watchchannels/watchchannel.py
index 0bf75a924..eb787b083 100644
--- a/bot/cogs/watchchannels/watchchannel.py
+++ b/bot/cogs/watchchannels/watchchannel.py
@@ -9,10 +9,11 @@ from typing import Optional
 
 import dateutil.parser
 import discord
-from discord import Color, Embed, HTTPException, Message, Object, errors
-from discord.ext.commands import BadArgument, Bot, Cog, Context
+from discord import Color, Embed, HTTPException, Message, errors
+from discord.ext.commands import Cog, Context
 
 from bot.api import ResponseCodeError
+from bot.bot import Bot
 from bot.cogs.moderation import ModLog
 from bot.constants import BigBrother as BigBrotherConfig, Guild as GuildConfig, Icons
 from bot.pagination import LinePaginator
@@ -24,22 +25,6 @@ log = logging.getLogger(__name__)
 URL_RE = re.compile(r"(https?://[^\s]+)")
 
 
-def proxy_user(user_id: str) -> Object:
-    """A proxy user object that mocks a real User instance for when the later is not available."""
-    try:
-        user_id = int(user_id)
-    except ValueError:
-        raise BadArgument
-
-    user = Object(user_id)
-    user.mention = user.id
-    user.display_name = f"<@{user.id}>"
-    user.avatar_url_as = lambda static_format: None
-    user.bot = False
-
-    return user
-
-
 @dataclass
 class MessageHistory:
     """Represents a watch channel's message history."""
diff --git a/bot/cogs/wolfram.py b/bot/cogs/wolfram.py
index 3da349bd1..e6cae3bb8 100644
--- a/bot/cogs/wolfram.py
+++ b/bot/cogs/wolfram.py
@@ -7,8 +7,9 @@ import discord
 from dateutil.relativedelta import relativedelta
 from discord import Embed
 from discord.ext import commands
-from discord.ext.commands import Bot, BucketType, Cog, Context, check, group
+from discord.ext.commands import BucketType, Cog, Context, check, group
 
+from bot.bot import Bot
 from bot.constants import Colours, STAFF_ROLES, Wolfram
 from bot.pagination import ImagePaginator
 from bot.utils.time import humanize_delta
@@ -159,7 +160,7 @@ async def get_pod_pages(ctx: Context, bot: Bot, query: str) -> Optional[List[Tup
 class Wolfram(Cog):
     """Commands for interacting with the Wolfram|Alpha API."""
 
-    def __init__(self, bot: commands.Bot):
+    def __init__(self, bot: Bot):
         self.bot = bot
 
     @group(name="wolfram", aliases=("wolf", "wa"), invoke_without_command=True)
@@ -274,7 +275,6 @@ class Wolfram(Cog):
             await send_embed(ctx, message, color)
 
 
-def setup(bot: commands.Bot) -> None:
-    """Wolfram cog load."""
+def setup(bot: Bot) -> None:
+    """Load the Wolfram cog."""
     bot.add_cog(Wolfram(bot))
-    log.info("Cog loaded: Wolfram")
diff --git a/bot/constants.py b/bot/constants.py
index 1deeaa3b8..fe8e57322 100644
--- a/bot/constants.py
+++ b/bot/constants.py
@@ -236,6 +236,13 @@ class Colours(metaclass=YAMLGetter):
     soft_orange: int
 
 
+class DuckPond(metaclass=YAMLGetter):
+    section = "duck_pond"
+
+    threshold: int
+    custom_emojis: List[int]
+
+
 class Emojis(metaclass=YAMLGetter):
     section = "style"
     subsection = "emojis"
@@ -244,21 +251,37 @@ class Emojis(metaclass=YAMLGetter):
     defcon_enabled: str  # noqa: E704
     defcon_updated: str  # noqa: E704
 
-    green_chevron: str
-    red_chevron: str
-    white_chevron: str
-    bb_message: str
-
     status_online: str
     status_offline: str
     status_idle: str
     status_dnd: str
 
+    failmail: str
+    trashcan: str
+
     bullet: str
     new: str
     pencil: str
     cross_mark: str
 
+    ducky_yellow: int
+    ducky_blurple: int
+    ducky_regal: int
+    ducky_camo: int
+    ducky_ninja: int
+    ducky_devil: int
+    ducky_tube: int
+    ducky_hunt: int
+    ducky_wizard: int
+    ducky_party: int
+    ducky_angel: int
+    ducky_maul: int
+    ducky_santa: int
+
+    upvotes: str
+    comments: str
+    user: str
+
 
 class Icons(metaclass=YAMLGetter):
     section = "style"
@@ -308,6 +331,13 @@ class Icons(metaclass=YAMLGetter):
 
     questionmark: str
 
+    superstarify: str
+    unsuperstarify: str
+
+    voice_state_blue: str
+    voice_state_green: str
+    voice_state_red: str
+
 
 class CleanMessages(metaclass=YAMLGetter):
     section = "bot"
@@ -328,13 +358,16 @@ class Channels(metaclass=YAMLGetter):
     subsection = "channels"
 
     admins: int
+    admin_spam: int
     announcements: int
+    attachment_log: int
     big_brother_logs: int
     bot: int
     checkpoint_test: int
     defcon: int
     devlog: int
     devtest: int
+    esoteric: int
     help_0: int
     help_1: int
     help_2: int
@@ -345,17 +378,22 @@ class Channels(metaclass=YAMLGetter):
     help_7: int
     helpers: int
     message_log: int
+    meta: int
+    mod_spam: int
+    mods: int
     mod_alerts: int
     modlog: int
     off_topic_0: int
     off_topic_1: int
     off_topic_2: int
+    organisation: int
     python: int
     reddit: int
     talent_pool: int
     userlog: int
     user_event_a: int
     verification: int
+    voice_log: int
 
 
 class Webhooks(metaclass=YAMLGetter):
@@ -364,6 +402,8 @@ class Webhooks(metaclass=YAMLGetter):
 
     talent_pool: int
     big_brother: int
+    reddit: int
+    duck_pond: int
 
 
 class Roles(metaclass=YAMLGetter):
@@ -391,6 +431,7 @@ class Guild(metaclass=YAMLGetter):
 
     id: int
     ignored: List[int]
+    staff_channels: List[int]
 
 
 class Keys(metaclass=YAMLGetter):
@@ -438,8 +479,9 @@ class URLs(metaclass=YAMLGetter):
 class Reddit(metaclass=YAMLGetter):
     section = "reddit"
 
-    request_delay: int
     subreddits: list
+    client_id: str
+    secret: str
 
 
 class Wolfram(metaclass=YAMLGetter):
@@ -460,6 +502,12 @@ class AntiSpam(metaclass=YAMLGetter):
     rules: Dict[str, Dict[str, int]]
 
 
+class AntiMalware(metaclass=YAMLGetter):
+    section = "anti_malware"
+
+    whitelist: list
+
+
 class BigBrother(metaclass=YAMLGetter):
     section = 'big_brother'
 
@@ -475,6 +523,13 @@ class Free(metaclass=YAMLGetter):
     cooldown_per: float
 
 
+class Mention(metaclass=YAMLGetter):
+    section = 'mention'
+
+    message_timeout: int
+    reset_delay: int
+
+
 class RedirectOutput(metaclass=YAMLGetter):
     section = 'redirect_output'
 
@@ -482,6 +537,32 @@ class RedirectOutput(metaclass=YAMLGetter):
     delete_delay: int
 
 
+class Event(Enum):
+    """
+    Event names. This does not include every event (for example, raw
+    events aren't here), but only events used in ModLog for now.
+    """
+
+    guild_channel_create = "guild_channel_create"
+    guild_channel_delete = "guild_channel_delete"
+    guild_channel_update = "guild_channel_update"
+    guild_role_create = "guild_role_create"
+    guild_role_delete = "guild_role_delete"
+    guild_role_update = "guild_role_update"
+    guild_update = "guild_update"
+
+    member_join = "member_join"
+    member_remove = "member_remove"
+    member_ban = "member_ban"
+    member_unban = "member_unban"
+    member_update = "member_update"
+
+    message_delete = "message_delete"
+    message_edit = "message_edit"
+
+    voice_state_update = "voice_state_update"
+
+
 # Debug mode
 DEBUG_MODE = True if 'local' in os.environ.get("SITE_URL", "local") else False
 
@@ -493,6 +574,12 @@ PROJECT_ROOT = os.path.abspath(os.path.join(BOT_DIR, os.pardir))
 MODERATION_ROLES = Roles.moderator, Roles.admin, Roles.owner
 STAFF_ROLES = Roles.helpers, Roles.moderator, Roles.admin, Roles.owner
 
+# Roles combinations
+STAFF_CHANNELS = Guild.staff_channels
+
+# Default Channel combinations
+MODERATION_CHANNELS = Channels.admins, Channels.admin_spam, Channels.mod_alerts, Channels.mods, Channels.mod_spam
+
 
 # Bot replies
 NEGATIVE_REPLIES = [
@@ -547,27 +634,3 @@ ERROR_REPLIES = [
     "Noooooo!!",
     "I can't believe you've done this",
 ]
-
-
-class Event(Enum):
-    """
-    Event names. This does not include every event (for example, raw
-    events aren't here), but only events used in ModLog for now.
-    """
-
-    guild_channel_create = "guild_channel_create"
-    guild_channel_delete = "guild_channel_delete"
-    guild_channel_update = "guild_channel_update"
-    guild_role_create = "guild_role_create"
-    guild_role_delete = "guild_role_delete"
-    guild_role_update = "guild_role_update"
-    guild_update = "guild_update"
-
-    member_join = "member_join"
-    member_remove = "member_remove"
-    member_ban = "member_ban"
-    member_unban = "member_unban"
-    member_update = "member_update"
-
-    message_delete = "message_delete"
-    message_edit = "message_edit"
diff --git a/bot/converters.py b/bot/converters.py
index cf0496541..cca57a02d 100644
--- a/bot/converters.py
+++ b/bot/converters.py
@@ -1,20 +1,39 @@
 import logging
 import re
+import typing as t
 from datetime import datetime
 from ssl import CertificateError
-from typing import Union
 
 import dateutil.parser
 import dateutil.tz
 import discord
 from aiohttp import ClientConnectorError
 from dateutil.relativedelta import relativedelta
-from discord.ext.commands import BadArgument, Context, Converter
+from discord.ext.commands import BadArgument, Context, Converter, UserConverter
 
 
 log = logging.getLogger(__name__)
 
 
+def allowed_strings(*values, preserve_case: bool = False) -> t.Callable[[str], str]:
+    """
+    Return a converter which only allows arguments equal to one of the given values.
+
+    Unless preserve_case is True, the argument is converted to lowercase. All values are then
+    expected to have already been given in lowercase too.
+    """
+    def converter(arg: str) -> str:
+        if not preserve_case:
+            arg = arg.lower()
+
+        if arg not in values:
+            raise BadArgument(f"Only the following values are allowed:\n```{', '.join(values)}```")
+        else:
+            return arg
+
+    return converter
+
+
 class ValidPythonIdentifier(Converter):
     """
     A converter that checks whether the given string is a valid Python identifier.
@@ -70,7 +89,7 @@ class InfractionSearchQuery(Converter):
     """A converter that checks if the argument is a Discord user, and if not, falls back to a string."""
 
     @staticmethod
-    async def convert(ctx: Context, arg: str) -> Union[discord.Member, str]:
+    async def convert(ctx: Context, arg: str) -> t.Union[discord.Member, str]:
         """Check if the argument is a Discord user, and if not, falls back to a string."""
         try:
             maybe_snowflake = arg.strip("<@!>")
@@ -259,3 +278,75 @@ class ISODateTime(Converter):
             dt = dt.replace(tzinfo=None)
 
         return dt
+
+
+def proxy_user(user_id: str) -> discord.Object:
+    """
+    Create a proxy user object from the given id.
+
+    Used when a Member or User object cannot be resolved.
+    """
+    log.trace(f"Attempting to create a proxy user for the user id {user_id}.")
+
+    try:
+        user_id = int(user_id)
+    except ValueError:
+        log.debug(f"Failed to create proxy user {user_id}: could not convert to int.")
+        raise BadArgument(f"User ID `{user_id}` is invalid - could not convert to an integer.")
+
+    user = discord.Object(user_id)
+    user.mention = user.id
+    user.display_name = f"<@{user.id}>"
+    user.avatar_url_as = lambda static_format: None
+    user.bot = False
+
+    return user
+
+
+class FetchedUser(UserConverter):
+    """
+    Converts to a `discord.User` or, if it fails, a `discord.Object`.
+
+    Unlike the default `UserConverter`, which only does lookups via the global user cache, this
+    converter attempts to fetch the user via an API call to Discord when the using the cache is
+    unsuccessful.
+
+    If the fetch also fails and the error doesn't imply the user doesn't exist, then a
+    `discord.Object` is returned via the `user_proxy` converter.
+
+    The lookup strategy is as follows (in order):
+
+    1. Lookup by ID.
+    2. Lookup by mention.
+    3. Lookup by name#discrim
+    4. Lookup by name
+    5. Lookup via API
+    6. Create a proxy user with discord.Object
+    """
+
+    async def convert(self, ctx: Context, arg: str) -> t.Union[discord.User, discord.Object]:
+        """Convert the `arg` to a `discord.User` or `discord.Object`."""
+        try:
+            return await super().convert(ctx, arg)
+        except BadArgument:
+            pass
+
+        try:
+            user_id = int(arg)
+            log.trace(f"Fetching user {user_id}...")
+            return await ctx.bot.fetch_user(user_id)
+        except ValueError:
+            log.debug(f"Failed to fetch user {arg}: could not convert to int.")
+            raise BadArgument(f"The provided argument can't be turned into integer: `{arg}`")
+        except discord.HTTPException as e:
+            # If the Discord error isn't `Unknown user`, return a proxy instead
+            if e.code != 10013:
+                log.warning(f"Failed to fetch user, returning a proxy instead: status {e.status}")
+                return proxy_user(arg)
+
+            log.debug(f"Failed to fetch user {arg}: user does not exist.")
+            raise BadArgument(f"User `{arg}` does not exist")
+
+
+Expiry = t.Union[Duration, ISODateTime]
+FetchedMember = t.Union[discord.Member, FetchedUser]
diff --git a/bot/decorators.py b/bot/decorators.py
index b31324f36..185521552 100644
--- a/bot/decorators.py
+++ b/bot/decorators.py
@@ -27,11 +27,23 @@ class InChannelCheckFailure(CheckFailure):
         super().__init__(f"Sorry, but you may only use this command within {channels_str}.")
 
 
-def in_channel(*channels: int, bypass_roles: Container[int] = None) -> Callable:
-    """Checks that the message is in a whitelisted channel or optionally has a bypass role."""
+def in_channel(
+    *channels: int,
+    hidden_channels: Container[int] = None,
+    bypass_roles: Container[int] = None
+) -> Callable:
+    """
+    Checks that the message is in a whitelisted channel or optionally has a bypass role.
+
+    Hidden channels are channels which will not be displayed in the InChannelCheckFailure error
+    message.
+    """
+    hidden_channels = hidden_channels or []
+    bypass_roles = bypass_roles or []
+
     def predicate(ctx: Context) -> bool:
         """In-channel checker predicate."""
-        if ctx.channel.id in channels:
+        if ctx.channel.id in channels or ctx.channel.id in hidden_channels:
             log.debug(f"{ctx.author} tried to call the '{ctx.command.name}' command. "
                       f"The command was used in a whitelisted channel.")
             return True
diff --git a/bot/interpreter.py b/bot/interpreter.py
index a42b45a2d..8b7268746 100644
--- a/bot/interpreter.py
+++ b/bot/interpreter.py
@@ -2,7 +2,9 @@ from code import InteractiveInterpreter
 from io import StringIO
 from typing import Any
 
-from discord.ext.commands import Bot, Context
+from discord.ext.commands import Context
+
+from bot.bot import Bot
 
 CODE_TEMPLATE = """
 async def _func():
@@ -20,8 +22,8 @@ class Interpreter(InteractiveInterpreter):
     write_callable = None
 
     def __init__(self, bot: Bot):
-        _locals = {"bot": bot}
-        super().__init__(_locals)
+        locals_ = {"bot": bot}
+        super().__init__(locals_)
 
     async def run(self, code: str, ctx: Context, io: StringIO, *args, **kwargs) -> Any:
         """Execute the provided source code as the bot & return the output."""
diff --git a/bot/pagination.py b/bot/pagination.py
index 76082f459..35870c040 100644
--- a/bot/pagination.py
+++ b/bot/pagination.py
@@ -6,11 +6,13 @@ from discord import Embed, Member, Message, Reaction
 from discord.abc import User
 from discord.ext.commands import Context, Paginator
 
+from bot import constants
+
 FIRST_EMOJI = "\u23EE"   # [:track_previous:]
 LEFT_EMOJI = "\u2B05"    # [:arrow_left:]
 RIGHT_EMOJI = "\u27A1"   # [:arrow_right:]
 LAST_EMOJI = "\u23ED"    # [:track_next:]
-DELETE_EMOJI = "\u274c"  # [:x:]
+DELETE_EMOJI = constants.Emojis.trashcan  # [:trashcan:]
 
 PAGINATION_EMOJI = [FIRST_EMOJI, LEFT_EMOJI, RIGHT_EMOJI, LAST_EMOJI, DELETE_EMOJI]
 
@@ -131,7 +133,7 @@ class LinePaginator(Paginator):
                     # Reaction is on this message
                     reaction_.message.id == message.id,
                     # Reaction is one of the pagination emotes
-                    reaction_.emoji in PAGINATION_EMOJI,
+                    str(reaction_.emoji) in PAGINATION_EMOJI,
                     # Reaction was not made by the Bot
                     user_.id != ctx.bot.user.id,
                     # There were no restrictions
@@ -203,9 +205,9 @@ class LinePaginator(Paginator):
                 log.debug("Timed out waiting for a reaction")
                 break  # We're done, no reactions for the last 5 minutes
 
-            if reaction.emoji == DELETE_EMOJI:
+            if str(reaction.emoji) == DELETE_EMOJI:
                 log.debug("Got delete reaction")
-                break
+                return await message.delete()
 
             if reaction.emoji == FIRST_EMOJI:
                 await message.remove_reaction(reaction.emoji, user)
@@ -342,7 +344,7 @@ class ImagePaginator(Paginator):
                 # Reaction is on the same message sent
                 reaction_.message.id == message.id,
                 # The reaction is part of the navigation menu
-                reaction_.emoji in PAGINATION_EMOJI,
+                str(reaction_.emoji) in PAGINATION_EMOJI,
                 # The reactor is not a bot
                 not member.bot
             ))
@@ -388,10 +390,10 @@ class ImagePaginator(Paginator):
             # Deletes the users reaction
             await message.remove_reaction(reaction.emoji, user)
 
-            # Delete reaction press - [:x:]
-            if reaction.emoji == DELETE_EMOJI:
+            # Delete reaction press - [:trashcan:]
+            if str(reaction.emoji) == DELETE_EMOJI:
                 log.debug("Got delete reaction")
-                break
+                return await message.delete()
 
             # First reaction press - [:track_previous:]
             if reaction.emoji == FIRST_EMOJI:
diff --git a/bot/rules/attachments.py b/bot/rules/attachments.py
index c550aed76..00bb2a949 100644
--- a/bot/rules/attachments.py
+++ b/bot/rules/attachments.py
@@ -7,14 +7,14 @@ async def apply(
     last_message: Message, recent_messages: List[Message], config: Dict[str, int]
 ) -> Optional[Tuple[str, Iterable[Member], Iterable[Message]]]:
     """Detects total attachments exceeding the limit sent by a single user."""
-    relevant_messages = [last_message] + [
+    relevant_messages = tuple(
         msg
         for msg in recent_messages
         if (
             msg.author == last_message.author
             and len(msg.attachments) > 0
         )
-    ]
+    )
     total_recent_attachments = sum(len(msg.attachments) for msg in relevant_messages)
 
     if total_recent_attachments > config['max']:
diff --git a/bot/utils/checks.py b/bot/utils/checks.py
index 19f64ff9f..db56c347c 100644
--- a/bot/utils/checks.py
+++ b/bot/utils/checks.py
@@ -1,6 +1,8 @@
+import datetime
 import logging
+from typing import Callable, Iterable
 
-from discord.ext.commands import Context
+from discord.ext.commands import BucketType, Cog, Command, CommandOnCooldown, Context, Cooldown, CooldownMapping
 
 log = logging.getLogger(__name__)
 
@@ -36,9 +38,53 @@ def without_role_check(ctx: Context, *role_ids: int) -> bool:
     return check
 
 
-def in_channel_check(ctx: Context, channel_id: int) -> bool:
-    """Checks if the command was executed inside of the specified channel."""
-    check = ctx.channel.id == channel_id
+def in_channel_check(ctx: Context, *channel_ids: int) -> bool:
+    """Checks if the command was executed inside the list of specified channels."""
+    check = ctx.channel.id in channel_ids
     log.trace(f"{ctx.author} tried to call the '{ctx.command.name}' command. "
               f"The result of the in_channel check was {check}.")
     return check
+
+
+def cooldown_with_role_bypass(rate: int, per: float, type: BucketType = BucketType.default, *,
+                              bypass_roles: Iterable[int]) -> Callable:
+    """
+    Applies a cooldown to a command, but allows members with certain roles to be ignored.
+
+    NOTE: this replaces the `Command.before_invoke` callback, which *might* introduce problems in the future.
+    """
+    # make it a set so lookup is hash based
+    bypass = set(bypass_roles)
+
+    # this handles the actual cooldown logic
+    buckets = CooldownMapping(Cooldown(rate, per, type))
+
+    # will be called after the command has been parse but before it has been invoked, ensures that
+    # the cooldown won't be updated if the user screws up their input to the command
+    async def predicate(cog: Cog, ctx: Context) -> None:
+        nonlocal bypass, buckets
+
+        if any(role.id in bypass for role in ctx.author.roles):
+            return
+
+        # cooldown logic, taken from discord.py internals
+        current = ctx.message.created_at.replace(tzinfo=datetime.timezone.utc).timestamp()
+        bucket = buckets.get_bucket(ctx.message)
+        retry_after = bucket.update_rate_limit(current)
+        if retry_after:
+            raise CommandOnCooldown(bucket, retry_after)
+
+    def wrapper(command: Command) -> Command:
+        # NOTE: this could be changed if a subclass of Command were to be used. I didn't see the need for it
+        # so I just made it raise an error when the decorator is applied before the actual command object exists.
+        #
+        # if the `before_invoke` detail is ever a problem then I can quickly just swap over.
+        if not isinstance(command, Command):
+            raise TypeError('Decorator `cooldown_with_role_bypass` must be applied after the command decorator. '
+                            'This means it has to be above the command decorator in the code.')
+
+        command._before_invoke = predicate
+
+        return command
+
+    return wrapper
diff --git a/bot/utils/messages.py b/bot/utils/messages.py
index 549b33ca6..a36edc774 100644
--- a/bot/utils/messages.py
+++ b/bot/utils/messages.py
@@ -1,7 +1,8 @@
 import asyncio
 import contextlib
+import logging
 from io import BytesIO
-from typing import Optional, Sequence, Union
+from typing import List, Optional, Sequence, Union
 
 from discord import Client, Embed, File, Member, Message, Reaction, TextChannel, Webhook
 from discord.abc import Snowflake
@@ -9,13 +10,13 @@ from discord.errors import HTTPException
 
 from bot.constants import Emojis
 
-MAX_SIZE = 1024 * 1024 * 8  # 8 Mebibytes
+log = logging.getLogger(__name__)
 
 
 async def wait_for_deletion(
     message: Message,
     user_ids: Sequence[Snowflake],
-    deletion_emojis: Sequence[str] = (Emojis.cross_mark,),
+    deletion_emojis: Sequence[str] = (Emojis.trashcan,),
     timeout: float = 60 * 5,
     attach_emojis: bool = True,
     client: Optional[Client] = None
@@ -39,10 +40,10 @@ async def wait_for_deletion(
             await message.add_reaction(emoji)
 
     def check(reaction: Reaction, user: Member) -> bool:
-        """Check that the deletion emoji is reacted by the approprite user."""
+        """Check that the deletion emoji is reacted by the appropriate user."""
         return (
             reaction.message.id == message.id
-            and reaction.emoji in deletion_emojis
+            and str(reaction.emoji) in deletion_emojis
             and user.id in user_ids
         )
 
@@ -51,42 +52,58 @@ async def wait_for_deletion(
         await message.delete()
 
 
-async def send_attachments(message: Message, destination: Union[TextChannel, Webhook]) -> None:
+async def send_attachments(
+    message: Message,
+    destination: Union[TextChannel, Webhook],
+    link_large: bool = True
+) -> List[str]:
     """
-    Re-uploads each attachment in a message to the given channel or webhook.
+    Re-upload the message's attachments to the destination and return a list of their new URLs.
 
-    Each attachment is sent as a separate message to more easily comply with the 8 MiB request size limit.
-    If attachments are too large, they are instead grouped into a single embed which links to them.
+    Each attachment is sent as a separate message to more easily comply with the request/file size
+    limit. If link_large is True, attachments which are too large are instead grouped into a single
+    embed which links to them.
     """
     large = []
+    urls = []
     for attachment in message.attachments:
+        failure_msg = (
+            f"Failed to re-upload attachment {attachment.filename} from message {message.id}"
+        )
+
         try:
-            # This should avoid most files that are too large, but some may get through hence the try-catch.
             # Allow 512 bytes of leeway for the rest of the request.
-            if attachment.size <= MAX_SIZE - 512:
+            # This should avoid most files that are too large,
+            # but some may get through hence the try-catch.
+            if attachment.size <= destination.guild.filesize_limit - 512:
                 with BytesIO() as file:
-                    await attachment.save(file)
+                    await attachment.save(file, use_cached=True)
                     attachment_file = File(file, filename=attachment.filename)
 
                     if isinstance(destination, TextChannel):
-                        await destination.send(file=attachment_file)
+                        msg = await destination.send(file=attachment_file)
+                        urls.append(msg.attachments[0].url)
                     else:
                         await destination.send(
                             file=attachment_file,
                             username=message.author.display_name,
                             avatar_url=message.author.avatar_url
                         )
-            else:
+            elif link_large:
                 large.append(attachment)
+            else:
+                log.warning(f"{failure_msg} because it's too large.")
         except HTTPException as e:
-            if e.status == 413:
+            if link_large and e.status == 413:
                 large.append(attachment)
             else:
-                raise
+                log.warning(f"{failure_msg} with status {e.status}.")
 
-    if large:
-        embed = Embed(description=f"\n".join(f"[{attachment.filename}]({attachment.url})" for attachment in large))
+    if link_large and large:
+        desc = f"\n".join(f"[{attachment.filename}]({attachment.url})" for attachment in large)
+        embed = Embed(description=desc)
         embed.set_footer(text="Attachments exceed upload size limit.")
+
         if isinstance(destination, TextChannel):
             await destination.send(embed=embed)
         else:
@@ -95,3 +112,5 @@ async def send_attachments(message: Message, destination: Union[TextChannel, Web
                 username=message.author.display_name,
                 avatar_url=message.author.avatar_url
             )
+
+    return urls
diff --git a/bot/utils/scheduling.py b/bot/utils/scheduling.py
index 08abd91d7..ee6c0a8e6 100644
--- a/bot/utils/scheduling.py
+++ b/bot/utils/scheduling.py
@@ -36,11 +36,15 @@ class Scheduler(metaclass=CogABCMeta):
         `task_data` is passed to `Scheduler._scheduled_expiration`
         """
         if task_id in self.scheduled_tasks:
+            log.debug(
+                f"{self.cog_name}: did not schedule task #{task_id}; task was already scheduled."
+            )
             return
 
         task: asyncio.Task = create_task(loop, self._scheduled_task(task_data))
 
         self.scheduled_tasks[task_id] = task
+        log.debug(f"{self.cog_name}: scheduled task #{task_id}.")
 
     def cancel_task(self, task_id: str) -> None:
         """Un-schedules a task."""
@@ -51,7 +55,7 @@ class Scheduler(metaclass=CogABCMeta):
             return
 
         task.cancel()
-        log.debug(f"{self.cog_name}: Unscheduled {task_id}.")
+        log.debug(f"{self.cog_name}: unscheduled task #{task_id}.")
         del self.scheduled_tasks[task_id]
 
 
diff --git a/bot/utils/time.py b/bot/utils/time.py
index 2aea2c099..7416f36e0 100644
--- a/bot/utils/time.py
+++ b/bot/utils/time.py
@@ -111,3 +111,55 @@ async def wait_until(time: datetime.datetime, start: Optional[datetime.datetime]
 def format_infraction(timestamp: str) -> str:
     """Format an infraction timestamp to a more readable ISO 8601 format."""
     return dateutil.parser.isoparse(timestamp).strftime(INFRACTION_FORMAT)
+
+
+def format_infraction_with_duration(
+    expiry: Optional[str],
+    date_from: Optional[datetime.datetime] = None,
+    max_units: int = 2
+) -> Optional[str]:
+    """
+    Format an infraction timestamp to a more readable ISO 8601 format WITH the duration.
+
+    Returns a human-readable version of the duration between datetime.utcnow() and an expiry.
+    Unlike `humanize_delta`, this function will force the `precision` to be `seconds` by not passing it.
+    `max_units` specifies the maximum number of units of time to include (e.g. 1 may include days but not hours).
+    By default, max_units is 2.
+    """
+    if not expiry:
+        return None
+
+    date_from = date_from or datetime.datetime.utcnow()
+    date_to = dateutil.parser.isoparse(expiry).replace(tzinfo=None, microsecond=0)
+
+    expiry_formatted = format_infraction(expiry)
+
+    duration = humanize_delta(relativedelta(date_to, date_from), max_units=max_units)
+    duration_formatted = f" ({duration})" if duration else ''
+
+    return f"{expiry_formatted}{duration_formatted}"
+
+
+def until_expiration(
+    expiry: Optional[str],
+    now: Optional[datetime.datetime] = None,
+    max_units: int = 2
+) -> Optional[str]:
+    """
+    Get the remaining time until infraction's expiration, in a human-readable version of the relativedelta.
+
+    Returns a human-readable version of the remaining duration between datetime.utcnow() and an expiry.
+    Unlike `humanize_delta`, this function will force the `precision` to be `seconds` by not passing it.
+    `max_units` specifies the maximum number of units of time to include (e.g. 1 may include days but not hours).
+    By default, max_units is 2.
+    """
+    if not expiry:
+        return None
+
+    now = now or datetime.datetime.utcnow()
+    since = dateutil.parser.isoparse(expiry).replace(tzinfo=None, microsecond=0)
+
+    if since < now:
+        return None
+
+    return humanize_delta(relativedelta(since, now), max_units=max_units)
diff --git a/config-default.yml b/config-default.yml
index 0dac9bf9f..fda14b511 100644
--- a/config-default.yml
+++ b/config-default.yml
@@ -22,21 +22,37 @@ style:
         defcon_enabled:  "<:defconenabled:470326274213150730>"
         defcon_updated:  "<:defconsettingsupdated:470326274082996224>"
 
-        green_chevron: "<:greenchevron:418104310329769993>"
-        red_chevron:   "<:redchevron:418112778184818698>"
-        white_chevron: "<:whitechevron:418110396973711363>"
-        bb_message:    "<:bbmessage:476273120999636992>"
-
         status_online:  "<:status_online:470326272351010816>"
         status_idle:    "<:status_idle:470326266625785866>"
         status_dnd:     "<:status_dnd:470326272082313216>"
         status_offline: "<:status_offline:470326266537705472>"
 
+        failmail: "<:failmail:633660039931887616>"
+        trashcan: "<:trashcan:637136429717389331>"
+
         bullet:     "\u2022"
         pencil:     "\u270F"
         new:        "\U0001F195"
         cross_mark: "\u274C"
 
+        ducky_yellow:   &DUCKY_YELLOW   574951975574175744
+        ducky_blurple:  &DUCKY_BLURPLE  574951975310065675
+        ducky_regal:    &DUCKY_REGAL    637883439185395712
+        ducky_camo:     &DUCKY_CAMO     637914731566596096
+        ducky_ninja:    &DUCKY_NINJA    637923502535606293
+        ducky_devil:    &DUCKY_DEVIL    637925314982576139
+        ducky_tube:     &DUCKY_TUBE     637881368008851456
+        ducky_hunt:     &DUCKY_HUNT     639355090909528084
+        ducky_wizard:   &DUCKY_WIZARD   639355996954689536
+        ducky_party:    &DUCKY_PARTY    639468753440210977
+        ducky_angel:    &DUCKY_ANGEL    640121935610511361
+        ducky_maul:     &DUCKY_MAUL     640137724958867467
+        ducky_santa:    &DUCKY_SANTA    655360331002019870
+
+        upvotes:        "<:upvotes:638729835245731840>"
+        comments:       "<:comments:638729835073765387>"
+        user:           "<:user:638729835442602003>"
+
     icons:
         crown_blurple: "https://cdn.discordapp.com/emojis/469964153289965568.png"
         crown_green:   "https://cdn.discordapp.com/emojis/469964154719961088.png"
@@ -82,6 +98,13 @@ style:
 
         questionmark: "https://cdn.discordapp.com/emojis/512367613339369475.png"
 
+        superstarify: "https://cdn.discordapp.com/emojis/636288153044516874.png"
+        unsuperstarify: "https://cdn.discordapp.com/emojis/636288201258172446.png"
+
+        voice_state_blue: "https://cdn.discordapp.com/emojis/656899769662439456.png"
+        voice_state_green: "https://cdn.discordapp.com/emojis/656899770094452754.png"
+        voice_state_red: "https://cdn.discordapp.com/emojis/656899769905709076.png"
+
 guild:
     id: 267624335836053506
 
@@ -90,13 +113,17 @@ guild:
 
     channels:
         admins:            &ADMINS        365960823622991872
+        admin_spam:        &ADMIN_SPAM    563594791770914816
+        admins_voice:      &ADMINS_VOICE  500734494840717332
         announcements:                    354619224620138496
+        attachment_log:    &ATTCH_LOG     649243850006855680
         big_brother_logs:  &BBLOGS        468507907357409333
         bot:                              267659945086812160
         checkpoint_test:                  422077681434099723
-        defcon:                           464469101889454091
+        defcon:            &DEFCON        464469101889454091
         devlog:            &DEVLOG        622895325144940554
         devtest:           &DEVTEST       414574275865870337
+        esoteric:                         470884583684964352
         help_0:                           303906576991780866
         help_1:                           303906556754395136
         help_2:                           303906514266226689
@@ -105,22 +132,29 @@ guild:
         help_5:                           454941769734422538
         help_6:                           587375753306570782
         help_7:                           587375768556797982
-        helpers:                          385474242440986624
+        helpers:           &HELPERS       385474242440986624
         message_log:       &MESSAGE_LOG   467752170159079424
+        meta:                             429409067623251969
+        mod_spam:          &MOD_SPAM      620607373828030464
+        mods:              &MODS          305126844661760000
         mod_alerts:                       473092532147060736
         modlog:            &MODLOG        282638479504965634
         off_topic_0:                      291284109232308226
         off_topic_1:                      463035241142026251
         off_topic_2:                      463035268514185226
+        organisation:      &ORGANISATION  551789653284356126
         python:                           267624335836053506
         reddit:                           458224812528238616
         staff_lounge:      &STAFF_LOUNGE  464905259261755392
+        staff_voice:       &STAFF_VOICE   412375055910043655
         talent_pool:       &TALENT_POOL   534321732593647616
         userlog:                          528976905546760203
         user_event_a:      &USER_EVENT_A  592000283102674944
         verification:                     352442727016693763
+        voice_log:                        640292421988646961
 
-    ignored: [*ADMINS, *MESSAGE_LOG, *MODLOG]
+    staff_channels: [*ADMINS, *ADMIN_SPAM, *MOD_SPAM, *MODS, *HELPERS, *ORGANISATION, *DEFCON]
+    ignored: [*ADMINS, *MESSAGE_LOG, *MODLOG, *ADMINS_VOICE, *STAFF_VOICE, *ATTCH_LOG]
 
     roles:
         admin:             &ADMIN_ROLE      267628507062992896
@@ -129,7 +163,7 @@ guild:
         contributor:                        295488872404484098
         core_developer:                     587606783669829632
         helpers:                            267630620367257601
-        jammer:                             423054537079783434
+        jammer:                             591786436651646989
         moderator:         &MOD_ROLE        267629731250176001
         muted:             &MUTED_ROLE      277914926603829249
         owner:             &OWNER_ROLE      267627879762755584
@@ -141,6 +175,8 @@ guild:
     webhooks:
         talent_pool:                        569145364800602132
         big_brother:                        569133704568373283
+        reddit:                             635408384794951680
+        duck_pond:                          637821475327311927
 
 
 filter:
@@ -174,6 +210,12 @@ filter:
         - 544525886180032552  # kennethreitz.org
         - 590806733924859943  # Discord Hack Week
         - 423249981340778496  # Kivy
+        - 197038439483310086  # Discord Testers
+        - 286633898581164032  # Ren'Py
+        - 349505959032389632  # PyGame
+        - 438622377094414346  # Pyglet
+        - 524691714909274162  # Panda3D
+        - 336642139381301249  # discord.py
 
     domain_blacklist:
         - pornhub.com
@@ -322,10 +364,41 @@ anti_spam:
             max: 3
 
 
+anti_malware:
+    whitelist:
+        - '.3gp'
+        - '.3g2'
+        - '.avi'
+        - '.bmp'
+        - '.gif'
+        - '.h264'
+        - '.jpg'
+        - '.jpeg'
+        - '.m4v'
+        - '.mkv'
+        - '.mov'
+        - '.mp4'
+        - '.mpeg'
+        - '.mpg'
+        - '.png'
+        - '.tiff'
+        - '.wmv'
+        - '.svg'
+        - '.psd'  # Photoshop
+        - '.ai'   # Illustrator
+        - '.aep'  # After Effects
+        - '.xcf'  # GIMP
+        - '.mp3'
+        - '.wav'
+        - '.ogg'
+        - '.md'
+
+
 reddit:
-    request_delay: 60
     subreddits:
         - 'r/Python'
+    client_id: !ENV "REDDIT_CLIENT_ID"
+    secret:    !ENV "REDDIT_SECRET"
 
 
 wolfram:
@@ -347,9 +420,17 @@ free:
     cooldown_rate: 1
     cooldown_per: 60.0
 
+mention:
+    message_timeout: 300
+    reset_delay: 5
+
 redirect_output:
     delete_invocation: true
     delete_delay: 15
 
+duck_pond:
+    threshold: 5
+    custom_emojis: [*DUCKY_YELLOW, *DUCKY_BLURPLE, *DUCKY_CAMO, *DUCKY_DEVIL, *DUCKY_NINJA, *DUCKY_REGAL, *DUCKY_TUBE, *DUCKY_HUNT, *DUCKY_WIZARD, *DUCKY_PARTY, *DUCKY_ANGEL, *DUCKY_MAUL, *DUCKY_SANTA]
+
 config:
     required_keys: ['bot.token']
diff --git a/docker-compose.yml b/docker-compose.yml
index f79fdba58..7281c7953 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -42,3 +42,5 @@ services:
     environment:
       BOT_TOKEN: ${BOT_TOKEN}
       BOT_API_KEY: badbot13m0n8f570f942013fc818f234916ca531
+      REDDIT_CLIENT_ID: ${REDDIT_CLIENT_ID}
+      REDDIT_SECRET: ${REDDIT_SECRET}
diff --git a/tests/README.md b/tests/README.md
new file mode 100644
index 000000000..be78821bf
--- /dev/null
+++ b/tests/README.md
@@ -0,0 +1,221 @@
+# Testing our Bot
+
+Our bot is one of the most important tools we have for running our community. As we don't want that tool break, we decided that we wanted to write unit tests for it. We hope that in the future, we'll have a 100% test coverage for the bot. This guide will help you get started with writing the tests needed to achieve that.
+
+_**Note:** This is a practical guide to getting started with writing tests for our bot, not a general introduction to writing unit tests in Python. If you're looking for a more general introduction, you can take a look at the [Additional resources](#additional-resources) section at the bottom of this page._
+
+## Tools
+
+We are using the following modules and packages for our unit tests:
+
+- [unittest](https://docs.python.org/3/library/unittest.html) (standard library)
+- [unittest.mock](https://docs.python.org/3/library/unittest.mock.html) (standard library)
+- [coverage.py](https://coverage.readthedocs.io/en/stable/)
+
+To ensure the results you obtain on your personal machine are comparable to those generated in the Azure pipeline, please make sure to run your tests with the virtual environment defined by our [Pipfile](/Pipfile). To run your tests with `pipenv`, we've provided two "scripts" shortcuts:
+
+- `pipenv run test` will run `unittest` with `coverage.py`
+- `pipenv run test path/to/test.py` will run a specific test.
+- `pipenv run report` will generate a coverage report of the tests you've run with `pipenv run test`. If you append the `-m` flag to this command, the report will include the lines and branches not covered by tests in addition to the test coverage report.
+
+If you want a coverage report, make sure to run the tests with `pipenv run test` *first*.
+
+## Writing tests
+
+Since consistency is an important consideration for collaborative projects, we have written some guidelines on writing tests for the bot. In addition to these guidelines, it's a good idea to look at the existing code base for examples (e.g., [`test_converters.py`](/tests/bot/test_converters.py)).
+
+### File and directory structure
+
+To organize our test suite, we have chosen to mirror the directory structure of [`bot`](/bot/) in the [`tests`](/tests/) subdirectory. This makes it easy to find the relevant tests by providing a natural grouping of files. More general testing files, such as [`helpers.py`](/tests/helpers.py) are located directly in the `tests` subdirectory.
+
+All files containing tests should have a filename starting with `test_` to make sure `unittest` will discover them. This prefix is typically followed by the name of the file the tests are written for. If needed, a test file can contain multiple test classes, both to provide structure and to be able to provide different fixtures/set-up methods for different groups of tests.
+
+### Writing independent tests
+
+When writing unit tests, it's really important to make sure that each test that you write runs independently from all of the other tests. This both means that the code you write for one test shouldn't influence the result of another test and that if one tests fails, the other tests should still run.
+
+The basis for this is that when you write a test method, it should really only test a single aspect of the thing you're testing. This often means that you do not write one large test that tests "everything" that can be tested for a function, but rather that you write multiple smaller tests that each test a specific branch/path/condition of the function under scrutiny.
+
+To make sure you're not repeating the same set-up steps in all these smaller tests, `unittest` provides fixtures that are executed before and after each test is run. In addition to test fixtures, it also provides special set-up and clean-up methods that are run before the first test in a test class or after the last test of that class has been run. For more information, see the documentation for [`unittest.TestCase`](https://docs.python.org/3/library/unittest.html#unittest.TestCase).
+
+#### Method names and docstrings
+
+As you can probably imagine, writing smaller, independent tests also results in a large number of tests. To make sure that it's easy to see which test does what, it is incredibly important to use good method names to identify what each test is doing. A general guideline is that the name should capture the goal of your test: What is this test method trying to assert?
+
+In addition to good method names, it's also really important to write a good *single-line* docstring. The `unittest` module will print such a single-line docstring along with the method name in the output it gives when a test fails. This means that a good docstring that really captures the purpose of the test makes it much easier to quickly make sense of output.
+
+#### Using self.subTest for independent subtests
+
+Another thing that you will probably encounter is that you want to test a function against a list of input and output values. Given the section on writing independent tests, you may now be tempted to copy-paste the same test method over and over again, once for each unique value that you want to test. However, that would result in a lot of duplicate code that is hard to maintain.
+
+Luckily, `unittest` provides a good alternative to that: the [`subTest`](https://docs.python.org/3/library/unittest.html#distinguishing-test-iterations-using-subtests) context manager. This method is often used in conjunction with a `for`-loop iterating of a collection of values that we want to test a function against and it provides two important features. First, it will make sure that if an assertion statements fails on one of the iterations, the other iterations are still run. The other important feature it provides is that it will distinguish the iterations from each other in the output.
+
+This is an example of `TestCase.subTest` in action (taken from [`test_converters.py`](/tests/bot/test_converters.py)):
+
+```py
+    def test_tag_content_converter_for_valid(self):
+        """TagContentConverter should return correct values for valid input."""
+        test_values = (
+            ('hello', 'hellpo'),
+            ('  h ello  ', 'h ello'),
+        )
+
+        for content, expected_conversion in test_values:
+            with self.subTest(content=content, expected_conversion=expected_conversion):
+                conversion = asyncio.run(TagContentConverter.convert(self.context, content))
+                self.assertEqual(conversion, expected_conversion)
+```
+
+It's important to note the keyword arguments we provide to the `self.subTest` context manager: These keyword arguments and their values will printed in the output when one of the subtests fail, making sure we know *which* subTest failed:
+
+```
+....................................................................
+======================================================================
+FAIL: test_tag_content_converter_for_valid (tests.bot.test_converters.ConverterTests) (content='hello', expected_conversion='hellpo')
+TagContentConverter should return correct values for valid input.
+----------------------------------------------------------------------
+
+# ...
+```
+
+## Mocking
+
+As we are trying to test our "units" of code independently, we want to make sure that we do not rely objects and data generated by "external" code. If we we did, then we wouldn't know if the failure we're observing was caused by the code we are actually trying to test or something external to it.
+
+
+However, the features that we are trying to test often depend on those objects generated by external pieces of code. It would be difficult to test a bot command without having access to a `Context` instance. Fortunately, there's a solution for that: we use fake objects that act like the true object. We call these fake objects "mocks". 
+
+To create these mock object, we mainly use the [`unittest.mock`](https://docs.python.org/3/library/unittest.mock.html) module. In addition, we have also defined a couple of specialized mock objects that mock specific `discord.py` types (see the section on the below.).
+
+An example of mocking is when we provide a command with a mocked version of `discord.ext.commands.Context` object instead of a real `Context` object. This makes sure we can then check (_assert_) if the `send` method of the mocked Context object was called with the correct message content (without having to send a real message to the Discord API!):
+
+```py
+import asyncio
+import unittest
+
+from bot.cogs import bot
+from tests.helpers import MockBot, MockContext
+
+
+class BotCogTests(unittest.TestCase):
+    def test_echo_command_correctly_echoes_arguments(self):
+        """Test if the `!echo <text>` command correctly echoes the content."""
+        mocked_bot = MockBot()
+        bot_cog = bot.Bot(mocked_bot)
+
+        mocked_context = MockContext()
+
+        text = "Hello! This should be echoed!"
+
+        asyncio.run(bot_cog.echo_command.callback(bot_cog, mocked_context, text=text))
+
+        mocked_context.send.assert_called_with(text)
+```
+
+### Mocking coroutines
+
+By default, the `unittest.mock.Mock` and `unittest.mock.MagicMock` classes cannot mock coroutines, since the `__call__` method they provide is synchronous. In anticipation of the `AsyncMock` that will be [introduced in Python 3.8](https://docs.python.org/3.9/whatsnew/3.8.html#unittest), we have added an `AsyncMock` helper to [`helpers.py`](/tests/helpers.py). Do note that this drop-in replacement only implements an asynchronous `__call__` method, not the additional assertions that will come with the new `AsyncMock` type in Python 3.8. 
+
+### Special mocks for some `discord.py` types
+
+To quote Ned Batchelder, Mock objects are "automatic chameleons". This means that they will happily allow the access to any attribute or method and provide a mocked value in return. One downside to this is that if the code you are testing gets the name of the attribute wrong, your mock object will not complain and the test may still pass.
+
+In order to avoid that, we have defined a number of Mock types in [`helpers.py`](/tests/helpers.py) that follow the specifications of the actual Discord types they are mocking. This means that trying to access an attribute or method on a mocked object that does not exist on the equivalent `discord.py` object will result in an `AttributeError`. In addition, these mocks have some sensible defaults and **pass `isinstance` checks for the types they are mocking**. 
+
+These special mocks are added when they are needed, so if you think it would be sensible to add another one, feel free to propose one in your PR.
+
+**Note:** These mock types only "know" the attributes that are set by default when these `discord.py` types are first initialized. If you need to work with dynamically set attributes that are added after initialization, you can still explicitly mock them:
+
+```py
+import unittest.mock
+from tests.helpers import MockGuild
+
+guild = MockGuild()
+guild.some_attribute = unittest.mock.MagicMock()
+```
+
+The attribute `some_attribute` will now be accessible as a `MagicMock` on the mocked object.
+
+---
+
+## Some considerations
+
+Finally, there are some considerations to make when writing tests, both for writing tests in general and for writing tests for our bot in particular.
+
+### Test coverage is a starting point
+
+Having test coverage is a good starting point for unit testing: If a part of your code was not covered by a test, we know that we have not tested it properly. The reverse is unfortunately not true: Even if the code we are testing has 100% branch coverage, it does not mean it's fully tested or guaranteed to work. 
+
+One problem is that 100% branch coverage may be misleading if we haven't tested our code against all the realistic input it may get in production. For instance, take a look at the following `member_information` function and the test we've written for it:
+
+```py
+import datetime
+import unittest
+import unittest.mock
+
+
+def member_information(member):
+    joined = member.joined.stfptime("%d-%m-%Y") if member.joined else "unknown"
+    return f"{member.name} (joined: {joined})"
+
+
+class FunctionsTests(unittest.TestCase):
+    def test_member_information(self):
+        member = unittest.mock.Mock()
+        member.name = "lemon"
+        member.joined = None
+        self.assertEqual(member_information(member), "lemon (joined: unknown)")
+```
+
+If you were to run this test, not only would the function pass the test, `coverage.py` will also tell us that the test provides 100% branch coverage for the function. Can you spot the bug the test suite did not catch?
+
+The problem here is that we have only tested our function with a member object that had `None` for the `member.joined` attribute. This means that `member.joined.stfptime("%d-%m-%Y")` was never executed during our test, leading to us missing the spelling mistake in `stfptime` (it should be `strftime`). 
+
+Adding another test would not increase the test coverage we have, but it does ensure that we'll notice that this function can fail with realistic data:
+
+```py
+# (...)
+class FunctionsTests(unittest.TestCase):
+    # (...)
+    def test_member_information_with_join_datetime(self):
+        member = unittest.mock.Mock()
+        member.name = "lemon"
+        member.joined = datetime.datetime(year=2019, month=10, day=10)
+        self.assertEqual(member_information(member), "lemon (joined: 10-10-2019)")
+```
+
+Output:
+```
+.E
+======================================================================
+ERROR: test_member_information_with_join_datetime (tests.test_functions.FunctionsTests)
+----------------------------------------------------------------------
+Traceback (most recent call last):
+  File "/home/pydis/playground/tests/test_functions.py", line 23, in test_member_information_with_join_datetime
+    self.assertEqual(member_information(member), "lemon (joined: 10-10-2019)")
+  File "/home/pydis/playground/tests/test_functions.py", line 8, in member_information
+    joined = member.joined.stfptime("%d-%m-%Y") if member.joined else "unknown"
+AttributeError: 'datetime.datetime' object has no attribute 'stfptime'
+
+----------------------------------------------------------------------
+Ran 2 tests in 0.003s
+
+FAILED (errors=1)
+```
+
+What's more, even if the spelling mistake would not have been there, the first test did not test if the `member_information` function formatted the `member.join` according to the output we actually want to see.
+
+All in all, it's not only important to consider if all statements or branches were touched at least once with a test, but also if they are extensively tested in all situations that may happen in production.
+
+### Unit Testing vs Integration Testing
+
+Another restriction of unit testing is that it tests, well, in units. Even if we can guarantee that the units work as they should independently, we have no guarantee that they will actually work well together. Even more, while the mocking described above gives us a lot of flexibility in factoring out external code, we are work under the implicit assumption that we fully understand those external parts and utilize it correctly. What if our mocked `Context` object works with a `send` method, but `discord.py` has changed it to a `send_message` method in a recent update? It could mean our tests are passing, but the code it's testing still doesn't work in production.
+
+The answer to this is that we also need to make sure that the individual parts come together into a working application. In addition, we will also need to make sure that the application communicates correctly with external applications. Since we currently have no automated integration tests or functional tests, that means **it's still very important to fire up the bot and test the code you've written manually** in addition to the unit tests you've written.
+
+## Additional resources
+
+* [Ned Batchelder's PyCon talk: Getting Started Testing](https://www.youtube.com/watch?v=FxSsnHeWQBY)
+* [Corey Schafer video about unittest](https://youtu.be/6tNS--WetLI)
+* [RealPython tutorial on unittest testing](https://realpython.com/python-testing/)
+* [RealPython tutorial on mocking](https://realpython.com/python-mock-library/)
diff --git a/tests/__init__.py b/tests/__init__.py
index e69de29bb..2228110ad 100644
--- a/tests/__init__.py
+++ b/tests/__init__.py
@@ -0,0 +1,5 @@
+import logging
+
+
+log = logging.getLogger()
+log.setLevel(logging.CRITICAL)
diff --git a/tests/base.py b/tests/base.py
new file mode 100644
index 000000000..029a249ed
--- /dev/null
+++ b/tests/base.py
@@ -0,0 +1,67 @@
+import logging
+import unittest
+from contextlib import contextmanager
+
+
+class _CaptureLogHandler(logging.Handler):
+    """
+    A logging handler capturing all (raw and formatted) logging output.
+    """
+
+    def __init__(self):
+        super().__init__()
+        self.records = []
+
+    def emit(self, record):
+        self.records.append(record)
+
+
+class LoggingTestCase(unittest.TestCase):
+    """TestCase subclass that adds more logging assertion tools."""
+
+    @contextmanager
+    def assertNotLogs(self, logger=None, level=None, msg=None):
+        """
+        Asserts that no logs of `level` and higher were emitted by `logger`.
+
+        You can specify a specific `logger`, the minimum `logging` level we want to watch and a
+        custom `msg` to be added to the `AssertionError` if thrown. If the assertion fails, the
+        recorded log records will be outputted with the `AssertionError` message. The context
+        manager does not yield a live `look` into the logging records, since we use this context
+        manager when we're testing under the assumption that no log records will be emitted.
+        """
+        if not isinstance(logger, logging.Logger):
+            logger = logging.getLogger(logger)
+
+        if level:
+            level = logging._nameToLevel.get(level, level)
+        else:
+            level = logging.INFO
+
+        handler = _CaptureLogHandler()
+        old_handlers = logger.handlers[:]
+        old_level = logger.level
+        old_propagate = logger.propagate
+
+        logger.handlers = [handler]
+        logger.setLevel(level)
+        logger.propagate = False
+
+        try:
+            yield
+        except Exception as exc:
+            raise exc
+        finally:
+            logger.handlers = old_handlers
+            logger.propagate = old_propagate
+            logger.setLevel(old_level)
+
+        if handler.records:
+            level_name = logging.getLevelName(level)
+            n_logs = len(handler.records)
+            base_message = f"{n_logs} logs of {level_name} or higher were triggered on {logger.name}:\n"
+            records = [str(record) for record in handler.records]
+            record_message = "\n".join(records)
+            standard_message = self._truncateMessage(base_message, record_message)
+            msg = self._formatMessage(msg, standard_message)
+            self.fail(msg)
diff --git a/tests/cogs/__init__.py b/tests/bot/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/cogs/__init__.py
+++ b/tests/bot/__init__.py
diff --git a/tests/cogs/sync/__init__.py b/tests/bot/cogs/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/cogs/sync/__init__.py
+++ b/tests/bot/cogs/__init__.py
diff --git a/tests/rules/__init__.py b/tests/bot/cogs/sync/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/rules/__init__.py
+++ b/tests/bot/cogs/sync/__init__.py
diff --git a/tests/bot/cogs/sync/test_roles.py b/tests/bot/cogs/sync/test_roles.py
new file mode 100644
index 000000000..27ae27639
--- /dev/null
+++ b/tests/bot/cogs/sync/test_roles.py
@@ -0,0 +1,126 @@
+import unittest
+
+from bot.cogs.sync.syncers import Role, get_roles_for_sync
+
+
+class GetRolesForSyncTests(unittest.TestCase):
+    """Tests constructing the roles to synchronize with the site."""
+
+    def test_get_roles_for_sync_empty_return_for_equal_roles(self):
+        """No roles should be synced when no diff is found."""
+        api_roles = {Role(id=41, name='name', colour=33, permissions=0x8, position=1)}
+        guild_roles = {Role(id=41, name='name', colour=33, permissions=0x8, position=1)}
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (set(), set(), set())
+        )
+
+    def test_get_roles_for_sync_returns_roles_to_update_with_non_id_diff(self):
+        """Roles to be synced are returned when non-ID attributes differ."""
+        api_roles = {Role(id=41, name='old name', colour=35, permissions=0x8, position=1)}
+        guild_roles = {Role(id=41, name='new name', colour=33, permissions=0x8, position=2)}
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (set(), guild_roles, set())
+        )
+
+    def test_get_roles_only_returns_roles_that_require_update(self):
+        """Roles that require an update should be returned as the second tuple element."""
+        api_roles = {
+            Role(id=41, name='old name', colour=33, permissions=0x8, position=1),
+            Role(id=53, name='other role', colour=55, permissions=0, position=3)
+        }
+        guild_roles = {
+            Role(id=41, name='new name', colour=35, permissions=0x8, position=2),
+            Role(id=53, name='other role', colour=55, permissions=0, position=3)
+        }
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (
+                set(),
+                {Role(id=41, name='new name', colour=35, permissions=0x8, position=2)},
+                set(),
+            )
+        )
+
+    def test_get_roles_returns_new_roles_in_first_tuple_element(self):
+        """Newly created roles are returned as the first tuple element."""
+        api_roles = {
+            Role(id=41, name='name', colour=35, permissions=0x8, position=1),
+        }
+        guild_roles = {
+            Role(id=41, name='name', colour=35, permissions=0x8, position=1),
+            Role(id=53, name='other role', colour=55, permissions=0, position=2)
+        }
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (
+                {Role(id=53, name='other role', colour=55, permissions=0, position=2)},
+                set(),
+                set(),
+            )
+        )
+
+    def test_get_roles_returns_roles_to_update_and_new_roles(self):
+        """Newly created and updated roles should be returned together."""
+        api_roles = {
+            Role(id=41, name='old name', colour=35, permissions=0x8, position=1),
+        }
+        guild_roles = {
+            Role(id=41, name='new name', colour=40, permissions=0x16, position=2),
+            Role(id=53, name='other role', colour=55, permissions=0, position=3)
+        }
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (
+                {Role(id=53, name='other role', colour=55, permissions=0, position=3)},
+                {Role(id=41, name='new name', colour=40, permissions=0x16, position=2)},
+                set(),
+            )
+        )
+
+    def test_get_roles_returns_roles_to_delete(self):
+        """Roles to be deleted should be returned as the third tuple element."""
+        api_roles = {
+            Role(id=41, name='name', colour=35, permissions=0x8, position=1),
+            Role(id=61, name='to delete', colour=99, permissions=0x9, position=2),
+        }
+        guild_roles = {
+            Role(id=41, name='name', colour=35, permissions=0x8, position=1),
+        }
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (
+                set(),
+                set(),
+                {Role(id=61, name='to delete', colour=99, permissions=0x9, position=2)},
+            )
+        )
+
+    def test_get_roles_returns_roles_to_delete_update_and_new_roles(self):
+        """When roles were added, updated, and removed, all of them are returned properly."""
+        api_roles = {
+            Role(id=41, name='not changed', colour=35, permissions=0x8, position=1),
+            Role(id=61, name='to delete', colour=99, permissions=0x9, position=2),
+            Role(id=71, name='to update', colour=99, permissions=0x9, position=3),
+        }
+        guild_roles = {
+            Role(id=41, name='not changed', colour=35, permissions=0x8, position=1),
+            Role(id=81, name='to create', colour=99, permissions=0x9, position=4),
+            Role(id=71, name='updated', colour=101, permissions=0x5, position=3),
+        }
+
+        self.assertEqual(
+            get_roles_for_sync(guild_roles, api_roles),
+            (
+                {Role(id=81, name='to create', colour=99, permissions=0x9, position=4)},
+                {Role(id=71, name='updated', colour=101, permissions=0x5, position=3)},
+                {Role(id=61, name='to delete', colour=99, permissions=0x9, position=2)},
+            )
+        )
diff --git a/tests/bot/cogs/sync/test_users.py b/tests/bot/cogs/sync/test_users.py
new file mode 100644
index 000000000..ccaf67490
--- /dev/null
+++ b/tests/bot/cogs/sync/test_users.py
@@ -0,0 +1,84 @@
+import unittest
+
+from bot.cogs.sync.syncers import User, get_users_for_sync
+
+
+def fake_user(**kwargs):
+    kwargs.setdefault('id', 43)
+    kwargs.setdefault('name', 'bob the test man')
+    kwargs.setdefault('discriminator', 1337)
+    kwargs.setdefault('avatar_hash', None)
+    kwargs.setdefault('roles', (666,))
+    kwargs.setdefault('in_guild', True)
+    return User(**kwargs)
+
+
+class GetUsersForSyncTests(unittest.TestCase):
+    """Tests constructing the users to synchronize with the site."""
+
+    def test_get_users_for_sync_returns_nothing_for_empty_params(self):
+        """When no users are given, none are returned."""
+        self.assertEqual(
+            get_users_for_sync({}, {}),
+            (set(), set())
+        )
+
+    def test_get_users_for_sync_returns_nothing_for_equal_users(self):
+        """When no users are updated, none are returned."""
+        api_users = {43: fake_user()}
+        guild_users = {43: fake_user()}
+
+        self.assertEqual(
+            get_users_for_sync(guild_users, api_users),
+            (set(), set())
+        )
+
+    def test_get_users_for_sync_returns_users_to_update_on_non_id_field_diff(self):
+        """When a non-ID-field differs, the user to update is returned."""
+        api_users = {43: fake_user()}
+        guild_users = {43: fake_user(name='new fancy name')}
+
+        self.assertEqual(
+            get_users_for_sync(guild_users, api_users),
+            (set(), {fake_user(name='new fancy name')})
+        )
+
+    def test_get_users_for_sync_returns_users_to_create_with_new_ids_on_guild(self):
+        """When new users join the guild, they are returned as the first tuple element."""
+        api_users = {43: fake_user()}
+        guild_users = {43: fake_user(), 63: fake_user(id=63)}
+
+        self.assertEqual(
+            get_users_for_sync(guild_users, api_users),
+            ({fake_user(id=63)}, set())
+        )
+
+    def test_get_users_for_sync_updates_in_guild_field_on_user_leave(self):
+        """When a user leaves the guild, the `in_guild` flag is updated to `False`."""
+        api_users = {43: fake_user(), 63: fake_user(id=63)}
+        guild_users = {43: fake_user()}
+
+        self.assertEqual(
+            get_users_for_sync(guild_users, api_users),
+            (set(), {fake_user(id=63, in_guild=False)})
+        )
+
+    def test_get_users_for_sync_updates_and_creates_users_as_needed(self):
+        """When one user left and another one was updated, both are returned."""
+        api_users = {43: fake_user()}
+        guild_users = {63: fake_user(id=63)}
+
+        self.assertEqual(
+            get_users_for_sync(guild_users, api_users),
+            ({fake_user(id=63)}, {fake_user(in_guild=False)})
+        )
+
+    def test_get_users_for_sync_does_not_duplicate_update_users(self):
+        """When the API knows a user the guild doesn't, nothing is performed."""
+        api_users = {43: fake_user(in_guild=False)}
+        guild_users = {}
+
+        self.assertEqual(
+            get_users_for_sync(guild_users, api_users),
+            (set(), set())
+        )
diff --git a/tests/bot/cogs/test_antispam.py b/tests/bot/cogs/test_antispam.py
new file mode 100644
index 000000000..ce5472c71
--- /dev/null
+++ b/tests/bot/cogs/test_antispam.py
@@ -0,0 +1,35 @@
+import unittest
+
+from bot.cogs import antispam
+
+
+class AntispamConfigurationValidationTests(unittest.TestCase):
+    """Tests validation of the antispam cog configuration."""
+
+    def test_default_antispam_config_is_valid(self):
+        """The default antispam configuration is valid."""
+        validation_errors = antispam.validate_config()
+        self.assertEqual(validation_errors, {})
+
+    def test_unknown_rule_returns_error(self):
+        """Configuring an unknown rule returns an error."""
+        self.assertEqual(
+            antispam.validate_config({'invalid-rule': {}}),
+            {'invalid-rule': "`invalid-rule` is not recognized as an antispam rule."}
+        )
+
+    def test_missing_keys_returns_error(self):
+        """Not configuring required keys returns an error."""
+        keys = (('interval', 'max'), ('max', 'interval'))
+        for configured_key, unconfigured_key in keys:
+            with self.subTest(
+                configured_key=configured_key,
+                unconfigured_key=unconfigured_key
+            ):
+                config = {'burst': {configured_key: 10}}
+                error = f"Key `{unconfigured_key}` is required but not set for rule `burst`"
+
+                self.assertEqual(
+                    antispam.validate_config(config),
+                    {'burst': error}
+                )
diff --git a/tests/bot/cogs/test_duck_pond.py b/tests/bot/cogs/test_duck_pond.py
new file mode 100644
index 000000000..d07b2bce1
--- /dev/null
+++ b/tests/bot/cogs/test_duck_pond.py
@@ -0,0 +1,584 @@
+import asyncio
+import logging
+import typing
+import unittest
+from unittest.mock import MagicMock, patch
+
+import discord
+
+from bot import constants
+from bot.cogs import duck_pond
+from tests import base
+from tests import helpers
+
+MODULE_PATH = "bot.cogs.duck_pond"
+
+
+class DuckPondTests(base.LoggingTestCase):
+    """Tests for DuckPond functionality."""
+
+    @classmethod
+    def setUpClass(cls):
+        """Sets up the objects that only have to be initialized once."""
+        cls.nonstaff_member = helpers.MockMember(name="Non-staffer")
+
+        cls.staff_role = helpers.MockRole(name="Staff role", id=constants.STAFF_ROLES[0])
+        cls.staff_member = helpers.MockMember(name="staffer", roles=[cls.staff_role])
+
+        cls.checkmark_emoji = "\N{White Heavy Check Mark}"
+        cls.thumbs_up_emoji = "\N{Thumbs Up Sign}"
+        cls.unicode_duck_emoji = "\N{Duck}"
+        cls.duck_pond_emoji = helpers.MockPartialEmoji(id=constants.DuckPond.custom_emojis[0])
+        cls.non_duck_custom_emoji = helpers.MockPartialEmoji(id=123)
+
+    def setUp(self):
+        """Sets up the objects that need to be refreshed before each test."""
+        self.bot = helpers.MockBot(user=helpers.MockMember(id=46692))
+        self.cog = duck_pond.DuckPond(bot=self.bot)
+
+    def test_duck_pond_correctly_initializes(self):
+        """`__init__ should set `bot` and `webhook_id` attributes and schedule `fetch_webhook`."""
+        bot = helpers.MockBot()
+        cog = MagicMock()
+
+        duck_pond.DuckPond.__init__(cog, bot)
+
+        self.assertEqual(cog.bot, bot)
+        self.assertEqual(cog.webhook_id, constants.Webhooks.duck_pond)
+        bot.loop.create_loop.called_once_with(cog.fetch_webhook())
+
+    def test_fetch_webhook_succeeds_without_connectivity_issues(self):
+        """The `fetch_webhook` method waits until `READY` event and sets the `webhook` attribute."""
+        self.bot.fetch_webhook.return_value = "dummy webhook"
+        self.cog.webhook_id = 1
+
+        asyncio.run(self.cog.fetch_webhook())
+
+        self.bot.wait_until_ready.assert_called_once()
+        self.bot.fetch_webhook.assert_called_once_with(1)
+        self.assertEqual(self.cog.webhook, "dummy webhook")
+
+    def test_fetch_webhook_logs_when_unable_to_fetch_webhook(self):
+        """The `fetch_webhook` method should log an exception when it fails to fetch the webhook."""
+        self.bot.fetch_webhook.side_effect = discord.HTTPException(response=MagicMock(), message="Not found.")
+        self.cog.webhook_id = 1
+
+        log = logging.getLogger('bot.cogs.duck_pond')
+        with self.assertLogs(logger=log, level=logging.ERROR) as log_watcher:
+            asyncio.run(self.cog.fetch_webhook())
+
+        self.bot.wait_until_ready.assert_called_once()
+        self.bot.fetch_webhook.assert_called_once_with(1)
+
+        self.assertEqual(len(log_watcher.records), 1)
+
+        record = log_watcher.records[0]
+        self.assertEqual(record.levelno, logging.ERROR)
+
+    def test_is_staff_returns_correct_values_based_on_instance_passed(self):
+        """The `is_staff` method should return correct values based on the instance passed."""
+        test_cases = (
+            (helpers.MockUser(name="User instance"), False),
+            (helpers.MockMember(name="Member instance without staff role"), False),
+            (helpers.MockMember(name="Member instance with staff role", roles=[self.staff_role]), True)
+        )
+
+        for user, expected_return in test_cases:
+            actual_return = self.cog.is_staff(user)
+            with self.subTest(user_type=user.name, expected_return=expected_return, actual_return=actual_return):
+                self.assertEqual(expected_return, actual_return)
+
+    @helpers.async_test
+    async def test_has_green_checkmark_correctly_detects_presence_of_green_checkmark_emoji(self):
+        """The `has_green_checkmark` method should only return `True` if one is present."""
+        test_cases = (
+            (
+                "No reactions", helpers.MockMessage(), False
+            ),
+            (
+                "No green check mark reactions",
+                helpers.MockMessage(reactions=[
+                    helpers.MockReaction(emoji=self.unicode_duck_emoji, users=[self.bot.user]),
+                    helpers.MockReaction(emoji=self.thumbs_up_emoji, users=[self.bot.user])
+                ]),
+                False
+            ),
+            (
+                "Green check mark reaction, but not from our bot",
+                helpers.MockMessage(reactions=[
+                    helpers.MockReaction(emoji=self.unicode_duck_emoji, users=[self.bot.user]),
+                    helpers.MockReaction(emoji=self.checkmark_emoji, users=[self.staff_member])
+                ]),
+                False
+            ),
+            (
+                "Green check mark reaction, with one from the bot",
+                helpers.MockMessage(reactions=[
+                    helpers.MockReaction(emoji=self.unicode_duck_emoji, users=[self.bot.user]),
+                    helpers.MockReaction(emoji=self.checkmark_emoji, users=[self.staff_member, self.bot.user])
+                ]),
+                True
+            )
+        )
+
+        for description, message, expected_return in test_cases:
+            actual_return = await self.cog.has_green_checkmark(message)
+            with self.subTest(
+                test_case=description,
+                expected_return=expected_return,
+                actual_return=actual_return
+            ):
+                self.assertEqual(expected_return, actual_return)
+
+    def test_send_webhook_correctly_passes_on_arguments(self):
+        """The `send_webhook` method should pass the arguments to the webhook correctly."""
+        self.cog.webhook = helpers.MockAsyncWebhook()
+
+        content = "fake content"
+        username = "fake username"
+        avatar_url = "fake avatar_url"
+        embed = "fake embed"
+
+        asyncio.run(self.cog.send_webhook(content, username, avatar_url, embed))
+
+        self.cog.webhook.send.assert_called_once_with(
+            content=content,
+            username=username,
+            avatar_url=avatar_url,
+            embed=embed
+        )
+
+    def test_send_webhook_logs_when_sending_message_fails(self):
+        """The `send_webhook` method should catch a `discord.HTTPException` and log accordingly."""
+        self.cog.webhook = helpers.MockAsyncWebhook()
+        self.cog.webhook.send.side_effect = discord.HTTPException(response=MagicMock(), message="Something failed.")
+
+        log = logging.getLogger('bot.cogs.duck_pond')
+        with self.assertLogs(logger=log, level=logging.ERROR) as log_watcher:
+            asyncio.run(self.cog.send_webhook())
+
+        self.assertEqual(len(log_watcher.records), 1)
+
+        record = log_watcher.records[0]
+        self.assertEqual(record.levelno, logging.ERROR)
+
+    def _get_reaction(
+        self,
+        emoji: typing.Union[str, helpers.MockEmoji],
+        staff: int = 0,
+        nonstaff: int = 0
+    ) -> helpers.MockReaction:
+        staffers = [helpers.MockMember(roles=[self.staff_role]) for _ in range(staff)]
+        nonstaffers = [helpers.MockMember() for _ in range(nonstaff)]
+        return helpers.MockReaction(emoji=emoji, users=staffers + nonstaffers)
+
+    @helpers.async_test
+    async def test_count_ducks_correctly_counts_the_number_of_eligible_duck_emojis(self):
+        """The `count_ducks` method should return the number of unique staffers who gave a duck."""
+        test_cases = (
+            # Simple test cases
+            # A message without reactions should return 0
+            (
+                "No reactions",
+                helpers.MockMessage(),
+                0
+            ),
+            # A message with a non-duck reaction from a non-staffer should return 0
+            (
+                "Non-duck reaction from non-staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.thumbs_up_emoji, nonstaff=1)]),
+                0
+            ),
+            # A message with a non-duck reaction from a staffer should return 0
+            (
+                "Non-duck reaction from staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.non_duck_custom_emoji, staff=1)]),
+                0
+            ),
+            # A message with a non-duck reaction from a non-staffer and staffer should return 0
+            (
+                "Non-duck reaction from staffer + non-staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.thumbs_up_emoji, staff=1, nonstaff=1)]),
+                0
+            ),
+            # A message with a unicode duck reaction from a non-staffer should return 0
+            (
+                "Unicode Duck Reaction from non-staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.unicode_duck_emoji, nonstaff=1)]),
+                0
+            ),
+            # A message with a unicode duck reaction from a staffer should return 1
+            (
+                "Unicode Duck Reaction from staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.unicode_duck_emoji, staff=1)]),
+                1
+            ),
+            # A message with a unicode duck reaction from a non-staffer and staffer should return 1
+            (
+                "Unicode Duck Reaction from staffer + non-staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.unicode_duck_emoji, staff=1, nonstaff=1)]),
+                1
+            ),
+            # A message with a duckpond duck reaction from a non-staffer should return 0
+            (
+                "Duckpond Duck Reaction from non-staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.duck_pond_emoji, nonstaff=1)]),
+                0
+            ),
+            # A message with a duckpond duck reaction from a staffer should return 1
+            (
+                "Duckpond Duck Reaction from staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.duck_pond_emoji, staff=1)]),
+                1
+            ),
+            # A message with a duckpond duck reaction from a non-staffer and staffer should return 1
+            (
+                "Duckpond Duck Reaction from staffer + non-staffer",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.duck_pond_emoji, staff=1, nonstaff=1)]),
+                1
+            ),
+
+            # Complex test cases
+            # A message with duckpond duck reactions from 3 staffers and 2 non-staffers returns 3
+            (
+                "Duckpond Duck Reaction from 3 staffers + 2 non-staffers",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=self.duck_pond_emoji, staff=3, nonstaff=2)]),
+                3
+            ),
+            # A staffer with multiple duck reactions only counts once
+            (
+                "Two different duck reactions from the same staffer",
+                helpers.MockMessage(
+                    reactions=[
+                        helpers.MockReaction(emoji=self.duck_pond_emoji, users=[self.staff_member]),
+                        helpers.MockReaction(emoji=self.unicode_duck_emoji, users=[self.staff_member]),
+                    ]
+                ),
+                1
+            ),
+            # A non-string emoji does not count (to test the `isinstance(reaction.emoji, str)` elif)
+            (
+                "Reaction with non-Emoji/str emoij from 3 staffers + 2 non-staffers",
+                helpers.MockMessage(reactions=[self._get_reaction(emoji=100, staff=3, nonstaff=2)]),
+                0
+            ),
+            # We correctly sum when multiple reactions are provided.
+            (
+                "Duckpond Duck Reaction from 3 staffers + 2 non-staffers",
+                helpers.MockMessage(
+                    reactions=[
+                        self._get_reaction(emoji=self.duck_pond_emoji, staff=3, nonstaff=2),
+                        self._get_reaction(emoji=self.unicode_duck_emoji, staff=4, nonstaff=9),
+                    ]
+                ),
+                3 + 4
+            ),
+        )
+
+        for description, message, expected_count in test_cases:
+            actual_count = await self.cog.count_ducks(message)
+            with self.subTest(test_case=description, expected_count=expected_count, actual_count=actual_count):
+                self.assertEqual(expected_count, actual_count)
+
+    @helpers.async_test
+    async def test_relay_message_correctly_relays_content_and_attachments(self):
+        """The `relay_message` method should correctly relay message content and attachments."""
+        send_webhook_path = f"{MODULE_PATH}.DuckPond.send_webhook"
+        send_attachments_path = f"{MODULE_PATH}.send_attachments"
+
+        self.cog.webhook = helpers.MockAsyncWebhook()
+
+        test_values = (
+            (helpers.MockMessage(clean_content="", attachments=[]), False, False),
+            (helpers.MockMessage(clean_content="message", attachments=[]), True, False),
+            (helpers.MockMessage(clean_content="", attachments=["attachment"]), False, True),
+            (helpers.MockMessage(clean_content="message", attachments=["attachment"]), True, True),
+        )
+
+        for message, expect_webhook_call, expect_attachment_call in test_values:
+            with patch(send_webhook_path, new_callable=helpers.AsyncMock) as send_webhook:
+                with patch(send_attachments_path, new_callable=helpers.AsyncMock) as send_attachments:
+                    with self.subTest(clean_content=message.clean_content, attachments=message.attachments):
+                        await self.cog.relay_message(message)
+
+                        self.assertEqual(expect_webhook_call, send_webhook.called)
+                        self.assertEqual(expect_attachment_call, send_attachments.called)
+
+                        message.add_reaction.assert_called_once_with(self.checkmark_emoji)
+
+    @patch(f"{MODULE_PATH}.send_attachments", new_callable=helpers.AsyncMock)
+    @helpers.async_test
+    async def test_relay_message_handles_irretrievable_attachment_exceptions(self, send_attachments):
+        """The `relay_message` method should handle irretrievable attachments."""
+        message = helpers.MockMessage(clean_content="message", attachments=["attachment"])
+        side_effects = (discord.errors.Forbidden(MagicMock(), ""), discord.errors.NotFound(MagicMock(), ""))
+
+        self.cog.webhook = helpers.MockAsyncWebhook()
+        log = logging.getLogger("bot.cogs.duck_pond")
+
+        for side_effect in side_effects:
+            send_attachments.side_effect = side_effect
+            with patch(f"{MODULE_PATH}.DuckPond.send_webhook", new_callable=helpers.AsyncMock) as send_webhook:
+                with self.subTest(side_effect=type(side_effect).__name__):
+                    with self.assertNotLogs(logger=log, level=logging.ERROR):
+                        await self.cog.relay_message(message)
+
+                    self.assertEqual(send_webhook.call_count, 2)
+
+    @patch(f"{MODULE_PATH}.DuckPond.send_webhook", new_callable=helpers.AsyncMock)
+    @patch(f"{MODULE_PATH}.send_attachments", new_callable=helpers.AsyncMock)
+    @helpers.async_test
+    async def test_relay_message_handles_attachment_http_error(self, send_attachments, send_webhook):
+        """The `relay_message` method should handle irretrievable attachments."""
+        message = helpers.MockMessage(clean_content="message", attachments=["attachment"])
+
+        self.cog.webhook = helpers.MockAsyncWebhook()
+        log = logging.getLogger("bot.cogs.duck_pond")
+
+        side_effect = discord.HTTPException(MagicMock(), "")
+        send_attachments.side_effect = side_effect
+        with self.subTest(side_effect=type(side_effect).__name__):
+            with self.assertLogs(logger=log, level=logging.ERROR) as log_watcher:
+                await self.cog.relay_message(message)
+
+            send_webhook.assert_called_once_with(
+                content=message.clean_content,
+                username=message.author.display_name,
+                avatar_url=message.author.avatar_url
+            )
+
+            self.assertEqual(len(log_watcher.records), 1)
+
+            record = log_watcher.records[0]
+            self.assertEqual(record.levelno, logging.ERROR)
+
+    def _mock_payload(self, label: str, is_custom_emoji: bool, id_: int, emoji_name: str):
+        """Creates a mock `on_raw_reaction_add` payload with the specified emoji data."""
+        payload = MagicMock(name=label)
+        payload.emoji.is_custom_emoji.return_value = is_custom_emoji
+        payload.emoji.id = id_
+        payload.emoji.name = emoji_name
+        return payload
+
+    @helpers.async_test
+    async def test_payload_has_duckpond_emoji_correctly_detects_relevant_emojis(self):
+        """The `on_raw_reaction_add` event handler should ignore irrelevant emojis."""
+        test_values = (
+            # Custom Emojis
+            (
+                self._mock_payload(
+                    label="Custom Duckpond Emoji",
+                    is_custom_emoji=True,
+                    id_=constants.DuckPond.custom_emojis[0],
+                    emoji_name=""
+                ),
+                True
+            ),
+            (
+                self._mock_payload(
+                    label="Custom Non-Duckpond Emoji",
+                    is_custom_emoji=True,
+                    id_=123,
+                    emoji_name=""
+                ),
+                False
+            ),
+            # Unicode Emojis
+            (
+                self._mock_payload(
+                    label="Unicode Duck Emoji",
+                    is_custom_emoji=False,
+                    id_=1,
+                    emoji_name=self.unicode_duck_emoji
+                ),
+                True
+            ),
+            (
+                self._mock_payload(
+                    label="Unicode Non-Duck Emoji",
+                    is_custom_emoji=False,
+                    id_=1,
+                    emoji_name=self.thumbs_up_emoji
+                ),
+                False
+            ),
+        )
+
+        for payload, expected_return in test_values:
+            actual_return = self.cog._payload_has_duckpond_emoji(payload)
+            with self.subTest(case=payload._mock_name, expected_return=expected_return, actual_return=actual_return):
+                self.assertEqual(expected_return, actual_return)
+
+    @patch(f"{MODULE_PATH}.discord.utils.get")
+    @patch(f"{MODULE_PATH}.DuckPond._payload_has_duckpond_emoji", new=MagicMock(return_value=False))
+    def test_on_raw_reaction_add_returns_early_with_payload_without_duck_emoji(self, utils_get):
+        """The `on_raw_reaction_add` method should return early if the payload does not contain a duck emoji."""
+        self.assertIsNone(asyncio.run(self.cog.on_raw_reaction_add(payload=MagicMock())))
+
+        # Ensure we've returned before making an unnecessary API call in the lines of code after the emoji check
+        utils_get.assert_not_called()
+
+    def _raw_reaction_mocks(self, channel_id, message_id, user_id):
+        """Sets up mocks for tests of the `on_raw_reaction_add` event listener."""
+        channel = helpers.MockTextChannel(id=channel_id)
+        self.bot.get_all_channels.return_value = (channel,)
+
+        message = helpers.MockMessage(id=message_id)
+
+        channel.fetch_message.return_value = message
+
+        member = helpers.MockMember(id=user_id, roles=[self.staff_role])
+        message.guild.members = (member,)
+
+        payload = MagicMock(channel_id=channel_id, message_id=message_id, user_id=user_id)
+
+        return channel, message, member, payload
+
+    @helpers.async_test
+    async def test_on_raw_reaction_add_returns_for_bot_and_non_staff_members(self):
+        """The `on_raw_reaction_add` event handler should return for bot users or non-staff members."""
+        channel_id = 1234
+        message_id = 2345
+        user_id = 3456
+
+        channel, message, _, payload = self._raw_reaction_mocks(channel_id, message_id, user_id)
+
+        test_cases = (
+            ("non-staff member", helpers.MockMember(id=user_id)),
+            ("bot staff member", helpers.MockMember(id=user_id, roles=[self.staff_role], bot=True)),
+        )
+
+        payload.emoji = self.duck_pond_emoji
+
+        for description, member in test_cases:
+            message.guild.members = (member, )
+            with self.subTest(test_case=description), patch(f"{MODULE_PATH}.DuckPond.has_green_checkmark") as checkmark:
+                checkmark.side_effect = AssertionError(
+                    "Expected method to return before calling `self.has_green_checkmark`."
+                )
+                self.assertIsNone(await self.cog.on_raw_reaction_add(payload))
+
+                # Check that we did make it past the payload checks
+                channel.fetch_message.assert_called_once()
+                channel.fetch_message.reset_mock()
+
+    @patch(f"{MODULE_PATH}.DuckPond.is_staff")
+    @patch(f"{MODULE_PATH}.DuckPond.count_ducks", new_callable=helpers.AsyncMock)
+    def test_on_raw_reaction_add_returns_on_message_with_green_checkmark_placed_by_bot(self, count_ducks, is_staff):
+        """The `on_raw_reaction_add` event should return when the message has a green check mark placed by the bot."""
+        channel_id = 31415926535
+        message_id = 27182818284
+        user_id = 16180339887
+
+        channel, message, member, payload = self._raw_reaction_mocks(channel_id, message_id, user_id)
+
+        payload.emoji = helpers.MockPartialEmoji(name=self.unicode_duck_emoji)
+        payload.emoji.is_custom_emoji.return_value = False
+
+        message.reactions = [helpers.MockReaction(emoji=self.checkmark_emoji, users=[self.bot.user])]
+
+        is_staff.return_value = True
+        count_ducks.side_effect = AssertionError("Expected method to return before calling `self.count_ducks`")
+
+        self.assertIsNone(asyncio.run(self.cog.on_raw_reaction_add(payload)))
+
+        # Assert that we've made it past `self.is_staff`
+        is_staff.assert_called_once()
+
+    @helpers.async_test
+    async def test_on_raw_reaction_add_does_not_relay_below_duck_threshold(self):
+        """The `on_raw_reaction_add` listener should not relay messages or attachments below the duck threshold."""
+        test_cases = (
+            (constants.DuckPond.threshold - 1, False),
+            (constants.DuckPond.threshold, True),
+            (constants.DuckPond.threshold + 1, True),
+        )
+
+        channel, message, member, payload = self._raw_reaction_mocks(channel_id=3, message_id=4, user_id=5)
+
+        payload.emoji = self.duck_pond_emoji
+
+        for duck_count, should_relay in test_cases:
+            with patch(f"{MODULE_PATH}.DuckPond.relay_message", new_callable=helpers.AsyncMock) as relay_message:
+                with patch(f"{MODULE_PATH}.DuckPond.count_ducks", new_callable=helpers.AsyncMock) as count_ducks:
+                    count_ducks.return_value = duck_count
+                    with self.subTest(duck_count=duck_count, should_relay=should_relay):
+                        await self.cog.on_raw_reaction_add(payload)
+
+                        # Confirm that we've made it past counting
+                        count_ducks.assert_called_once()
+
+                        # Did we relay a message?
+                        has_relayed = relay_message.called
+                        self.assertEqual(has_relayed, should_relay)
+
+                        if should_relay:
+                            relay_message.assert_called_once_with(message)
+
+    @helpers.async_test
+    async def test_on_raw_reaction_remove_prevents_removal_of_green_checkmark_depending_on_the_duck_count(self):
+        """The `on_raw_reaction_remove` listener prevents removal of the check mark on messages with enough ducks."""
+        checkmark = helpers.MockPartialEmoji(name=self.checkmark_emoji)
+
+        message = helpers.MockMessage(id=1234)
+
+        channel = helpers.MockTextChannel(id=98765)
+        channel.fetch_message.return_value = message
+
+        self.bot.get_all_channels.return_value = (channel, )
+
+        payload = MagicMock(channel_id=channel.id, message_id=message.id, emoji=checkmark)
+
+        test_cases = (
+            (constants.DuckPond.threshold - 1, False),
+            (constants.DuckPond.threshold, True),
+            (constants.DuckPond.threshold + 1, True),
+        )
+        for duck_count, should_re_add_checkmark in test_cases:
+            with patch(f"{MODULE_PATH}.DuckPond.count_ducks", new_callable=helpers.AsyncMock) as count_ducks:
+                count_ducks.return_value = duck_count
+                with self.subTest(duck_count=duck_count, should_re_add_checkmark=should_re_add_checkmark):
+                    await self.cog.on_raw_reaction_remove(payload)
+
+                    # Check if we fetched the message
+                    channel.fetch_message.assert_called_once_with(message.id)
+
+                    # Check if we actually counted the number of ducks
+                    count_ducks.assert_called_once_with(message)
+
+                    has_re_added_checkmark = message.add_reaction.called
+                    self.assertEqual(should_re_add_checkmark, has_re_added_checkmark)
+
+                    if should_re_add_checkmark:
+                        message.add_reaction.assert_called_once_with(self.checkmark_emoji)
+                        message.add_reaction.reset_mock()
+
+                    # reset mocks
+                    channel.fetch_message.reset_mock()
+                    message.reset_mock()
+
+    def test_on_raw_reaction_remove_ignores_removal_of_non_checkmark_reactions(self):
+        """The `on_raw_reaction_remove` listener should ignore the removal of non-check mark emojis."""
+        channel = helpers.MockTextChannel(id=98765)
+
+        channel.fetch_message.side_effect = AssertionError(
+            "Expected method to return before calling `channel.fetch_message`"
+        )
+
+        self.bot.get_all_channels.return_value = (channel, )
+
+        payload = MagicMock(emoji=helpers.MockPartialEmoji(name=self.thumbs_up_emoji), channel_id=channel.id)
+
+        self.assertIsNone(asyncio.run(self.cog.on_raw_reaction_remove(payload)))
+
+        channel.fetch_message.assert_not_called()
+
+
+class DuckPondSetupTests(unittest.TestCase):
+    """Tests setup of the `DuckPond` cog."""
+
+    def test_setup(self):
+        """Setup of the extension should call add_cog."""
+        bot = helpers.MockBot()
+        duck_pond.setup(bot)
+        bot.add_cog.assert_called_once()
diff --git a/tests/bot/cogs/test_information.py b/tests/bot/cogs/test_information.py
new file mode 100644
index 000000000..4496a2ae0
--- /dev/null
+++ b/tests/bot/cogs/test_information.py
@@ -0,0 +1,582 @@
+import asyncio
+import textwrap
+import unittest
+import unittest.mock
+
+import discord
+
+from bot import constants
+from bot.cogs import information
+from bot.decorators import InChannelCheckFailure
+from tests import helpers
+
+
+COG_PATH = "bot.cogs.information.Information"
+
+
+class InformationCogTests(unittest.TestCase):
+    """Tests the Information cog."""
+
+    @classmethod
+    def setUpClass(cls):
+        cls.moderator_role = helpers.MockRole(name="Moderator", id=constants.Roles.moderator)
+
+    def setUp(self):
+        """Sets up fresh objects for each test."""
+        self.bot = helpers.MockBot()
+
+        self.cog = information.Information(self.bot)
+
+        self.ctx = helpers.MockContext()
+        self.ctx.author.roles.append(self.moderator_role)
+
+    def test_roles_command_command(self):
+        """Test if the `role_info` command correctly returns the `moderator_role`."""
+        self.ctx.guild.roles.append(self.moderator_role)
+
+        self.cog.roles_info.can_run = helpers.AsyncMock()
+        self.cog.roles_info.can_run.return_value = True
+
+        coroutine = self.cog.roles_info.callback(self.cog, self.ctx)
+
+        self.assertIsNone(asyncio.run(coroutine))
+        self.ctx.send.assert_called_once()
+
+        _, kwargs = self.ctx.send.call_args
+        embed = kwargs.pop('embed')
+
+        self.assertEqual(embed.title, "Role information")
+        self.assertEqual(embed.colour, discord.Colour.blurple())
+        self.assertEqual(embed.description, f"`{self.moderator_role.id}` - {self.moderator_role.mention}\n")
+        self.assertEqual(embed.footer.text, "Total roles: 1")
+
+    def test_role_info_command(self):
+        """Tests the `role info` command."""
+        dummy_role = helpers.MockRole(
+            name="Dummy",
+            id=112233445566778899,
+            colour=discord.Colour.blurple(),
+            position=10,
+            members=[self.ctx.author],
+            permissions=discord.Permissions(0)
+        )
+
+        admin_role = helpers.MockRole(
+            name="Admins",
+            id=998877665544332211,
+            colour=discord.Colour.red(),
+            position=3,
+            members=[self.ctx.author],
+            permissions=discord.Permissions(0),
+        )
+
+        self.ctx.guild.roles.append([dummy_role, admin_role])
+
+        self.cog.role_info.can_run = helpers.AsyncMock()
+        self.cog.role_info.can_run.return_value = True
+
+        coroutine = self.cog.role_info.callback(self.cog, self.ctx, dummy_role, admin_role)
+
+        self.assertIsNone(asyncio.run(coroutine))
+
+        self.assertEqual(self.ctx.send.call_count, 2)
+
+        (_, dummy_kwargs), (_, admin_kwargs) = self.ctx.send.call_args_list
+
+        dummy_embed = dummy_kwargs["embed"]
+        admin_embed = admin_kwargs["embed"]
+
+        self.assertEqual(dummy_embed.title, "Dummy info")
+        self.assertEqual(dummy_embed.colour, discord.Colour.blurple())
+
+        self.assertEqual(dummy_embed.fields[0].value, str(dummy_role.id))
+        self.assertEqual(dummy_embed.fields[1].value, f"#{dummy_role.colour.value:0>6x}")
+        self.assertEqual(dummy_embed.fields[2].value, "0.63 0.48 218")
+        self.assertEqual(dummy_embed.fields[3].value, "1")
+        self.assertEqual(dummy_embed.fields[4].value, "10")
+        self.assertEqual(dummy_embed.fields[5].value, "0")
+
+        self.assertEqual(admin_embed.title, "Admins info")
+        self.assertEqual(admin_embed.colour, discord.Colour.red())
+
+    @unittest.mock.patch('bot.cogs.information.time_since')
+    def test_server_info_command(self, time_since_patch):
+        time_since_patch.return_value = '2 days ago'
+
+        self.ctx.guild = helpers.MockGuild(
+            features=('lemons', 'apples'),
+            region="The Moon",
+            roles=[self.moderator_role],
+            channels=[
+                discord.TextChannel(
+                    state={},
+                    guild=self.ctx.guild,
+                    data={'id': 42, 'name': 'lemons-offering', 'position': 22, 'type': 'text'}
+                ),
+                discord.CategoryChannel(
+                    state={},
+                    guild=self.ctx.guild,
+                    data={'id': 5125, 'name': 'the-lemon-collection', 'position': 22, 'type': 'category'}
+                ),
+                discord.VoiceChannel(
+                    state={},
+                    guild=self.ctx.guild,
+                    data={'id': 15290, 'name': 'listen-to-lemon', 'position': 22, 'type': 'voice'}
+                )
+            ],
+            members=[
+                *(helpers.MockMember(status='online') for _ in range(2)),
+                *(helpers.MockMember(status='idle') for _ in range(1)),
+                *(helpers.MockMember(status='dnd') for _ in range(4)),
+                *(helpers.MockMember(status='offline') for _ in range(3)),
+            ],
+            member_count=1_234,
+            icon_url='a-lemon.jpg',
+        )
+
+        coroutine = self.cog.server_info.callback(self.cog, self.ctx)
+        self.assertIsNone(asyncio.run(coroutine))
+
+        time_since_patch.assert_called_once_with(self.ctx.guild.created_at, precision='days')
+        _, kwargs = self.ctx.send.call_args
+        embed = kwargs.pop('embed')
+        self.assertEqual(embed.colour, discord.Colour.blurple())
+        self.assertEqual(
+            embed.description,
+            textwrap.dedent(
+                f"""
+                **Server information**
+                Created: {time_since_patch.return_value}
+                Voice region: {self.ctx.guild.region}
+                Features: {', '.join(self.ctx.guild.features)}
+
+                **Counts**
+                Members: {self.ctx.guild.member_count:,}
+                Roles: {len(self.ctx.guild.roles)}
+                Text: 1
+                Voice: 1
+                Channel categories: 1
+
+                **Members**
+                {constants.Emojis.status_online} 2
+                {constants.Emojis.status_idle} 1
+                {constants.Emojis.status_dnd} 4
+                {constants.Emojis.status_offline} 3
+                """
+            )
+        )
+        self.assertEqual(embed.thumbnail.url, 'a-lemon.jpg')
+
+
+class UserInfractionHelperMethodTests(unittest.TestCase):
+    """Tests for the helper methods of the `!user` command."""
+
+    def setUp(self):
+        """Common set-up steps done before for each test."""
+        self.bot = helpers.MockBot()
+        self.bot.api_client.get = helpers.AsyncMock()
+        self.cog = information.Information(self.bot)
+        self.member = helpers.MockMember(id=1234)
+
+    def test_user_command_helper_method_get_requests(self):
+        """The helper methods should form the correct get requests."""
+        test_values = (
+            {
+                "helper_method": self.cog.basic_user_infraction_counts,
+                "expected_args": ("bot/infractions", {'hidden': 'False', 'user__id': str(self.member.id)}),
+            },
+            {
+                "helper_method": self.cog.expanded_user_infraction_counts,
+                "expected_args": ("bot/infractions", {'user__id': str(self.member.id)}),
+            },
+            {
+                "helper_method": self.cog.user_nomination_counts,
+                "expected_args": ("bot/nominations", {'user__id': str(self.member.id)}),
+            },
+        )
+
+        for test_value in test_values:
+            helper_method = test_value["helper_method"]
+            endpoint, params = test_value["expected_args"]
+
+            with self.subTest(method=helper_method, endpoint=endpoint, params=params):
+                asyncio.run(helper_method(self.member))
+                self.bot.api_client.get.assert_called_once_with(endpoint, params=params)
+                self.bot.api_client.get.reset_mock()
+
+    def _method_subtests(self, method, test_values, default_header):
+        """Helper method that runs the subtests for the different helper methods."""
+        for test_value in test_values:
+            api_response = test_value["api response"]
+            expected_lines = test_value["expected_lines"]
+
+            with self.subTest(method=method, api_response=api_response, expected_lines=expected_lines):
+                self.bot.api_client.get.return_value = api_response
+
+                expected_output = "\n".join(default_header + expected_lines)
+                actual_output = asyncio.run(method(self.member))
+
+                self.assertEqual(expected_output, actual_output)
+
+    def test_basic_user_infraction_counts_returns_correct_strings(self):
+        """The method should correctly list both the total and active number of non-hidden infractions."""
+        test_values = (
+            # No infractions means zero counts
+            {
+                "api response": [],
+                "expected_lines": ["Total: 0", "Active: 0"],
+            },
+            # Simple, single-infraction dictionaries
+            {
+                "api response": [{"type": "ban", "active": True}],
+                "expected_lines": ["Total: 1", "Active: 1"],
+            },
+            {
+                "api response": [{"type": "ban", "active": False}],
+                "expected_lines": ["Total: 1", "Active: 0"],
+            },
+            # Multiple infractions with various `active` status
+            {
+                "api response": [
+                    {"type": "ban", "active": True},
+                    {"type": "kick", "active": False},
+                    {"type": "ban", "active": True},
+                    {"type": "ban", "active": False},
+                ],
+                "expected_lines": ["Total: 4", "Active: 2"],
+            },
+        )
+
+        header = ["**Infractions**"]
+
+        self._method_subtests(self.cog.basic_user_infraction_counts, test_values, header)
+
+    def test_expanded_user_infraction_counts_returns_correct_strings(self):
+        """The method should correctly list the total and active number of all infractions split by infraction type."""
+        test_values = (
+            {
+                "api response": [],
+                "expected_lines": ["This user has never received an infraction."],
+            },
+            # Shows non-hidden inactive infraction as expected
+            {
+                "api response": [{"type": "kick", "active": False, "hidden": False}],
+                "expected_lines": ["Kicks: 1"],
+            },
+            # Shows non-hidden active infraction as expected
+            {
+                "api response": [{"type": "mute", "active": True, "hidden": False}],
+                "expected_lines": ["Mutes: 1 (1 active)"],
+            },
+            # Shows hidden inactive infraction as expected
+            {
+                "api response": [{"type": "superstar", "active": False, "hidden": True}],
+                "expected_lines": ["Superstars: 1"],
+            },
+            # Shows hidden active infraction as expected
+            {
+                "api response": [{"type": "ban", "active": True, "hidden": True}],
+                "expected_lines": ["Bans: 1 (1 active)"],
+            },
+            # Correctly displays tally of multiple infractions of mixed properties in alphabetical order
+            {
+                "api response": [
+                    {"type": "kick", "active": False, "hidden": True},
+                    {"type": "ban", "active": True, "hidden": True},
+                    {"type": "superstar", "active": True, "hidden": True},
+                    {"type": "mute", "active": True, "hidden": True},
+                    {"type": "ban", "active": False, "hidden": False},
+                    {"type": "note", "active": False, "hidden": True},
+                    {"type": "note", "active": False, "hidden": True},
+                    {"type": "warn", "active": False, "hidden": False},
+                    {"type": "note", "active": False, "hidden": True},
+                ],
+                "expected_lines": [
+                    "Bans: 2 (1 active)",
+                    "Kicks: 1",
+                    "Mutes: 1 (1 active)",
+                    "Notes: 3",
+                    "Superstars: 1 (1 active)",
+                    "Warns: 1",
+                ],
+            },
+        )
+
+        header = ["**Infractions**"]
+
+        self._method_subtests(self.cog.expanded_user_infraction_counts, test_values, header)
+
+    def test_user_nomination_counts_returns_correct_strings(self):
+        """The method should list the number of active and historical nominations for the user."""
+        test_values = (
+            {
+                "api response": [],
+                "expected_lines": ["This user has never been nominated."],
+            },
+            {
+                "api response": [{'active': True}],
+                "expected_lines": ["This user is **currently** nominated (1 nomination in total)."],
+            },
+            {
+                "api response": [{'active': True}, {'active': False}],
+                "expected_lines": ["This user is **currently** nominated (2 nominations in total)."],
+            },
+            {
+                "api response": [{'active': False}],
+                "expected_lines": ["This user has 1 historical nomination, but is currently not nominated."],
+            },
+            {
+                "api response": [{'active': False}, {'active': False}],
+                "expected_lines": ["This user has 2 historical nominations, but is currently not nominated."],
+            },
+
+        )
+
+        header = ["**Nominations**"]
+
+        self._method_subtests(self.cog.user_nomination_counts, test_values, header)
+
+
[email protected]("bot.cogs.information.time_since", new=unittest.mock.MagicMock(return_value="1 year ago"))
[email protected]("bot.cogs.information.constants.MODERATION_CHANNELS", new=[50])
+class UserEmbedTests(unittest.TestCase):
+    """Tests for the creation of the `!user` embed."""
+
+    def setUp(self):
+        """Common set-up steps done before for each test."""
+        self.bot = helpers.MockBot()
+        self.bot.api_client.get = helpers.AsyncMock()
+        self.cog = information.Information(self.bot)
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=helpers.AsyncMock(return_value=""))
+    def test_create_user_embed_uses_string_representation_of_user_in_title_if_nick_is_not_available(self):
+        """The embed should use the string representation of the user if they don't have a nick."""
+        ctx = helpers.MockContext(channel=helpers.MockTextChannel(id=1))
+        user = helpers.MockMember()
+        user.nick = None
+        user.__str__ = unittest.mock.Mock(return_value="Mr. Hemlock")
+
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        self.assertEqual(embed.title, "Mr. Hemlock")
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=helpers.AsyncMock(return_value=""))
+    def test_create_user_embed_uses_nick_in_title_if_available(self):
+        """The embed should use the nick if it's available."""
+        ctx = helpers.MockContext(channel=helpers.MockTextChannel(id=1))
+        user = helpers.MockMember()
+        user.nick = "Cat lover"
+        user.__str__ = unittest.mock.Mock(return_value="Mr. Hemlock")
+
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        self.assertEqual(embed.title, "Cat lover (Mr. Hemlock)")
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=helpers.AsyncMock(return_value=""))
+    def test_create_user_embed_ignores_everyone_role(self):
+        """Created `!user` embeds should not contain mention of the @everyone-role."""
+        ctx = helpers.MockContext(channel=helpers.MockTextChannel(id=1))
+        admins_role = helpers.MockRole(name='Admins')
+        admins_role.colour = 100
+
+        # A `MockMember` has the @Everyone role by default; we add the Admins to that.
+        user = helpers.MockMember(roles=[admins_role], top_role=admins_role)
+
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        self.assertIn("&Admins", embed.description)
+        self.assertNotIn("&Everyone", embed.description)
+
+    @unittest.mock.patch(f"{COG_PATH}.expanded_user_infraction_counts", new_callable=helpers.AsyncMock)
+    @unittest.mock.patch(f"{COG_PATH}.user_nomination_counts", new_callable=helpers.AsyncMock)
+    def test_create_user_embed_expanded_information_in_moderation_channels(self, nomination_counts, infraction_counts):
+        """The embed should contain expanded infractions and nomination info in mod channels."""
+        ctx = helpers.MockContext(channel=helpers.MockTextChannel(id=50))
+
+        moderators_role = helpers.MockRole(name='Moderators')
+        moderators_role.colour = 100
+
+        infraction_counts.return_value = "expanded infractions info"
+        nomination_counts.return_value = "nomination info"
+
+        user = helpers.MockMember(id=314, roles=[moderators_role], top_role=moderators_role)
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        infraction_counts.assert_called_once_with(user)
+        nomination_counts.assert_called_once_with(user)
+
+        self.assertEqual(
+            textwrap.dedent(f"""
+                **User Information**
+                Created: {"1 year ago"}
+                Profile: {user.mention}
+                ID: {user.id}
+
+                **Member Information**
+                Joined: {"1 year ago"}
+                Roles: &Moderators
+
+                expanded infractions info
+
+                nomination info
+            """).strip(),
+            embed.description
+        )
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new_callable=helpers.AsyncMock)
+    def test_create_user_embed_basic_information_outside_of_moderation_channels(self, infraction_counts):
+        """The embed should contain only basic infraction data outside of mod channels."""
+        ctx = helpers.MockContext(channel=helpers.MockTextChannel(id=100))
+
+        moderators_role = helpers.MockRole(name='Moderators')
+        moderators_role.colour = 100
+
+        infraction_counts.return_value = "basic infractions info"
+
+        user = helpers.MockMember(id=314, roles=[moderators_role], top_role=moderators_role)
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        infraction_counts.assert_called_once_with(user)
+
+        self.assertEqual(
+            textwrap.dedent(f"""
+                **User Information**
+                Created: {"1 year ago"}
+                Profile: {user.mention}
+                ID: {user.id}
+
+                **Member Information**
+                Joined: {"1 year ago"}
+                Roles: &Moderators
+
+                basic infractions info
+            """).strip(),
+            embed.description
+        )
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=helpers.AsyncMock(return_value=""))
+    def test_create_user_embed_uses_top_role_colour_when_user_has_roles(self):
+        """The embed should be created with the colour of the top role, if a top role is available."""
+        ctx = helpers.MockContext()
+
+        moderators_role = helpers.MockRole(name='Moderators')
+        moderators_role.colour = 100
+
+        user = helpers.MockMember(id=314, roles=[moderators_role], top_role=moderators_role)
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        self.assertEqual(embed.colour, discord.Colour(moderators_role.colour))
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=helpers.AsyncMock(return_value=""))
+    def test_create_user_embed_uses_blurple_colour_when_user_has_no_roles(self):
+        """The embed should be created with a blurple colour if the user has no assigned roles."""
+        ctx = helpers.MockContext()
+
+        user = helpers.MockMember(id=217)
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        self.assertEqual(embed.colour, discord.Colour.blurple())
+
+    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=helpers.AsyncMock(return_value=""))
+    def test_create_user_embed_uses_png_format_of_user_avatar_as_thumbnail(self):
+        """The embed thumbnail should be set to the user's avatar in `png` format."""
+        ctx = helpers.MockContext()
+
+        user = helpers.MockMember(id=217)
+        user.avatar_url_as.return_value = "avatar url"
+        embed = asyncio.run(self.cog.create_user_embed(ctx, user))
+
+        user.avatar_url_as.assert_called_once_with(format="png")
+        self.assertEqual(embed.thumbnail.url, "avatar url")
+
+
[email protected]("bot.cogs.information.constants")
+class UserCommandTests(unittest.TestCase):
+    """Tests for the `!user` command."""
+
+    def setUp(self):
+        """Set up steps executed before each test is run."""
+        self.bot = helpers.MockBot()
+        self.cog = information.Information(self.bot)
+
+        self.moderator_role = helpers.MockRole(name="Moderators", id=2, position=10)
+        self.flautist_role = helpers.MockRole(name="Flautists", id=3, position=2)
+        self.bassist_role = helpers.MockRole(name="Bassists", id=4, position=3)
+
+        self.author = helpers.MockMember(id=1, name="syntaxaire")
+        self.moderator = helpers.MockMember(id=2, name="riffautae", roles=[self.moderator_role])
+        self.target = helpers.MockMember(id=3, name="__fluzz__")
+
+    def test_regular_member_cannot_target_another_member(self, constants):
+        """A regular user should not be able to use `!user` targeting another user."""
+        constants.MODERATION_ROLES = [self.moderator_role.id]
+
+        ctx = helpers.MockContext(author=self.author)
+
+        asyncio.run(self.cog.user_info.callback(self.cog, ctx, self.target))
+
+        ctx.send.assert_called_once_with("You may not use this command on users other than yourself.")
+
+    def test_regular_member_cannot_use_command_outside_of_bot_commands(self, constants):
+        """A regular user should not be able to use this command outside of bot-commands."""
+        constants.MODERATION_ROLES = [self.moderator_role.id]
+        constants.STAFF_ROLES = [self.moderator_role.id]
+        constants.Channels.bot = 50
+
+        ctx = helpers.MockContext(author=self.author, channel=helpers.MockTextChannel(id=100))
+
+        msg = "Sorry, but you may only use this command within <#50>."
+        with self.assertRaises(InChannelCheckFailure, msg=msg):
+            asyncio.run(self.cog.user_info.callback(self.cog, ctx))
+
+    @unittest.mock.patch("bot.cogs.information.Information.create_user_embed", new_callable=helpers.AsyncMock)
+    def test_regular_user_may_use_command_in_bot_commands_channel(self, create_embed, constants):
+        """A regular user should be allowed to use `!user` targeting themselves in bot-commands."""
+        constants.STAFF_ROLES = [self.moderator_role.id]
+        constants.Channels.bot = 50
+
+        ctx = helpers.MockContext(author=self.author, channel=helpers.MockTextChannel(id=50))
+
+        asyncio.run(self.cog.user_info.callback(self.cog, ctx))
+
+        create_embed.assert_called_once_with(ctx, self.author)
+        ctx.send.assert_called_once()
+
+    @unittest.mock.patch("bot.cogs.information.Information.create_user_embed", new_callable=helpers.AsyncMock)
+    def test_regular_user_can_explicitly_target_themselves(self, create_embed, constants):
+        """A user should target itself with `!user` when a `user` argument was not provided."""
+        constants.STAFF_ROLES = [self.moderator_role.id]
+        constants.Channels.bot = 50
+
+        ctx = helpers.MockContext(author=self.author, channel=helpers.MockTextChannel(id=50))
+
+        asyncio.run(self.cog.user_info.callback(self.cog, ctx, self.author))
+
+        create_embed.assert_called_once_with(ctx, self.author)
+        ctx.send.assert_called_once()
+
+    @unittest.mock.patch("bot.cogs.information.Information.create_user_embed", new_callable=helpers.AsyncMock)
+    def test_staff_members_can_bypass_channel_restriction(self, create_embed, constants):
+        """Staff members should be able to bypass the bot-commands channel restriction."""
+        constants.STAFF_ROLES = [self.moderator_role.id]
+        constants.Channels.bot = 50
+
+        ctx = helpers.MockContext(author=self.moderator, channel=helpers.MockTextChannel(id=200))
+
+        asyncio.run(self.cog.user_info.callback(self.cog, ctx))
+
+        create_embed.assert_called_once_with(ctx, self.moderator)
+        ctx.send.assert_called_once()
+
+    @unittest.mock.patch("bot.cogs.information.Information.create_user_embed", new_callable=helpers.AsyncMock)
+    def test_moderators_can_target_another_member(self, create_embed, constants):
+        """A moderator should be able to use `!user` targeting another user."""
+        constants.MODERATION_ROLES = [self.moderator_role.id]
+        constants.STAFF_ROLES = [self.moderator_role.id]
+
+        ctx = helpers.MockContext(author=self.moderator, channel=helpers.MockTextChannel(id=50))
+
+        asyncio.run(self.cog.user_info.callback(self.cog, ctx, self.target))
+
+        create_embed.assert_called_once_with(ctx, self.target)
+        ctx.send.assert_called_once()
diff --git a/tests/bot/cogs/test_security.py b/tests/bot/cogs/test_security.py
new file mode 100644
index 000000000..9d1a62f7e
--- /dev/null
+++ b/tests/bot/cogs/test_security.py
@@ -0,0 +1,54 @@
+import unittest
+from unittest.mock import MagicMock
+
+from discord.ext.commands import NoPrivateMessage
+
+from bot.cogs import security
+from tests.helpers import MockBot, MockContext
+
+
+class SecurityCogTests(unittest.TestCase):
+    """Tests the `Security` cog."""
+
+    def setUp(self):
+        """Attach an instance of the cog to the class for tests."""
+        self.bot = MockBot()
+        self.cog = security.Security(self.bot)
+        self.ctx = MockContext()
+
+    def test_check_additions(self):
+        """The cog should add its checks after initialization."""
+        self.bot.check.assert_any_call(self.cog.check_on_guild)
+        self.bot.check.assert_any_call(self.cog.check_not_bot)
+
+    def test_check_not_bot_returns_false_for_humans(self):
+        """The bot check should return `True` when invoked with human authors."""
+        self.ctx.author.bot = False
+        self.assertTrue(self.cog.check_not_bot(self.ctx))
+
+    def test_check_not_bot_returns_true_for_robots(self):
+        """The bot check should return `False` when invoked with robotic authors."""
+        self.ctx.author.bot = True
+        self.assertFalse(self.cog.check_not_bot(self.ctx))
+
+    def test_check_on_guild_raises_when_outside_of_guild(self):
+        """When invoked outside of a guild, `check_on_guild` should cause an error."""
+        self.ctx.guild = None
+
+        with self.assertRaises(NoPrivateMessage, msg="This command cannot be used in private messages."):
+            self.cog.check_on_guild(self.ctx)
+
+    def test_check_on_guild_returns_true_inside_of_guild(self):
+        """When invoked inside of a guild, `check_on_guild` should return `True`."""
+        self.ctx.guild = "lemon's lemonade stand"
+        self.assertTrue(self.cog.check_on_guild(self.ctx))
+
+
+class SecurityCogLoadTests(unittest.TestCase):
+    """Tests loading the `Security` cog."""
+
+    def test_security_cog_load(self):
+        """Setup of the extension should call add_cog."""
+        bot = MagicMock()
+        security.setup(bot)
+        bot.add_cog.assert_called_once()
diff --git a/tests/bot/cogs/test_token_remover.py b/tests/bot/cogs/test_token_remover.py
new file mode 100644
index 000000000..a54b839d7
--- /dev/null
+++ b/tests/bot/cogs/test_token_remover.py
@@ -0,0 +1,131 @@
+import asyncio
+import logging
+import unittest
+from unittest.mock import MagicMock
+
+from discord import Colour
+
+from bot.cogs.token_remover import (
+    DELETION_MESSAGE_TEMPLATE,
+    TokenRemover,
+    setup as setup_cog,
+)
+from bot.constants import Channels, Colours, Event, Icons
+from tests.helpers import AsyncMock, MockBot, MockMessage
+
+
+class TokenRemoverTests(unittest.TestCase):
+    """Tests the `TokenRemover` cog."""
+
+    def setUp(self):
+        """Adds the cog, a bot, and a message to the instance for usage in tests."""
+        self.bot = MockBot()
+        self.bot.get_cog.return_value = MagicMock()
+        self.bot.get_cog.return_value.send_log_message = AsyncMock()
+        self.cog = TokenRemover(bot=self.bot)
+
+        self.msg = MockMessage(id=555, content='')
+        self.msg.author.__str__ = MagicMock()
+        self.msg.author.__str__.return_value = 'lemon'
+        self.msg.author.bot = False
+        self.msg.author.avatar_url_as.return_value = 'picture-lemon.png'
+        self.msg.author.id = 42
+        self.msg.author.mention = '@lemon'
+        self.msg.channel.mention = "#lemonade-stand"
+
+    def test_is_valid_user_id_is_true_for_numeric_content(self):
+        """A string decoding to numeric characters is a valid user ID."""
+        # MTIz = base64(123)
+        self.assertTrue(TokenRemover.is_valid_user_id('MTIz'))
+
+    def test_is_valid_user_id_is_false_for_alphabetic_content(self):
+        """A string decoding to alphabetic characters is not a valid user ID."""
+        # YWJj = base64(abc)
+        self.assertFalse(TokenRemover.is_valid_user_id('YWJj'))
+
+    def test_is_valid_timestamp_is_true_for_valid_timestamps(self):
+        """A string decoding to a valid timestamp should be recognized as such."""
+        self.assertTrue(TokenRemover.is_valid_timestamp('DN9r_A'))
+
+    def test_is_valid_timestamp_is_false_for_invalid_values(self):
+        """A string not decoding to a valid timestamp should not be recognized as such."""
+        # MTIz = base64(123)
+        self.assertFalse(TokenRemover.is_valid_timestamp('MTIz'))
+
+    def test_mod_log_property(self):
+        """The `mod_log` property should ask the bot to return the `ModLog` cog."""
+        self.bot.get_cog.return_value = 'lemon'
+        self.assertEqual(self.cog.mod_log, self.bot.get_cog.return_value)
+        self.bot.get_cog.assert_called_once_with('ModLog')
+
+    def test_ignores_bot_messages(self):
+        """When the message event handler is called with a bot message, nothing is done."""
+        self.msg.author.bot = True
+        coroutine = self.cog.on_message(self.msg)
+        self.assertIsNone(asyncio.run(coroutine))
+
+    def test_ignores_messages_without_tokens(self):
+        """Messages without anything looking like a token are ignored."""
+        for content in ('', 'lemon wins'):
+            with self.subTest(content=content):
+                self.msg.content = content
+                coroutine = self.cog.on_message(self.msg)
+                self.assertIsNone(asyncio.run(coroutine))
+
+    def test_ignores_messages_with_invalid_tokens(self):
+        """Messages with values that are invalid tokens are ignored."""
+        for content in ('foo.bar.baz', 'x.y.'):
+            with self.subTest(content=content):
+                self.msg.content = content
+                coroutine = self.cog.on_message(self.msg)
+                self.assertIsNone(asyncio.run(coroutine))
+
+    def test_censors_valid_tokens(self):
+        """Valid tokens are censored."""
+        cases = (
+            # (content, censored_token)
+            ('MTIz.DN9R_A.xyz', 'MTIz.DN9R_A.xxx'),
+        )
+
+        for content, censored_token in cases:
+            with self.subTest(content=content, censored_token=censored_token):
+                self.msg.content = content
+                coroutine = self.cog.on_message(self.msg)
+                with self.assertLogs(logger='bot.cogs.token_remover', level=logging.DEBUG) as cm:
+                    self.assertIsNone(asyncio.run(coroutine))  # no return value
+
+                [line] = cm.output
+                log_message = (
+                    "Censored a seemingly valid token sent by "
+                    "lemon (`42`) in #lemonade-stand, "
+                    f"token was `{censored_token}`"
+                )
+                self.assertIn(log_message, line)
+
+                self.msg.delete.assert_called_once_with()
+                self.msg.channel.send.assert_called_once_with(
+                    DELETION_MESSAGE_TEMPLATE.format(mention='@lemon')
+                )
+                self.bot.get_cog.assert_called_with('ModLog')
+                self.msg.author.avatar_url_as.assert_called_once_with(static_format='png')
+
+                mod_log = self.bot.get_cog.return_value
+                mod_log.ignore.assert_called_once_with(Event.message_delete, self.msg.id)
+                mod_log.send_log_message.assert_called_once_with(
+                    icon_url=Icons.token_removed,
+                    colour=Colour(Colours.soft_red),
+                    title="Token removed!",
+                    text=log_message,
+                    thumbnail='picture-lemon.png',
+                    channel_id=Channels.mod_alerts
+                )
+
+
+class TokenRemoverSetupTests(unittest.TestCase):
+    """Tests setup of the `TokenRemover` cog."""
+
+    def test_setup(self):
+        """Setup of the extension should call add_cog."""
+        bot = MockBot()
+        setup_cog(bot)
+        bot.add_cog.assert_called_once()
diff --git a/tests/utils/__init__.py b/tests/bot/patches/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/utils/__init__.py
+++ b/tests/bot/patches/__init__.py
diff --git a/tests/bot/resources/__init__.py b/tests/bot/resources/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/resources/__init__.py
diff --git a/tests/bot/resources/test_resources.py b/tests/bot/resources/test_resources.py
new file mode 100644
index 000000000..73937cfa6
--- /dev/null
+++ b/tests/bot/resources/test_resources.py
@@ -0,0 +1,17 @@
+import json
+import unittest
+from pathlib import Path
+
+
+class ResourceValidationTests(unittest.TestCase):
+    """Validates resources used by the bot."""
+    def test_stars_valid(self):
+        """The resource `bot/resources/stars.json` should contain a list of strings."""
+        path = Path('bot', 'resources', 'stars.json')
+        content = path.read_text()
+        data = json.loads(content)
+
+        self.assertIsInstance(data, list)
+        for name in data:
+            with self.subTest(name=name):
+                self.assertIsInstance(name, str)
diff --git a/tests/bot/rules/__init__.py b/tests/bot/rules/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/rules/__init__.py
diff --git a/tests/bot/rules/test_attachments.py b/tests/bot/rules/test_attachments.py
new file mode 100644
index 000000000..d7187f315
--- /dev/null
+++ b/tests/bot/rules/test_attachments.py
@@ -0,0 +1,98 @@
+import unittest
+from typing import List, NamedTuple, Tuple
+
+from bot.rules import attachments
+from tests.helpers import MockMessage, async_test
+
+
+class Case(NamedTuple):
+    recent_messages: List[MockMessage]
+    culprit: Tuple[str]
+    total_attachments: int
+
+
+def msg(author: str, total_attachments: int) -> MockMessage:
+    """Builds a message with `total_attachments` attachments."""
+    return MockMessage(author=author, attachments=list(range(total_attachments)))
+
+
+class AttachmentRuleTests(unittest.TestCase):
+    """Tests applying the `attachments` antispam rule."""
+
+    def setUp(self):
+        self.config = {"max": 5}
+
+    @async_test
+    async def test_allows_messages_without_too_many_attachments(self):
+        """Messages without too many attachments are allowed as-is."""
+        cases = (
+            [msg("bob", 0), msg("bob", 0), msg("bob", 0)],
+            [msg("bob", 2), msg("bob", 2)],
+            [msg("bob", 2), msg("alice", 2), msg("bob", 2)],
+        )
+
+        for recent_messages in cases:
+            last_message = recent_messages[0]
+
+            with self.subTest(
+                last_message=last_message,
+                recent_messages=recent_messages,
+                config=self.config
+            ):
+                self.assertIsNone(
+                    await attachments.apply(last_message, recent_messages, self.config)
+                )
+
+    @async_test
+    async def test_disallows_messages_with_too_many_attachments(self):
+        """Messages with too many attachments trigger the rule."""
+        cases = (
+            Case(
+                [msg("bob", 4), msg("bob", 0), msg("bob", 6)],
+                ("bob",),
+                10
+            ),
+            Case(
+                [msg("bob", 4), msg("alice", 6), msg("bob", 2)],
+                ("bob",),
+                6
+            ),
+            Case(
+                [msg("alice", 6)],
+                ("alice",),
+                6
+            ),
+            (
+                [msg("alice", 1) for _ in range(6)],
+                ("alice",),
+                6
+            ),
+        )
+
+        for recent_messages, culprit, total_attachments in cases:
+            last_message = recent_messages[0]
+            relevant_messages = tuple(
+                msg
+                for msg in recent_messages
+                if (
+                    msg.author == last_message.author
+                    and len(msg.attachments) > 0
+                )
+            )
+
+            with self.subTest(
+                last_message=last_message,
+                recent_messages=recent_messages,
+                relevant_messages=relevant_messages,
+                total_attachments=total_attachments,
+                config=self.config
+            ):
+                desired_output = (
+                    f"sent {total_attachments} attachments in {self.config['max']}s",
+                    culprit,
+                    relevant_messages
+                )
+                self.assertTupleEqual(
+                    await attachments.apply(last_message, recent_messages, self.config),
+                    desired_output
+                )
diff --git a/tests/bot/rules/test_links.py b/tests/bot/rules/test_links.py
new file mode 100644
index 000000000..02a5d5501
--- /dev/null
+++ b/tests/bot/rules/test_links.py
@@ -0,0 +1,97 @@
+import unittest
+from typing import List, NamedTuple, Tuple
+
+from bot.rules import links
+from tests.helpers import MockMessage, async_test
+
+
+class Case(NamedTuple):
+    recent_messages: List[MockMessage]
+    culprit: Tuple[str]
+    total_links: int
+
+
+def msg(author: str, total_links: int) -> MockMessage:
+    """Makes a message with `total_links` links."""
+    content = " ".join(["https://pydis.com"] * total_links)
+    return MockMessage(author=author, content=content)
+
+
+class LinksTests(unittest.TestCase):
+    """Tests applying the `links` rule."""
+
+    def setUp(self):
+        self.config = {
+            "max": 2,
+            "interval": 10
+        }
+
+    @async_test
+    async def test_links_within_limit(self):
+        """Messages with an allowed amount of links."""
+        cases = (
+            [msg("bob", 0)],
+            [msg("bob", 2)],
+            [msg("bob", 3)],  # Filter only applies if len(messages_with_links) > 1
+            [msg("bob", 1), msg("bob", 1)],
+            [msg("bob", 2), msg("alice", 2)]  # Only messages from latest author count
+        )
+
+        for recent_messages in cases:
+            last_message = recent_messages[0]
+
+            with self.subTest(
+                last_message=last_message,
+                recent_messages=recent_messages,
+                config=self.config
+            ):
+                self.assertIsNone(
+                    await links.apply(last_message, recent_messages, self.config)
+                )
+
+    @async_test
+    async def test_links_exceeding_limit(self):
+        """Messages with a a higher than allowed amount of links."""
+        cases = (
+            Case(
+                [msg("bob", 1), msg("bob", 2)],
+                ("bob",),
+                3
+            ),
+            Case(
+                [msg("alice", 1), msg("alice", 1), msg("alice", 1)],
+                ("alice",),
+                3
+            ),
+            Case(
+                [msg("alice", 2), msg("bob", 3), msg("alice", 1)],
+                ("alice",),
+                3
+            )
+        )
+
+        for recent_messages, culprit, total_links in cases:
+            last_message = recent_messages[0]
+            relevant_messages = tuple(
+                msg
+                for msg in recent_messages
+                if msg.author == last_message.author
+            )
+
+            with self.subTest(
+                last_message=last_message,
+                recent_messages=recent_messages,
+                relevant_messages=relevant_messages,
+                culprit=culprit,
+                total_links=total_links,
+                config=self.config
+            ):
+                desired_output = (
+                    f"sent {total_links} links in {self.config['interval']}s",
+                    culprit,
+                    relevant_messages
+                )
+                self.assertTupleEqual(
+                    await links.apply(last_message, recent_messages, self.config),
+                    desired_output
+                )
diff --git a/tests/bot/rules/test_mentions.py b/tests/bot/rules/test_mentions.py
new file mode 100644
index 000000000..ad49ead32
--- /dev/null
+++ b/tests/bot/rules/test_mentions.py
@@ -0,0 +1,95 @@
+import unittest
+from typing import List, NamedTuple, Tuple
+
+from bot.rules import mentions
+from tests.helpers import MockMessage, async_test
+
+
+class Case(NamedTuple):
+    recent_messages: List[MockMessage]
+    culprit: Tuple[str]
+    total_mentions: int
+
+
+def msg(author: str, total_mentions: int) -> MockMessage:
+    """Makes a message with `total_mentions` mentions."""
+    return MockMessage(author=author, mentions=list(range(total_mentions)))
+
+
+class TestMentions(unittest.TestCase):
+    """Tests applying the `mentions` antispam rule."""
+
+    def setUp(self):
+        self.config = {
+            "max": 2,
+            "interval": 10
+        }
+
+    @async_test
+    async def test_mentions_within_limit(self):
+        """Messages with an allowed amount of mentions."""
+        cases = (
+            [msg("bob", 0)],
+            [msg("bob", 2)],
+            [msg("bob", 1), msg("bob", 1)],
+            [msg("bob", 1), msg("alice", 2)]
+        )
+
+        for recent_messages in cases:
+            last_message = recent_messages[0]
+
+            with self.subTest(
+                last_message=last_message,
+                recent_messages=recent_messages,
+                config=self.config
+            ):
+                self.assertIsNone(
+                    await mentions.apply(last_message, recent_messages, self.config)
+                )
+
+    @async_test
+    async def test_mentions_exceeding_limit(self):
+        """Messages with a higher than allowed amount of mentions."""
+        cases = (
+            Case(
+                [msg("bob", 3)],
+                ("bob",),
+                3
+            ),
+            Case(
+                [msg("alice", 2), msg("alice", 0), msg("alice", 1)],
+                ("alice",),
+                3
+            ),
+            Case(
+                [msg("bob", 2), msg("alice", 3), msg("bob", 2)],
+                ("bob",),
+                4
+            )
+        )
+
+        for recent_messages, culprit, total_mentions in cases:
+            last_message = recent_messages[0]
+            relevant_messages = tuple(
+                msg
+                for msg in recent_messages
+                if msg.author == last_message.author
+            )
+
+            with self.subTest(
+                last_message=last_message,
+                recent_messages=recent_messages,
+                relevant_messages=relevant_messages,
+                culprit=culprit,
+                total_mentions=total_mentions,
+                cofig=self.config
+            ):
+                desired_output = (
+                    f"sent {total_mentions} mentions in {self.config['interval']}s",
+                    culprit,
+                    relevant_messages
+                )
+                self.assertTupleEqual(
+                    await mentions.apply(last_message, recent_messages, self.config),
+                    desired_output
+                )
diff --git a/tests/bot/test_api.py b/tests/bot/test_api.py
new file mode 100644
index 000000000..5a88adc5c
--- /dev/null
+++ b/tests/bot/test_api.py
@@ -0,0 +1,136 @@
+import logging
+import unittest
+from unittest.mock import MagicMock, patch
+
+from bot import api
+from tests.base import LoggingTestCase
+from tests.helpers import async_test
+
+
+class APIClientTests(unittest.TestCase):
+    """Tests for the bot's API client."""
+
+    @classmethod
+    def setUpClass(cls):
+        """Sets up the shared fixtures for the tests."""
+        cls.error_api_response = MagicMock()
+        cls.error_api_response.status = 999
+
+    def test_loop_is_not_running_by_default(self):
+        """The event loop should not be running by default."""
+        self.assertFalse(api.loop_is_running())
+
+    @async_test
+    async def test_loop_is_running_in_async_context(self):
+        """The event loop should be running in an async context."""
+        self.assertTrue(api.loop_is_running())
+
+    def test_response_code_error_default_initialization(self):
+        """Test the default initialization of `ResponseCodeError` without `text` or `json`"""
+        error = api.ResponseCodeError(response=self.error_api_response)
+
+        self.assertIs(error.status, self.error_api_response.status)
+        self.assertEqual(error.response_json, {})
+        self.assertEqual(error.response_text, "")
+        self.assertIs(error.response, self.error_api_response)
+
+    def test_responde_code_error_string_representation_default_initialization(self):
+        """Test the string representation of `ResponseCodeError` initialized without text or json."""
+        error = api.ResponseCodeError(response=self.error_api_response)
+        self.assertEqual(str(error), f"Status: {self.error_api_response.status} Response: ")
+
+    def test_response_code_error_initialization_with_json(self):
+        """Test the initialization of `ResponseCodeError` with json."""
+        json_data = {'hello': 'world'}
+        error = api.ResponseCodeError(
+            response=self.error_api_response,
+            response_json=json_data,
+        )
+        self.assertEqual(error.response_json, json_data)
+        self.assertEqual(error.response_text, "")
+
+    def test_response_code_error_string_representation_with_nonempty_response_json(self):
+        """Test the string representation of `ResponseCodeError` initialized with json."""
+        json_data = {'hello': 'world'}
+        error = api.ResponseCodeError(
+            response=self.error_api_response,
+            response_json=json_data
+        )
+        self.assertEqual(str(error), f"Status: {self.error_api_response.status} Response: {json_data}")
+
+    def test_response_code_error_initialization_with_text(self):
+        """Test the initialization of `ResponseCodeError` with text."""
+        text_data = 'Lemon will eat your soul'
+        error = api.ResponseCodeError(
+            response=self.error_api_response,
+            response_text=text_data,
+        )
+        self.assertEqual(error.response_text, text_data)
+        self.assertEqual(error.response_json, {})
+
+    def test_response_code_error_string_representation_with_nonempty_response_text(self):
+        """Test the string representation of `ResponseCodeError` initialized with text."""
+        text_data = 'Lemon will eat your soul'
+        error = api.ResponseCodeError(
+            response=self.error_api_response,
+            response_text=text_data
+        )
+        self.assertEqual(str(error), f"Status: {self.error_api_response.status} Response: {text_data}")
+
+
+class LoggingHandlerTests(LoggingTestCase):
+    """Tests the bot's API Log Handler."""
+
+    @classmethod
+    def setUpClass(cls):
+        cls.debug_log_record = logging.LogRecord(
+            name='my.logger', level=logging.DEBUG,
+            pathname='my/logger.py', lineno=666,
+            msg="Lemon wins", args=(),
+            exc_info=None
+        )
+
+        cls.trace_log_record = logging.LogRecord(
+            name='my.logger', level=logging.TRACE,
+            pathname='my/logger.py', lineno=666,
+            msg="This will not be logged", args=(),
+            exc_info=None
+        )
+
+    def setUp(self):
+        self.log_handler = api.APILoggingHandler(None)
+
+    def test_emit_appends_to_queue_with_stopped_event_loop(self):
+        """Test if `APILoggingHandler.emit` appends to queue when the event loop is not running."""
+        with patch("bot.api.APILoggingHandler.ship_off") as ship_off:
+            # Patch `ship_off` to ease testing against the return value of this coroutine.
+            ship_off.return_value = 42
+            self.log_handler.emit(self.debug_log_record)
+
+        self.assertListEqual(self.log_handler.queue, [42])
+
+    def test_emit_ignores_less_than_debug(self):
+        """`APILoggingHandler.emit` should not queue logs with a log level lower than DEBUG."""
+        self.log_handler.emit(self.trace_log_record)
+        self.assertListEqual(self.log_handler.queue, [])
+
+    def test_schedule_queued_tasks_for_empty_queue(self):
+        """`APILoggingHandler` should not schedule anything when the queue is empty."""
+        with self.assertNotLogs(level=logging.DEBUG):
+            self.log_handler.schedule_queued_tasks()
+
+    def test_schedule_queued_tasks_for_nonempty_queue(self):
+        """`APILoggingHandler` should schedule logs when the queue is not empty."""
+        log = logging.getLogger("bot.api")
+
+        with self.assertLogs(logger=log, level=logging.DEBUG) as logs, patch('asyncio.create_task') as create_task:
+            self.log_handler.queue = [555]
+            self.log_handler.schedule_queued_tasks()
+            self.assertListEqual(self.log_handler.queue, [])
+            create_task.assert_called_once_with(555)
+
+            [record] = logs.records
+            self.assertEqual(record.message, "Scheduled 1 pending logging tasks.")
+            self.assertEqual(record.levelno, logging.DEBUG)
+            self.assertEqual(record.name, 'bot.api')
+            self.assertIn('via_handler', record.__dict__)
diff --git a/tests/bot/test_constants.py b/tests/bot/test_constants.py
new file mode 100644
index 000000000..dae7c066c
--- /dev/null
+++ b/tests/bot/test_constants.py
@@ -0,0 +1,26 @@
+import inspect
+import unittest
+
+from bot import constants
+
+
+class ConstantsTests(unittest.TestCase):
+    """Tests for our constants."""
+
+    def test_section_configuration_matches_type_specification(self):
+        """The section annotations should match the actual types of the sections."""
+
+        sections = (
+            cls
+            for (name, cls) in inspect.getmembers(constants)
+            if hasattr(cls, 'section') and isinstance(cls, type)
+        )
+        for section in sections:
+            for name, annotation in section.__annotations__.items():
+                with self.subTest(section=section, name=name, annotation=annotation):
+                    value = getattr(section, name)
+
+                    if getattr(annotation, '_name', None) in ('Dict', 'List'):
+                        self.skipTest("Cannot validate containers yet.")
+
+                    self.assertIsInstance(value, annotation)
diff --git a/tests/bot/test_converters.py b/tests/bot/test_converters.py
new file mode 100644
index 000000000..b2b78d9dd
--- /dev/null
+++ b/tests/bot/test_converters.py
@@ -0,0 +1,273 @@
+import asyncio
+import datetime
+import unittest
+from unittest.mock import MagicMock, patch
+
+from dateutil.relativedelta import relativedelta
+from discord.ext.commands import BadArgument
+
+from bot.converters import (
+    Duration,
+    ISODateTime,
+    TagContentConverter,
+    TagNameConverter,
+    ValidPythonIdentifier,
+)
+
+
+class ConverterTests(unittest.TestCase):
+    """Tests our custom argument converters."""
+
+    @classmethod
+    def setUpClass(cls):
+        cls.context = MagicMock
+        cls.context.author = 'bob'
+
+        cls.fixed_utc_now = datetime.datetime.fromisoformat('2019-01-01T00:00:00')
+
+    def test_tag_content_converter_for_valid(self):
+        """TagContentConverter should return correct values for valid input."""
+        test_values = (
+            ('hello', 'hello'),
+            ('  h ello  ', 'h ello'),
+        )
+
+        for content, expected_conversion in test_values:
+            with self.subTest(content=content, expected_conversion=expected_conversion):
+                conversion = asyncio.run(TagContentConverter.convert(self.context, content))
+                self.assertEqual(conversion, expected_conversion)
+
+    def test_tag_content_converter_for_invalid(self):
+        """TagContentConverter should raise the proper exception for invalid input."""
+        test_values = (
+            ('', "Tag contents should not be empty, or filled with whitespace."),
+            ('   ', "Tag contents should not be empty, or filled with whitespace."),
+        )
+
+        for value, exception_message in test_values:
+            with self.subTest(tag_content=value, exception_message=exception_message):
+                with self.assertRaises(BadArgument, msg=exception_message):
+                    asyncio.run(TagContentConverter.convert(self.context, value))
+
+    def test_tag_name_converter_for_valid(self):
+        """TagNameConverter should return the correct values for valid tag names."""
+        test_values = (
+            ('tracebacks', 'tracebacks'),
+            ('Tracebacks', 'tracebacks'),
+            ('  Tracebacks  ', 'tracebacks'),
+        )
+
+        for name, expected_conversion in test_values:
+            with self.subTest(name=name, expected_conversion=expected_conversion):
+                conversion = asyncio.run(TagNameConverter.convert(self.context, name))
+                self.assertEqual(conversion, expected_conversion)
+
+    def test_tag_name_converter_for_invalid(self):
+        """TagNameConverter should raise the correct exception for invalid tag names."""
+        test_values = (
+            ('👋', "Don't be ridiculous, you can't use that character!"),
+            ('', "Tag names should not be empty, or filled with whitespace."),
+            ('  ', "Tag names should not be empty, or filled with whitespace."),
+            ('42', "Tag names can't be numbers."),
+            ('x' * 128, "Are you insane? That's way too long!"),
+        )
+
+        for invalid_name, exception_message in test_values:
+            with self.subTest(invalid_name=invalid_name, exception_message=exception_message):
+                with self.assertRaises(BadArgument, msg=exception_message):
+                    asyncio.run(TagNameConverter.convert(self.context, invalid_name))
+
+    def test_valid_python_identifier_for_valid(self):
+        """ValidPythonIdentifier returns valid identifiers unchanged."""
+        test_values = ('foo', 'lemon')
+
+        for name in test_values:
+            with self.subTest(identifier=name):
+                conversion = asyncio.run(ValidPythonIdentifier.convert(self.context, name))
+                self.assertEqual(name, conversion)
+
+    def test_valid_python_identifier_for_invalid(self):
+        """ValidPythonIdentifier raises the proper exception for invalid identifiers."""
+        test_values = ('nested.stuff', '#####')
+
+        for name in test_values:
+            with self.subTest(identifier=name):
+                exception_message = f'`{name}` is not a valid Python identifier'
+                with self.assertRaises(BadArgument, msg=exception_message):
+                    asyncio.run(ValidPythonIdentifier.convert(self.context, name))
+
+    def test_duration_converter_for_valid(self):
+        """Duration returns the correct `datetime` for valid duration strings."""
+        test_values = (
+            # Simple duration strings
+            ('1Y', {"years": 1}),
+            ('1y', {"years": 1}),
+            ('1year', {"years": 1}),
+            ('1years', {"years": 1}),
+            ('1m', {"months": 1}),
+            ('1month', {"months": 1}),
+            ('1months', {"months": 1}),
+            ('1w', {"weeks": 1}),
+            ('1W', {"weeks": 1}),
+            ('1week', {"weeks": 1}),
+            ('1weeks', {"weeks": 1}),
+            ('1d', {"days": 1}),
+            ('1D', {"days": 1}),
+            ('1day', {"days": 1}),
+            ('1days', {"days": 1}),
+            ('1h', {"hours": 1}),
+            ('1H', {"hours": 1}),
+            ('1hour', {"hours": 1}),
+            ('1hours', {"hours": 1}),
+            ('1M', {"minutes": 1}),
+            ('1minute', {"minutes": 1}),
+            ('1minutes', {"minutes": 1}),
+            ('1s', {"seconds": 1}),
+            ('1S', {"seconds": 1}),
+            ('1second', {"seconds": 1}),
+            ('1seconds', {"seconds": 1}),
+
+            # Complex duration strings
+            (
+                '1y1m1w1d1H1M1S',
+                {
+                    "years": 1,
+                    "months": 1,
+                    "weeks": 1,
+                    "days": 1,
+                    "hours": 1,
+                    "minutes": 1,
+                    "seconds": 1
+                }
+            ),
+            ('5y100S', {"years": 5, "seconds": 100}),
+            ('2w28H', {"weeks": 2, "hours": 28}),
+
+            # Duration strings with spaces
+            ('1 year 2 months', {"years": 1, "months": 2}),
+            ('1d 2H', {"days": 1, "hours": 2}),
+            ('1 week2 days', {"weeks": 1, "days": 2}),
+        )
+
+        converter = Duration()
+
+        for duration, duration_dict in test_values:
+            expected_datetime = self.fixed_utc_now + relativedelta(**duration_dict)
+
+            with patch('bot.converters.datetime') as mock_datetime:
+                mock_datetime.utcnow.return_value = self.fixed_utc_now
+
+                with self.subTest(duration=duration, duration_dict=duration_dict):
+                    converted_datetime = asyncio.run(converter.convert(self.context, duration))
+                    self.assertEqual(converted_datetime, expected_datetime)
+
+    def test_duration_converter_for_invalid(self):
+        """Duration raises the right exception for invalid duration strings."""
+        test_values = (
+            # Units in wrong order
+            ('1d1w'),
+            ('1s1y'),
+
+            # Duplicated units
+            ('1 year 2 years'),
+            ('1 M 10 minutes'),
+
+            # Unknown substrings
+            ('1MVes'),
+            ('1y3breads'),
+
+            # Missing amount
+            ('ym'),
+
+            # Incorrect whitespace
+            (" 1y"),
+            ("1S "),
+            ("1y  1m"),
+
+            # Garbage
+            ('Guido van Rossum'),
+            ('lemon lemon lemon lemon lemon lemon lemon'),
+        )
+
+        converter = Duration()
+
+        for invalid_duration in test_values:
+            with self.subTest(invalid_duration=invalid_duration):
+                exception_message = f'`{invalid_duration}` is not a valid duration string.'
+                with self.assertRaises(BadArgument, msg=exception_message):
+                    asyncio.run(converter.convert(self.context, invalid_duration))
+
+    def test_isodatetime_converter_for_valid(self):
+        """ISODateTime converter returns correct datetime for valid datetime string."""
+        test_values = (
+            # `YYYY-mm-ddTHH:MM:SSZ` | `YYYY-mm-dd HH:MM:SSZ`
+            ('2019-09-02T02:03:05Z', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02 02:03:05Z', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+
+            # `YYYY-mm-ddTHH:MM:SS±HH:MM` | `YYYY-mm-dd HH:MM:SS±HH:MM`
+            ('2019-09-02T03:18:05+01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02 03:18:05+01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02T00:48:05-01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02 00:48:05-01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+
+            # `YYYY-mm-ddTHH:MM:SS±HHMM` | `YYYY-mm-dd HH:MM:SS±HHMM`
+            ('2019-09-02T03:18:05+0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02 03:18:05+0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02T00:48:05-0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02 00:48:05-0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+
+            # `YYYY-mm-ddTHH:MM:SS±HH` | `YYYY-mm-dd HH:MM:SS±HH`
+            ('2019-09-02 03:03:05+01', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02T01:03:05-01', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+
+            # `YYYY-mm-ddTHH:MM:SS` | `YYYY-mm-dd HH:MM:SS`
+            ('2019-09-02T02:03:05', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+            ('2019-09-02 02:03:05', datetime.datetime(2019, 9, 2, 2, 3, 5)),
+
+            # `YYYY-mm-ddTHH:MM` | `YYYY-mm-dd HH:MM`
+            ('2019-11-12T09:15', datetime.datetime(2019, 11, 12, 9, 15)),
+            ('2019-11-12 09:15', datetime.datetime(2019, 11, 12, 9, 15)),
+
+            # `YYYY-mm-dd`
+            ('2019-04-01', datetime.datetime(2019, 4, 1)),
+
+            # `YYYY-mm`
+            ('2019-02-01', datetime.datetime(2019, 2, 1)),
+
+            # `YYYY`
+            ('2025', datetime.datetime(2025, 1, 1)),
+        )
+
+        converter = ISODateTime()
+
+        for datetime_string, expected_dt in test_values:
+            with self.subTest(datetime_string=datetime_string, expected_dt=expected_dt):
+                converted_dt = asyncio.run(converter.convert(self.context, datetime_string))
+                self.assertIsNone(converted_dt.tzinfo)
+                self.assertEqual(converted_dt, expected_dt)
+
+    def test_isodatetime_converter_for_invalid(self):
+        """ISODateTime converter raises the correct exception for invalid datetime strings."""
+        test_values = (
+            # Make sure it doesn't interfere with the Duration converter
+            ('1Y'),
+            ('1d'),
+            ('1H'),
+
+            # Check if it fails when only providing the optional time part
+            ('10:10:10'),
+            ('10:00'),
+
+            # Invalid date format
+            ('19-01-01'),
+
+            # Other non-valid strings
+            ('fisk the tag master'),
+        )
+
+        converter = ISODateTime()
+        for datetime_string in test_values:
+            with self.subTest(datetime_string=datetime_string):
+                exception_message = f"`{datetime_string}` is not a valid ISO-8601 datetime string"
+                with self.assertRaises(BadArgument, msg=exception_message):
+                    asyncio.run(converter.convert(self.context, datetime_string))
diff --git a/tests/test_pagination.py b/tests/bot/test_pagination.py
index 11d6541ae..0a734b505 100644
--- a/tests/test_pagination.py
+++ b/tests/bot/test_pagination.py
@@ -1,28 +1,35 @@
 from unittest import TestCase
 
-import pytest
-
 from bot import pagination
 
 
 class LinePaginatorTests(TestCase):
+    """Tests functionality of the `LinePaginator`."""
+
     def setUp(self):
+        """Create a paginator for the test method."""
         self.paginator = pagination.LinePaginator(prefix='', suffix='', max_size=30)
 
     def test_add_line_raises_on_too_long_lines(self):
+        """`add_line` should raise a `RuntimeError` for too long lines."""
         message = f"Line exceeds maximum page size {self.paginator.max_size - 2}"
-        with pytest.raises(RuntimeError, match=message):
+        with self.assertRaises(RuntimeError, msg=message):
             self.paginator.add_line('x' * self.paginator.max_size)
 
     def test_add_line_works_on_small_lines(self):
+        """`add_line` should allow small lines to be added."""
         self.paginator.add_line('x' * (self.paginator.max_size - 3))
 
 
 class ImagePaginatorTests(TestCase):
+    """Tests functionality of the `ImagePaginator`."""
+
     def setUp(self):
+        """Create a paginator for the test method."""
         self.paginator = pagination.ImagePaginator()
 
     def test_add_image_appends_image(self):
+        """`add_image` appends the image to the image list."""
         image = 'lemon'
         self.paginator.add_image(image)
 
diff --git a/tests/bot/test_utils.py b/tests/bot/test_utils.py
new file mode 100644
index 000000000..58ae2a81a
--- /dev/null
+++ b/tests/bot/test_utils.py
@@ -0,0 +1,52 @@
+import unittest
+
+from bot import utils
+
+
+class CaseInsensitiveDictTests(unittest.TestCase):
+    """Tests for the `CaseInsensitiveDict` container."""
+
+    def test_case_insensitive_key_access(self):
+        """Tests case insensitive key access and storage."""
+        instance = utils.CaseInsensitiveDict()
+
+        key = 'LEMON'
+        value = 'trees'
+
+        instance[key] = value
+        self.assertIn(key, instance)
+        self.assertEqual(instance.get(key), value)
+        self.assertEqual(instance.get(key.casefold()), value)
+        self.assertEqual(instance.pop(key.casefold()), value)
+        self.assertNotIn(key, instance)
+        self.assertNotIn(key.casefold(), instance)
+
+        instance.setdefault(key, value)
+        del instance[key]
+        self.assertNotIn(key, instance)
+
+    def test_initialization_from_kwargs(self):
+        """Tests creating the dictionary from keyword arguments."""
+        instance = utils.CaseInsensitiveDict({'FOO': 'bar'})
+        self.assertEqual(instance['foo'], 'bar')
+
+    def test_update_from_other_mapping(self):
+        """Tests updating the dictionary from another mapping."""
+        instance = utils.CaseInsensitiveDict()
+        instance.update({'FOO': 'bar'})
+        self.assertEqual(instance['foo'], 'bar')
+
+
+class ChunkTests(unittest.TestCase):
+    """Tests the `chunk` method."""
+
+    def test_empty_chunking(self):
+        """Tests chunking on an empty iterable."""
+        generator = utils.chunks(iterable=[], size=5)
+        self.assertEqual(list(generator), [])
+
+    def test_list_chunking(self):
+        """Tests chunking a non-empty list."""
+        iterable = [1, 2, 3, 4, 5]
+        generator = utils.chunks(iterable=iterable, size=2)
+        self.assertEqual(list(generator), [[1, 2], [3, 4], [5]])
diff --git a/tests/bot/utils/__init__.py b/tests/bot/utils/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/utils/__init__.py
diff --git a/tests/bot/utils/test_checks.py b/tests/bot/utils/test_checks.py
new file mode 100644
index 000000000..9610771e5
--- /dev/null
+++ b/tests/bot/utils/test_checks.py
@@ -0,0 +1,51 @@
+import unittest
+
+from bot.utils import checks
+from tests.helpers import MockContext, MockRole
+
+
+class ChecksTests(unittest.TestCase):
+    """Tests the check functions defined in `bot.checks`."""
+
+    def setUp(self):
+        self.ctx = MockContext()
+
+    def test_with_role_check_without_guild(self):
+        """`with_role_check` returns `False` if `Context.guild` is None."""
+        self.ctx.guild = None
+        self.assertFalse(checks.with_role_check(self.ctx))
+
+    def test_with_role_check_without_required_roles(self):
+        """`with_role_check` returns `False` if `Context.author` lacks the required role."""
+        self.ctx.author.roles = []
+        self.assertFalse(checks.with_role_check(self.ctx))
+
+    def test_with_role_check_with_guild_and_required_role(self):
+        """`with_role_check` returns `True` if `Context.author` has the required role."""
+        self.ctx.author.roles.append(MockRole(id=10))
+        self.assertTrue(checks.with_role_check(self.ctx, 10))
+
+    def test_without_role_check_without_guild(self):
+        """`without_role_check` should return `False` when `Context.guild` is None."""
+        self.ctx.guild = None
+        self.assertFalse(checks.without_role_check(self.ctx))
+
+    def test_without_role_check_returns_false_with_unwanted_role(self):
+        """`without_role_check` returns `False` if `Context.author` has unwanted role."""
+        role_id = 42
+        self.ctx.author.roles.append(MockRole(id=role_id))
+        self.assertFalse(checks.without_role_check(self.ctx, role_id))
+
+    def test_without_role_check_returns_true_without_unwanted_role(self):
+        """`without_role_check` returns `True` if `Context.author` does not have unwanted role."""
+        role_id = 42
+        self.ctx.author.roles.append(MockRole(id=role_id))
+        self.assertTrue(checks.without_role_check(self.ctx, role_id + 10))
+
+    def test_in_channel_check_for_correct_channel(self):
+        self.ctx.channel.id = 42
+        self.assertTrue(checks.in_channel_check(self.ctx, *[42]))
+
+    def test_in_channel_check_for_incorrect_channel(self):
+        self.ctx.channel.id = 42 + 10
+        self.assertFalse(checks.in_channel_check(self.ctx, *[42]))
diff --git a/tests/bot/utils/test_time.py b/tests/bot/utils/test_time.py
new file mode 100644
index 000000000..69f35f2f5
--- /dev/null
+++ b/tests/bot/utils/test_time.py
@@ -0,0 +1,162 @@
+import asyncio
+import unittest
+from datetime import datetime, timezone
+from unittest.mock import patch
+
+from dateutil.relativedelta import relativedelta
+
+from bot.utils import time
+from tests.helpers import AsyncMock
+
+
+class TimeTests(unittest.TestCase):
+    """Test helper functions in bot.utils.time."""
+
+    def test_humanize_delta_handle_unknown_units(self):
+        """humanize_delta should be able to handle unknown units, and will not abort."""
+        # Does not abort for unknown units, as the unit name is checked
+        # against the attribute of the relativedelta instance.
+        self.assertEqual(time.humanize_delta(relativedelta(days=2, hours=2), 'elephants', 2), '2 days and 2 hours')
+
+    def test_humanize_delta_handle_high_units(self):
+        """humanize_delta should be able to handle very high units."""
+        # Very high maximum units, but it only ever iterates over
+        # each value the relativedelta might have.
+        self.assertEqual(time.humanize_delta(relativedelta(days=2, hours=2), 'hours', 20), '2 days and 2 hours')
+
+    def test_humanize_delta_should_normal_usage(self):
+        """Testing humanize delta."""
+        test_cases = (
+            (relativedelta(days=2), 'seconds', 1, '2 days'),
+            (relativedelta(days=2, hours=2), 'seconds', 2, '2 days and 2 hours'),
+            (relativedelta(days=2, hours=2), 'seconds', 1, '2 days'),
+            (relativedelta(days=2, hours=2), 'days', 2, '2 days'),
+        )
+
+        for delta, precision, max_units, expected in test_cases:
+            with self.subTest(delta=delta, precision=precision, max_units=max_units, expected=expected):
+                self.assertEqual(time.humanize_delta(delta, precision, max_units), expected)
+
+    def test_humanize_delta_raises_for_invalid_max_units(self):
+        """humanize_delta should raises ValueError('max_units must be positive') for invalid max_units."""
+        test_cases = (-1, 0)
+
+        for max_units in test_cases:
+            with self.subTest(max_units=max_units), self.assertRaises(ValueError) as error:
+                time.humanize_delta(relativedelta(days=2, hours=2), 'hours', max_units)
+                self.assertEqual(str(error), 'max_units must be positive')
+
+    def test_parse_rfc1123(self):
+        """Testing parse_rfc1123."""
+        self.assertEqual(
+            time.parse_rfc1123('Sun, 15 Sep 2019 12:00:00 GMT'),
+            datetime(2019, 9, 15, 12, 0, 0, tzinfo=timezone.utc)
+        )
+
+    def test_format_infraction(self):
+        """Testing format_infraction."""
+        self.assertEqual(time.format_infraction('2019-12-12T00:01:00Z'), '2019-12-12 00:01')
+
+    @patch('asyncio.sleep', new_callable=AsyncMock)
+    def test_wait_until(self, mock):
+        """Testing wait_until."""
+        start = datetime(2019, 1, 1, 0, 0)
+        then = datetime(2019, 1, 1, 0, 10)
+
+        # No return value
+        self.assertIs(asyncio.run(time.wait_until(then, start)), None)
+
+        mock.assert_called_once_with(10 * 60)
+
+    def test_format_infraction_with_duration_none_expiry(self):
+        """format_infraction_with_duration should work for None expiry."""
+        test_cases = (
+            (None, None, None, None),
+
+            # To make sure that date_from and max_units are not touched
+            (None, 'Why hello there!', None, None),
+            (None, None, float('inf'), None),
+            (None, 'Why hello there!', float('inf'), None),
+        )
+
+        for expiry, date_from, max_units, expected in test_cases:
+            with self.subTest(expiry=expiry, date_from=date_from, max_units=max_units, expected=expected):
+                self.assertEqual(time.format_infraction_with_duration(expiry, date_from, max_units), expected)
+
+    def test_format_infraction_with_duration_custom_units(self):
+        """format_infraction_with_duration should work for custom max_units."""
+        test_cases = (
+            ('2019-12-12T00:01:00Z', datetime(2019, 12, 11, 12, 5, 5), 6,
+             '2019-12-12 00:01 (11 hours, 55 minutes and 55 seconds)'),
+            ('2019-11-23T20:09:00Z', datetime(2019, 4, 25, 20, 15), 20,
+             '2019-11-23 20:09 (6 months, 28 days, 23 hours and 54 minutes)')
+        )
+
+        for expiry, date_from, max_units, expected in test_cases:
+            with self.subTest(expiry=expiry, date_from=date_from, max_units=max_units, expected=expected):
+                self.assertEqual(time.format_infraction_with_duration(expiry, date_from, max_units), expected)
+
+    def test_format_infraction_with_duration_normal_usage(self):
+        """format_infraction_with_duration should work for normal usage, across various durations."""
+        test_cases = (
+            ('2019-12-12T00:01:00Z', datetime(2019, 12, 11, 12, 0, 5), 2, '2019-12-12 00:01 (12 hours and 55 seconds)'),
+            ('2019-12-12T00:01:00Z', datetime(2019, 12, 11, 12, 0, 5), 1, '2019-12-12 00:01 (12 hours)'),
+            ('2019-12-12T00:00:00Z', datetime(2019, 12, 11, 23, 59), 2, '2019-12-12 00:00 (1 minute)'),
+            ('2019-11-23T20:09:00Z', datetime(2019, 11, 15, 20, 15), 2, '2019-11-23 20:09 (7 days and 23 hours)'),
+            ('2019-11-23T20:09:00Z', datetime(2019, 4, 25, 20, 15), 2, '2019-11-23 20:09 (6 months and 28 days)'),
+            ('2019-11-23T20:58:00Z', datetime(2019, 11, 23, 20, 53), 2, '2019-11-23 20:58 (5 minutes)'),
+            ('2019-11-24T00:00:00Z', datetime(2019, 11, 23, 23, 59, 0), 2, '2019-11-24 00:00 (1 minute)'),
+            ('2019-11-23T23:59:00Z', datetime(2017, 7, 21, 23, 0), 2, '2019-11-23 23:59 (2 years and 4 months)'),
+            ('2019-11-23T23:59:00Z', datetime(2019, 11, 23, 23, 49, 5), 2,
+             '2019-11-23 23:59 (9 minutes and 55 seconds)'),
+            (None, datetime(2019, 11, 23, 23, 49, 5), 2, None),
+        )
+
+        for expiry, date_from, max_units, expected in test_cases:
+            with self.subTest(expiry=expiry, date_from=date_from, max_units=max_units, expected=expected):
+                self.assertEqual(time.format_infraction_with_duration(expiry, date_from, max_units), expected)
+
+    def test_until_expiration_with_duration_none_expiry(self):
+        """until_expiration should work for None expiry."""
+        test_cases = (
+            (None, None, None, None),
+
+            # To make sure that now and max_units are not touched
+            (None, 'Why hello there!', None, None),
+            (None, None, float('inf'), None),
+            (None, 'Why hello there!', float('inf'), None),
+        )
+
+        for expiry, now, max_units, expected in test_cases:
+            with self.subTest(expiry=expiry, now=now, max_units=max_units, expected=expected):
+                self.assertEqual(time.until_expiration(expiry, now, max_units), expected)
+
+    def test_until_expiration_with_duration_custom_units(self):
+        """until_expiration should work for custom max_units."""
+        test_cases = (
+            ('2019-12-12T00:01:00Z', datetime(2019, 12, 11, 12, 5, 5), 6, '11 hours, 55 minutes and 55 seconds'),
+            ('2019-11-23T20:09:00Z', datetime(2019, 4, 25, 20, 15), 20, '6 months, 28 days, 23 hours and 54 minutes')
+        )
+
+        for expiry, now, max_units, expected in test_cases:
+            with self.subTest(expiry=expiry, now=now, max_units=max_units, expected=expected):
+                self.assertEqual(time.until_expiration(expiry, now, max_units), expected)
+
+    def test_until_expiration_normal_usage(self):
+        """until_expiration should work for normal usage, across various durations."""
+        test_cases = (
+            ('2019-12-12T00:01:00Z', datetime(2019, 12, 11, 12, 0, 5), 2, '12 hours and 55 seconds'),
+            ('2019-12-12T00:01:00Z', datetime(2019, 12, 11, 12, 0, 5), 1, '12 hours'),
+            ('2019-12-12T00:00:00Z', datetime(2019, 12, 11, 23, 59), 2, '1 minute'),
+            ('2019-11-23T20:09:00Z', datetime(2019, 11, 15, 20, 15), 2, '7 days and 23 hours'),
+            ('2019-11-23T20:09:00Z', datetime(2019, 4, 25, 20, 15), 2, '6 months and 28 days'),
+            ('2019-11-23T20:58:00Z', datetime(2019, 11, 23, 20, 53), 2, '5 minutes'),
+            ('2019-11-24T00:00:00Z', datetime(2019, 11, 23, 23, 59, 0), 2, '1 minute'),
+            ('2019-11-23T23:59:00Z', datetime(2017, 7, 21, 23, 0), 2, '2 years and 4 months'),
+            ('2019-11-23T23:59:00Z', datetime(2019, 11, 23, 23, 49, 5), 2, '9 minutes and 55 seconds'),
+            (None, datetime(2019, 11, 23, 23, 49, 5), 2, None),
+        )
+
+        for expiry, now, max_units, expected in test_cases:
+            with self.subTest(expiry=expiry, now=now, max_units=max_units, expected=expected):
+                self.assertEqual(time.until_expiration(expiry, now, max_units), expected)
diff --git a/tests/cogs/sync/test_roles.py b/tests/cogs/sync/test_roles.py
deleted file mode 100644
index c561ba447..000000000
--- a/tests/cogs/sync/test_roles.py
+++ /dev/null
@@ -1,103 +0,0 @@
-from bot.cogs.sync.syncers import Role, get_roles_for_sync
-
-
-def test_get_roles_for_sync_empty_return_for_equal_roles():
-    api_roles = {Role(id=41, name='name', colour=33, permissions=0x8, position=1)}
-    guild_roles = {Role(id=41, name='name', colour=33, permissions=0x8, position=1)}
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (set(), set(), set())
-
-
-def test_get_roles_for_sync_returns_roles_to_update_with_non_id_diff():
-    api_roles = {Role(id=41, name='old name', colour=35, permissions=0x8, position=1)}
-    guild_roles = {Role(id=41, name='new name', colour=33, permissions=0x8, position=2)}
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (
-        set(),
-        guild_roles,
-        set(),
-    )
-
-
-def test_get_roles_only_returns_roles_that_require_update():
-    api_roles = {
-        Role(id=41, name='old name', colour=33, permissions=0x8, position=1),
-        Role(id=53, name='other role', colour=55, permissions=0, position=3)
-    }
-    guild_roles = {
-        Role(id=41, name='new name', colour=35, permissions=0x8, position=2),
-        Role(id=53, name='other role', colour=55, permissions=0, position=3)
-    }
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (
-        set(),
-        {Role(id=41, name='new name', colour=35, permissions=0x8, position=2)},
-        set(),
-    )
-
-
-def test_get_roles_returns_new_roles_in_first_tuple_element():
-    api_roles = {
-        Role(id=41, name='name', colour=35, permissions=0x8, position=1),
-    }
-    guild_roles = {
-        Role(id=41, name='name', colour=35, permissions=0x8, position=1),
-        Role(id=53, name='other role', colour=55, permissions=0, position=2)
-    }
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (
-        {Role(id=53, name='other role', colour=55, permissions=0, position=2)},
-        set(),
-        set(),
-    )
-
-
-def test_get_roles_returns_roles_to_update_and_new_roles():
-    api_roles = {
-        Role(id=41, name='old name', colour=35, permissions=0x8, position=1),
-    }
-    guild_roles = {
-        Role(id=41, name='new name', colour=40, permissions=0x16, position=2),
-        Role(id=53, name='other role', colour=55, permissions=0, position=3)
-    }
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (
-        {Role(id=53, name='other role', colour=55, permissions=0, position=3)},
-        {Role(id=41, name='new name', colour=40, permissions=0x16, position=2)},
-        set(),
-    )
-
-
-def test_get_roles_returns_roles_to_delete():
-    api_roles = {
-        Role(id=41, name='name', colour=35, permissions=0x8, position=1),
-        Role(id=61, name='to delete', colour=99, permissions=0x9, position=2),
-    }
-    guild_roles = {
-        Role(id=41, name='name', colour=35, permissions=0x8, position=1),
-    }
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (
-        set(),
-        set(),
-        {Role(id=61, name='to delete', colour=99, permissions=0x9, position=2)},
-    )
-
-
-def test_get_roles_returns_roles_to_delete_update_and_new_roles():
-    api_roles = {
-        Role(id=41, name='not changed', colour=35, permissions=0x8, position=1),
-        Role(id=61, name='to delete', colour=99, permissions=0x9, position=2),
-        Role(id=71, name='to update', colour=99, permissions=0x9, position=3),
-    }
-    guild_roles = {
-        Role(id=41, name='not changed', colour=35, permissions=0x8, position=1),
-        Role(id=81, name='to create', colour=99, permissions=0x9, position=4),
-        Role(id=71, name='updated', colour=101, permissions=0x5, position=3),
-    }
-
-    assert get_roles_for_sync(guild_roles, api_roles) == (
-        {Role(id=81, name='to create', colour=99, permissions=0x9, position=4)},
-        {Role(id=71, name='updated', colour=101, permissions=0x5, position=3)},
-        {Role(id=61, name='to delete', colour=99, permissions=0x9, position=2)},
-    )
diff --git a/tests/cogs/sync/test_users.py b/tests/cogs/sync/test_users.py
deleted file mode 100644
index a863ae35b..000000000
--- a/tests/cogs/sync/test_users.py
+++ /dev/null
@@ -1,69 +0,0 @@
-from bot.cogs.sync.syncers import User, get_users_for_sync
-
-
-def fake_user(**kwargs):
-    kwargs.setdefault('id', 43)
-    kwargs.setdefault('name', 'bob the test man')
-    kwargs.setdefault('discriminator', 1337)
-    kwargs.setdefault('avatar_hash', None)
-    kwargs.setdefault('roles', (666,))
-    kwargs.setdefault('in_guild', True)
-    return User(**kwargs)
-
-
-def test_get_users_for_sync_returns_nothing_for_empty_params():
-    assert get_users_for_sync({}, {}) == (set(), set())
-
-
-def test_get_users_for_sync_returns_nothing_for_equal_users():
-    api_users = {43: fake_user()}
-    guild_users = {43: fake_user()}
-
-    assert get_users_for_sync(guild_users, api_users) == (set(), set())
-
-
-def test_get_users_for_sync_returns_users_to_update_on_non_id_field_diff():
-    api_users = {43: fake_user()}
-    guild_users = {43: fake_user(name='new fancy name')}
-
-    assert get_users_for_sync(guild_users, api_users) == (
-        set(),
-        {fake_user(name='new fancy name')}
-    )
-
-
-def test_get_users_for_sync_returns_users_to_create_with_new_ids_on_guild():
-    api_users = {43: fake_user()}
-    guild_users = {43: fake_user(), 63: fake_user(id=63)}
-
-    assert get_users_for_sync(guild_users, api_users) == (
-        {fake_user(id=63)},
-        set()
-    )
-
-
-def test_get_users_for_sync_updates_in_guild_field_on_user_leave():
-    api_users = {43: fake_user(), 63: fake_user(id=63)}
-    guild_users = {43: fake_user()}
-
-    assert get_users_for_sync(guild_users, api_users) == (
-        set(),
-        {fake_user(id=63, in_guild=False)}
-    )
-
-
-def test_get_users_for_sync_updates_and_creates_users_as_needed():
-    api_users = {43: fake_user()}
-    guild_users = {63: fake_user(id=63)}
-
-    assert get_users_for_sync(guild_users, api_users) == (
-        {fake_user(id=63)},
-        {fake_user(in_guild=False)}
-    )
-
-
-def test_get_users_for_sync_does_not_duplicate_update_users():
-    api_users = {43: fake_user(in_guild=False)}
-    guild_users = {}
-
-    assert get_users_for_sync(guild_users, api_users) == (set(), set())
diff --git a/tests/cogs/test_antispam.py b/tests/cogs/test_antispam.py
deleted file mode 100644
index 67900b275..000000000
--- a/tests/cogs/test_antispam.py
+++ /dev/null
@@ -1,30 +0,0 @@
-import pytest
-
-from bot.cogs import antispam
-
-
-def test_default_antispam_config_is_valid():
-    validation_errors = antispam.validate_config()
-    assert not validation_errors
-
-
[email protected](
-    ('config', 'expected'),
-    (
-        (
-            {'invalid-rule': {}},
-            {'invalid-rule': "`invalid-rule` is not recognized as an antispam rule."}
-        ),
-        (
-            {'burst': {'interval': 10}},
-            {'burst': "Key `max` is required but not set for rule `burst`"}
-        ),
-        (
-            {'burst': {'max': 10}},
-            {'burst': "Key `interval` is required but not set for rule `burst`"}
-        )
-    )
-)
-def test_invalid_antispam_config_returns_validation_errors(config, expected):
-    validation_errors = antispam.validate_config(config)
-    assert validation_errors == expected
diff --git a/tests/cogs/test_information.py b/tests/cogs/test_information.py
deleted file mode 100644
index 184bd2595..000000000
--- a/tests/cogs/test_information.py
+++ /dev/null
@@ -1,211 +0,0 @@
-import asyncio
-import logging
-import textwrap
-from datetime import datetime
-from unittest.mock import MagicMock, patch
-
-import pytest
-from discord import (
-    CategoryChannel,
-    Colour,
-    Permissions,
-    Role,
-    TextChannel,
-    VoiceChannel,
-)
-
-from bot.cogs import information
-from bot.constants import Emojis
-from bot.decorators import InChannelCheckFailure
-from tests.helpers import AsyncMock
-
-
[email protected]()
-def cog(simple_bot):
-    return information.Information(simple_bot)
-
-
-def role(name: str, id_: int):
-    r = MagicMock()
-    r.name = name
-    r.id = id_
-    r.mention = f'&{name}'
-    return r
-
-
-def member(status: str):
-    m = MagicMock()
-    m.status = status
-    return m
-
-
[email protected]()
-def ctx(moderator_role, simple_ctx):
-    simple_ctx.author.roles = [moderator_role]
-    simple_ctx.guild.created_at = datetime(2001, 1, 1)
-    simple_ctx.send = AsyncMock()
-    return simple_ctx
-
-
-def test_roles_info_command(cog, ctx):
-    everyone_role = MagicMock()
-    everyone_role.name = '@everyone'  # should be excluded in the output
-    ctx.author.roles.append(everyone_role)
-    ctx.guild.roles = ctx.author.roles
-
-    cog.roles_info.can_run = AsyncMock()
-    cog.roles_info.can_run.return_value = True
-
-    coroutine = cog.roles_info.callback(cog, ctx)
-
-    assert asyncio.run(coroutine) is None  # no rval
-    ctx.send.assert_called_once()
-    _, kwargs = ctx.send.call_args
-    embed = kwargs.pop('embed')
-    assert embed.title == "Role information"
-    assert embed.colour == Colour.blurple()
-    assert embed.description == f"`{ctx.guild.roles[0].id}` - {ctx.guild.roles[0].mention}\n"
-    assert embed.footer.text == "Total roles: 1"
-
-
-def test_role_info_command(cog, ctx):
-    dummy_role = MagicMock(spec=Role)
-    dummy_role.name = "Dummy"
-    dummy_role.colour = Colour.blurple()
-    dummy_role.id = 112233445566778899
-    dummy_role.position = 10
-    dummy_role.permissions = Permissions(0)
-    dummy_role.members = [ctx.author]
-
-    admin_role = MagicMock(spec=Role)
-    admin_role.name = "Admin"
-    admin_role.colour = Colour.red()
-    admin_role.id = 998877665544332211
-    admin_role.position = 3
-    admin_role.permissions = Permissions(0)
-    admin_role.members = [ctx.author]
-
-    ctx.guild.roles = [dummy_role, admin_role]
-
-    cog.role_info.can_run = AsyncMock()
-    cog.role_info.can_run.return_value = True
-
-    coroutine = cog.role_info.callback(cog, ctx, dummy_role, admin_role)
-
-    assert asyncio.run(coroutine) is None
-
-    assert ctx.send.call_count == 2
-
-    (_, dummy_kwargs), (_, admin_kwargs) = ctx.send.call_args_list
-
-    dummy_embed = dummy_kwargs["embed"]
-    admin_embed = admin_kwargs["embed"]
-
-    assert dummy_embed.title == "Dummy info"
-    assert dummy_embed.colour == Colour.blurple()
-
-    assert dummy_embed.fields[0].value == str(dummy_role.id)
-    assert dummy_embed.fields[1].value == f"#{dummy_role.colour.value:0>6x}"
-    assert dummy_embed.fields[2].value == "0.63 0.48 218"
-    assert dummy_embed.fields[3].value == "1"
-    assert dummy_embed.fields[4].value == "10"
-    assert dummy_embed.fields[5].value == "0"
-
-    assert admin_embed.title == "Admin info"
-    assert admin_embed.colour == Colour.red()
-
-# There is no argument passed in here that we can use to test,
-# so the return value would change constantly.
-@patch('bot.cogs.information.time_since')
-def test_server_info_command(time_since_patch, cog, ctx, moderator_role):
-    time_since_patch.return_value = '2 days ago'
-
-    ctx.guild.created_at = datetime(2001, 1, 1)
-    ctx.guild.features = ('lemons', 'apples')
-    ctx.guild.region = 'The Moon'
-    ctx.guild.roles = [moderator_role]
-    ctx.guild.channels = [
-        TextChannel(
-            state={},
-            guild=ctx.guild,
-            data={'id': 42, 'name': 'lemons-offering', 'position': 22, 'type': 'text'}
-        ),
-        CategoryChannel(
-            state={},
-            guild=ctx.guild,
-            data={'id': 5125, 'name': 'the-lemon-collection', 'position': 22, 'type': 'category'}
-        ),
-        VoiceChannel(
-            state={},
-            guild=ctx.guild,
-            data={'id': 15290, 'name': 'listen-to-lemon', 'position': 22, 'type': 'voice'}
-        )
-    ]
-    ctx.guild.members = [
-        member('online'), member('online'),
-        member('idle'),
-        member('dnd'), member('dnd'), member('dnd'), member('dnd'),
-        member('offline'), member('offline'), member('offline')
-    ]
-    ctx.guild.member_count = 1_234
-    ctx.guild.icon_url = 'a-lemon.png'
-
-    coroutine = cog.server_info.callback(cog, ctx)
-    assert asyncio.run(coroutine) is None  # no rval
-
-    time_since_patch.assert_called_once_with(ctx.guild.created_at, precision='days')
-    _, kwargs = ctx.send.call_args
-    embed = kwargs.pop('embed')
-    assert embed.colour == Colour.blurple()
-    assert embed.description == textwrap.dedent(f"""
-        **Server information**
-        Created: {time_since_patch.return_value}
-        Voice region: {ctx.guild.region}
-        Features: {', '.join(ctx.guild.features)}
-
-        **Counts**
-        Members: {ctx.guild.member_count:,}
-        Roles: {len(ctx.guild.roles)}
-        Text: 1
-        Voice: 1
-        Channel categories: 1
-
-        **Members**
-        {Emojis.status_online} 2
-        {Emojis.status_idle} 1
-        {Emojis.status_dnd} 4
-        {Emojis.status_offline} 3
-        """)
-    assert embed.thumbnail.url == 'a-lemon.png'
-
-
-def test_user_info_on_other_users_from_non_moderator(ctx, cog):
-    ctx.author = MagicMock()
-    ctx.author.__eq__.return_value = False
-    ctx.author.roles = []
-    coroutine = cog.user_info.callback(cog, ctx, user='scragly')  # skip checks, pass args
-
-    assert asyncio.run(coroutine) is None  # no rval
-    ctx.send.assert_called_once_with(
-        "You may not use this command on users other than yourself."
-    )
-
-
-def test_user_info_in_wrong_channel_from_non_moderator(ctx, cog):
-    ctx.author = MagicMock()
-    ctx.author.__eq__.return_value = False
-    ctx.author.roles = []
-
-    coroutine = cog.user_info.callback(cog, ctx)
-    message = 'Sorry, but you may only use this command within <#267659945086812160>.'
-    with pytest.raises(InChannelCheckFailure, match=message):
-        assert asyncio.run(coroutine) is None  # no rval
-
-
-def test_setup(simple_bot, caplog):
-    information.setup(simple_bot)
-    simple_bot.add_cog.assert_called_once()
-    [record] = caplog.records
-
-    assert record.message == "Cog loaded: Information"
-    assert record.levelno == logging.INFO
diff --git a/tests/cogs/test_security.py b/tests/cogs/test_security.py
deleted file mode 100644
index 1efb460fe..000000000
--- a/tests/cogs/test_security.py
+++ /dev/null
@@ -1,54 +0,0 @@
-import logging
-from unittest.mock import MagicMock
-
-import pytest
-from discord.ext.commands import NoPrivateMessage
-
-from bot.cogs import security
-
-
[email protected]()
-def cog():
-    bot = MagicMock()
-    return security.Security(bot)
-
-
[email protected]()
-def context():
-    return MagicMock()
-
-
-def test_check_additions(cog):
-    cog.bot.check.assert_any_call(cog.check_on_guild)
-    cog.bot.check.assert_any_call(cog.check_not_bot)
-
-
-def test_check_not_bot_for_humans(cog, context):
-    context.author.bot = False
-    assert cog.check_not_bot(context)
-
-
-def test_check_not_bot_for_robots(cog, context):
-    context.author.bot = True
-    assert not cog.check_not_bot(context)
-
-
-def test_check_on_guild_outside_of_guild(cog, context):
-    context.guild = None
-
-    with pytest.raises(NoPrivateMessage, match="This command cannot be used in private messages."):
-        cog.check_on_guild(context)
-
-
-def test_check_on_guild_on_guild(cog, context):
-    context.guild = "lemon's lemonade stand"
-    assert cog.check_on_guild(context)
-
-
-def test_security_cog_load(caplog):
-    bot = MagicMock()
-    security.setup(bot)
-    bot.add_cog.assert_called_once()
-    [record] = caplog.records
-    assert record.message == "Cog loaded: Security"
-    assert record.levelno == logging.INFO
diff --git a/tests/cogs/test_token_remover.py b/tests/cogs/test_token_remover.py
deleted file mode 100644
index 9d46b3a05..000000000
--- a/tests/cogs/test_token_remover.py
+++ /dev/null
@@ -1,133 +0,0 @@
-import asyncio
-from unittest.mock import MagicMock
-
-import pytest
-from discord import Colour
-
-from bot.cogs.token_remover import (
-    DELETION_MESSAGE_TEMPLATE,
-    TokenRemover,
-    setup as setup_cog,
-)
-from bot.constants import Channels, Colours, Event, Icons
-from tests.helpers import AsyncMock
-
-
[email protected]()
-def token_remover():
-    bot = MagicMock()
-    bot.get_cog.return_value = MagicMock()
-    bot.get_cog.return_value.send_log_message = AsyncMock()
-    return TokenRemover(bot=bot)
-
-
[email protected]()
-def message():
-    message = MagicMock()
-    message.author.__str__.return_value = 'lemon'
-    message.author.bot = False
-    message.author.avatar_url_as.return_value = 'picture-lemon.png'
-    message.author.id = 42
-    message.author.mention = '@lemon'
-    message.channel.send = AsyncMock()
-    message.channel.mention = '#lemonade-stand'
-    message.content = ''
-    message.delete = AsyncMock()
-    message.id = 555
-    return message
-
-
[email protected](
-    ('content', 'expected'),
-    (
-        ('MTIz', True),  # 123
-        ('YWJj', False),  # abc
-    )
-)
-def test_is_valid_user_id(content: str, expected: bool):
-    assert TokenRemover.is_valid_user_id(content) is expected
-
-
[email protected](
-    ('content', 'expected'),
-    (
-        ('DN9r_A', True),  # stolen from dapi, thanks to the author of the 'token' tag!
-        ('MTIz', False),  # 123
-    )
-)
-def test_is_valid_timestamp(content: str, expected: bool):
-    assert TokenRemover.is_valid_timestamp(content) is expected
-
-
-def test_mod_log_property(token_remover):
-    token_remover.bot.get_cog.return_value = 'lemon'
-    assert token_remover.mod_log == 'lemon'
-    token_remover.bot.get_cog.assert_called_once_with('ModLog')
-
-
-def test_ignores_bot_messages(token_remover, message):
-    message.author.bot = True
-    coroutine = token_remover.on_message(message)
-    assert asyncio.run(coroutine) is None
-
-
[email protected]('content', ('', 'lemon wins'))
-def test_ignores_messages_without_tokens(token_remover, message, content):
-    message.content = content
-    coroutine = token_remover.on_message(message)
-    assert asyncio.run(coroutine) is None
-
-
[email protected]('content', ('foo.bar.baz', 'x.y.'))
-def test_ignores_invalid_tokens(token_remover, message, content):
-    message.content = content
-    coroutine = token_remover.on_message(message)
-    assert asyncio.run(coroutine) is None
-
-
[email protected](
-    'content, censored_token',
-    (
-        ('MTIz.DN9R_A.xyz', 'MTIz.DN9R_A.xxx'),
-    )
-)
-def test_censors_valid_tokens(
-    token_remover, message, content, censored_token, caplog
-):
-    message.content = content
-    coroutine = token_remover.on_message(message)
-    assert asyncio.run(coroutine) is None  # still no rval
-
-    # asyncio logs some stuff about its reactor, discard it
-    [_, record] = caplog.records
-    assert record.message == (
-        "Censored a seemingly valid token sent by lemon (`42`) in #lemonade-stand, "
-        f"token was `{censored_token}`"
-    )
-
-    message.delete.assert_called_once_with()
-    message.channel.send.assert_called_once_with(
-        DELETION_MESSAGE_TEMPLATE.format(mention='@lemon')
-    )
-    token_remover.bot.get_cog.assert_called_with('ModLog')
-    message.author.avatar_url_as.assert_called_once_with(static_format='png')
-
-    mod_log = token_remover.bot.get_cog.return_value
-    mod_log.ignore.assert_called_once_with(Event.message_delete, message.id)
-    mod_log.send_log_message.assert_called_once_with(
-        icon_url=Icons.token_removed,
-        colour=Colour(Colours.soft_red),
-        title="Token removed!",
-        text=record.message,
-        thumbnail='picture-lemon.png',
-        channel_id=Channels.mod_alerts
-    )
-
-
-def test_setup(caplog):
-    bot = MagicMock()
-    setup_cog(bot)
-    [record] = caplog.records
-
-    bot.add_cog.assert_called_once()
-    assert record.message == "Cog loaded: TokenRemover"
diff --git a/tests/conftest.py b/tests/conftest.py
deleted file mode 100644
index d3de4484d..000000000
--- a/tests/conftest.py
+++ /dev/null
@@ -1,32 +0,0 @@
-from unittest.mock import MagicMock
-
-import pytest
-
-from bot.constants import Roles
-from tests.helpers import AsyncMock
-
-
[email protected]()
-def moderator_role():
-    mock = MagicMock()
-    mock.id = Roles.moderator
-    mock.name = 'Moderator'
-    mock.mention = f'&{mock.name}'
-    return mock
-
-
[email protected]()
-def simple_bot():
-    mock = MagicMock()
-    mock._before_invoke = AsyncMock()
-    mock._after_invoke = AsyncMock()
-    mock.can_run = AsyncMock()
-    mock.can_run.return_value = True
-    return mock
-
-
[email protected]()
-def simple_ctx(simple_bot):
-    mock = MagicMock()
-    mock.bot = simple_bot
-    return mock
diff --git a/tests/helpers.py b/tests/helpers.py
index 25059fa3a..5df796c23 100644
--- a/tests/helpers.py
+++ b/tests/helpers.py
@@ -1,27 +1,34 @@
+from __future__ import annotations
+
 import asyncio
+import collections
 import functools
-from unittest.mock import MagicMock
+import inspect
+import itertools
+import logging
+import unittest.mock
+from typing import Any, Iterable, Optional
 
+import discord
+from discord.ext.commands import Context
 
-__all__ = ('AsyncMock', 'async_test')
+from bot.bot import Bot
 
 
-# TODO: Remove me on 3.8
-# Allows you to mock a coroutine. Since the default `__call__` of `MagicMock`
-# is not a coroutine, trying to mock a coroutine with it will result in errors
-# as the default `__call__` is not awaitable. Use this class for monkeypatching
-# coroutines instead.
-class AsyncMock(MagicMock):
-    async def __call__(self, *args, **kwargs):
-        return super(AsyncMock, self).__call__(*args, **kwargs)
+for logger in logging.Logger.manager.loggerDict.values():
+    # Set all loggers to CRITICAL by default to prevent screen clutter during testing
+
+    if not isinstance(logger, logging.Logger):
+        # There might be some logging.PlaceHolder objects in there
+        continue
+
+    logger.setLevel(logging.CRITICAL)
 
 
 def async_test(wrapped):
     """
     Run a test case via asyncio.
-
     Example:
-
         >>> @async_test
         ... async def lemon_wins():
         ...     assert True
@@ -31,3 +38,490 @@ def async_test(wrapped):
     def wrapper(*args, **kwargs):
         return asyncio.run(wrapped(*args, **kwargs))
     return wrapper
+
+
+class HashableMixin(discord.mixins.EqualityComparable):
+    """
+    Mixin that provides similar hashing and equality functionality as discord.py's `Hashable` mixin.
+
+    Note: discord.py`s `Hashable` mixin bit-shifts `self.id` (`>> 22`); to prevent hash-collisions
+    for the relative small `id` integers we generally use in tests, this bit-shift is omitted.
+    """
+
+    def __hash__(self):
+        return self.id
+
+
+class ColourMixin:
+    """A mixin for Mocks that provides the aliasing of color->colour like discord.py does."""
+
+    @property
+    def color(self) -> discord.Colour:
+        return self.colour
+
+    @color.setter
+    def color(self, color: discord.Colour) -> None:
+        self.colour = color
+
+
+class CustomMockMixin:
+    """
+    Provides common functionality for our custom Mock types.
+
+    The cooperative `__init__` automatically creates `AsyncMock` attributes for every coroutine
+    function `inspect` detects in the `spec` instance we provide. In addition, this mixin takes care
+    of making sure child mocks are instantiated with the correct class. By default, the mock of the
+    children will be `unittest.mock.MagicMock`, but this can be overwritten by setting the attribute
+    `child_mock_type` on the custom mock inheriting from this mixin.
+    """
+
+    child_mock_type = unittest.mock.MagicMock
+    discord_id = itertools.count(0)
+
+    def __init__(self, spec_set: Any = None, **kwargs):
+        name = kwargs.pop('name', None)  # `name` has special meaning for Mock classes, so we need to set it manually.
+        super().__init__(spec_set=spec_set, **kwargs)
+
+        if name:
+            self.name = name
+        if spec_set:
+            self._extract_coroutine_methods_from_spec_instance(spec_set)
+
+    def _get_child_mock(self, **kw):
+        """
+        Overwrite of the `_get_child_mock` method to stop the propagation of our custom mock classes.
+
+        Mock objects automatically create children when you access an attribute or call a method on them. By default,
+        the class of these children is the type of the parent itself. However, this would mean that the children created
+        for our custom mock types would also be instances of that custom mock type. This is not desirable, as attributes
+        of, e.g., a `Bot` object are not `Bot` objects themselves. The Python docs for `unittest.mock` hint that
+        overwriting this method is the best way to deal with that.
+
+        This override will look for an attribute called `child_mock_type` and use that as the type of the child mock.
+        """
+        klass = self.child_mock_type
+
+        if self._mock_sealed:
+            attribute = "." + kw["name"] if "name" in kw else "()"
+            mock_name = self._extract_mock_name() + attribute
+            raise AttributeError(mock_name)
+
+        return klass(**kw)
+
+    def _extract_coroutine_methods_from_spec_instance(self, source: Any) -> None:
+        """Automatically detect coroutine functions in `source` and set them as AsyncMock attributes."""
+        for name, _method in inspect.getmembers(source, inspect.iscoroutinefunction):
+            setattr(self, name, AsyncMock())
+
+
+# TODO: Remove me in Python 3.8
+class AsyncMock(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock async callables.
+
+    Python 3.8 will introduce an AsyncMock class in the standard library that will have some more
+    features; this stand-in only overwrites the `__call__` method to an async version.
+    """
+
+    async def __call__(self, *args, **kwargs):
+        return super().__call__(*args, **kwargs)
+
+
+class AsyncIteratorMock:
+    """
+    A class to mock asynchronous iterators.
+
+    This allows async for, which is used in certain Discord.py objects. For example,
+    an async iterator is returned by the Reaction.users() method.
+    """
+
+    def __init__(self, iterable: Iterable = None):
+        if iterable is None:
+            iterable = []
+
+        self.iter = iter(iterable)
+        self.iterable = iterable
+
+        self.call_count = 0
+
+    def __aiter__(self):
+        return self
+
+    async def __anext__(self):
+        try:
+            return next(self.iter)
+        except StopIteration:
+            raise StopAsyncIteration
+
+    def __call__(self):
+        """
+        Keeps track of the number of times an instance has been called.
+
+        This is useful, since it typically shows that the iterator has actually been used somewhere after we have
+        instantiated the mock for an attribute that normally returns an iterator when called.
+        """
+        self.call_count += 1
+        return self
+
+    @property
+    def return_value(self):
+        """Makes `self.iterable` accessible as self.return_value."""
+        return self.iterable
+
+    @return_value.setter
+    def return_value(self, iterable):
+        """Stores the `return_value` as `self.iterable` and its iterator as `self.iter`."""
+        self.iter = iter(iterable)
+        self.iterable = iterable
+
+    def assert_called(self):
+        """Asserts if the AsyncIteratorMock instance has been called at least once."""
+        if self.call_count == 0:
+            raise AssertionError("Expected AsyncIteratorMock to have been called.")
+
+    def assert_called_once(self):
+        """Asserts if the AsyncIteratorMock instance has been called exactly once."""
+        if self.call_count != 1:
+            raise AssertionError(
+                f"Expected AsyncIteratorMock to have been called once. Called {self.call_count} times."
+            )
+
+    def assert_not_called(self):
+        """Asserts if the AsyncIteratorMock instance has not been called."""
+        if self.call_count != 0:
+            raise AssertionError(
+                f"Expected AsyncIteratorMock to not have been called once. Called {self.call_count} times."
+            )
+
+    def reset_mock(self):
+        """Resets the call count, but not the return value or iterator."""
+        self.call_count = 0
+
+
+# Create a guild instance to get a realistic Mock of `discord.Guild`
+guild_data = {
+    'id': 1,
+    'name': 'guild',
+    'region': 'Europe',
+    'verification_level': 2,
+    'default_notications': 1,
+    'afk_timeout': 100,
+    'icon': "icon.png",
+    'banner': 'banner.png',
+    'mfa_level': 1,
+    'splash': 'splash.png',
+    'system_channel_id': 464033278631084042,
+    'description': 'mocking is fun',
+    'max_presences': 10_000,
+    'max_members': 100_000,
+    'preferred_locale': 'UTC',
+    'owner_id': 1,
+    'afk_channel_id': 464033278631084042,
+}
+guild_instance = discord.Guild(data=guild_data, state=unittest.mock.MagicMock())
+
+
+class MockGuild(CustomMockMixin, unittest.mock.Mock, HashableMixin):
+    """
+    A `Mock` subclass to mock `discord.Guild` objects.
+
+    A MockGuild instance will follow the specifications of a `discord.Guild` instance. This means
+    that if the code you're testing tries to access an attribute or method that normally does not
+    exist for a `discord.Guild` object this will raise an `AttributeError`. This is to make sure our
+    tests fail if the code we're testing uses a `discord.Guild` object in the wrong way.
+
+    One restriction of that is that if the code tries to access an attribute that normally does not
+    exist for `discord.Guild` instance but was added dynamically, this will raise an exception with
+    the mocked object. To get around that, you can set the non-standard attribute explicitly for the
+    instance of `MockGuild`:
+
+    >>> guild = MockGuild()
+    >>> guild.attribute_that_normally_does_not_exist = unittest.mock.MagicMock()
+
+    In addition to attribute simulation, mocked guild object will pass an `isinstance` check against
+    `discord.Guild`:
+
+    >>> guild = MockGuild()
+    >>> isinstance(guild, discord.Guild)
+    True
+
+    For more info, see the `Mocking` section in `tests/README.md`.
+    """
+    def __init__(self, roles: Optional[Iterable[MockRole]] = None, **kwargs) -> None:
+        default_kwargs = {'id': next(self.discord_id), 'members': []}
+        super().__init__(spec_set=guild_instance, **collections.ChainMap(kwargs, default_kwargs))
+
+        self.roles = [MockRole(name="@everyone", position=1, id=0)]
+        if roles:
+            self.roles.extend(roles)
+
+
+# Create a Role instance to get a realistic Mock of `discord.Role`
+role_data = {'name': 'role', 'id': 1}
+role_instance = discord.Role(guild=guild_instance, state=unittest.mock.MagicMock(), data=role_data)
+
+
+class MockRole(CustomMockMixin, unittest.mock.Mock, ColourMixin, HashableMixin):
+    """
+    A Mock subclass to mock `discord.Role` objects.
+
+    Instances of this class will follow the specifications of `discord.Role` instances. For more
+    information, see the `MockGuild` docstring.
+    """
+    def __init__(self, **kwargs) -> None:
+        default_kwargs = {'id': next(self.discord_id), 'name': 'role', 'position': 1}
+        super().__init__(spec_set=role_instance, **collections.ChainMap(kwargs, default_kwargs))
+
+        if 'mention' not in kwargs:
+            self.mention = f'&{self.name}'
+
+    def __lt__(self, other):
+        """Simplified position-based comparisons similar to those of `discord.Role`."""
+        return self.position < other.position
+
+
+# Create a Member instance to get a realistic Mock of `discord.Member`
+member_data = {'user': 'lemon', 'roles': [1]}
+state_mock = unittest.mock.MagicMock()
+member_instance = discord.Member(data=member_data, guild=guild_instance, state=state_mock)
+
+
+class MockMember(CustomMockMixin, unittest.mock.Mock, ColourMixin, HashableMixin):
+    """
+    A Mock subclass to mock Member objects.
+
+    Instances of this class will follow the specifications of `discord.Member` instances. For more
+    information, see the `MockGuild` docstring.
+    """
+    def __init__(self, roles: Optional[Iterable[MockRole]] = None, **kwargs) -> None:
+        default_kwargs = {'name': 'member', 'id': next(self.discord_id), 'bot': False}
+        super().__init__(spec_set=member_instance, **collections.ChainMap(kwargs, default_kwargs))
+
+        self.roles = [MockRole(name="@everyone", position=1, id=0)]
+        if roles:
+            self.roles.extend(roles)
+
+        if 'mention' not in kwargs:
+            self.mention = f"@{self.name}"
+
+
+# Create a User instance to get a realistic Mock of `discord.User`
+user_instance = discord.User(data=unittest.mock.MagicMock(), state=unittest.mock.MagicMock())
+
+
+class MockUser(CustomMockMixin, unittest.mock.Mock, ColourMixin, HashableMixin):
+    """
+    A Mock subclass to mock User objects.
+
+    Instances of this class will follow the specifications of `discord.User` instances. For more
+    information, see the `MockGuild` docstring.
+    """
+    def __init__(self, **kwargs) -> None:
+        default_kwargs = {'name': 'user', 'id': next(self.discord_id), 'bot': False}
+        super().__init__(spec_set=user_instance, **collections.ChainMap(kwargs, default_kwargs))
+
+        if 'mention' not in kwargs:
+            self.mention = f"@{self.name}"
+
+
+# Create a Bot instance to get a realistic MagicMock of `discord.ext.commands.Bot`
+bot_instance = Bot(command_prefix=unittest.mock.MagicMock())
+bot_instance.http_session = None
+bot_instance.api_client = None
+
+
+class MockBot(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Bot objects.
+
+    Instances of this class will follow the specifications of `discord.ext.commands.Bot` instances.
+    For more information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=bot_instance, **kwargs)
+
+        # self.wait_for is *not* a coroutine function, but returns a coroutine nonetheless and
+        # and should therefore be awaited. (The documentation calls it a coroutine as well, which
+        # is technically incorrect, since it's a regular def.)
+        self.wait_for = AsyncMock()
+
+        # Since calling `create_task` on our MockBot does not actually schedule the coroutine object
+        # as a task in the asyncio loop, this `side_effect` calls `close()` on the coroutine object
+        # to prevent "has not been awaited"-warnings.
+        self.loop.create_task.side_effect = lambda coroutine: coroutine.close()
+
+
+# Create a TextChannel instance to get a realistic MagicMock of `discord.TextChannel`
+channel_data = {
+    'id': 1,
+    'type': 'TextChannel',
+    'name': 'channel',
+    'parent_id': 1234567890,
+    'topic': 'topic',
+    'position': 1,
+    'nsfw': False,
+    'last_message_id': 1,
+}
+state = unittest.mock.MagicMock()
+guild = unittest.mock.MagicMock()
+channel_instance = discord.TextChannel(state=state, guild=guild, data=channel_data)
+
+
+class MockTextChannel(CustomMockMixin, unittest.mock.Mock, HashableMixin):
+    """
+    A MagicMock subclass to mock TextChannel objects.
+
+    Instances of this class will follow the specifications of `discord.TextChannel` instances. For
+    more information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, name: str = 'channel', channel_id: int = 1, **kwargs) -> None:
+        default_kwargs = {'id': next(self.discord_id), 'name': 'channel', 'guild': MockGuild()}
+        super().__init__(spec_set=channel_instance, **collections.ChainMap(kwargs, default_kwargs))
+
+        if 'mention' not in kwargs:
+            self.mention = f"#{self.name}"
+
+
+# Create a Message instance to get a realistic MagicMock of `discord.Message`
+message_data = {
+    'id': 1,
+    'webhook_id': 431341013479718912,
+    'attachments': [],
+    'embeds': [],
+    'application': 'Python Discord',
+    'activity': 'mocking',
+    'channel': unittest.mock.MagicMock(),
+    'edited_timestamp': '2019-10-14T15:33:48+00:00',
+    'type': 'message',
+    'pinned': False,
+    'mention_everyone': False,
+    'tts': None,
+    'content': 'content',
+    'nonce': None,
+}
+state = unittest.mock.MagicMock()
+channel = unittest.mock.MagicMock()
+message_instance = discord.Message(state=state, channel=channel, data=message_data)
+
+
+# Create a Context instance to get a realistic MagicMock of `discord.ext.commands.Context`
+context_instance = Context(message=unittest.mock.MagicMock(), prefix=unittest.mock.MagicMock())
+
+
+class MockContext(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Context objects.
+
+    Instances of this class will follow the specifications of `discord.ext.commands.Context`
+    instances. For more information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=context_instance, **kwargs)
+        self.bot = kwargs.get('bot', MockBot())
+        self.guild = kwargs.get('guild', MockGuild())
+        self.author = kwargs.get('author', MockMember())
+        self.channel = kwargs.get('channel', MockTextChannel())
+
+
+attachment_instance = discord.Attachment(data=unittest.mock.MagicMock(id=1), state=unittest.mock.MagicMock())
+
+
+class MockAttachment(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Attachment objects.
+
+    Instances of this class will follow the specifications of `discord.Attachment` instances. For
+    more information, see the `MockGuild` docstring.
+    """
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=attachment_instance, **kwargs)
+
+
+class MockMessage(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Message objects.
+
+    Instances of this class will follow the specifications of `discord.Message` instances. For more
+    information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        default_kwargs = {'attachments': []}
+        super().__init__(spec_set=message_instance, **collections.ChainMap(kwargs, default_kwargs))
+        self.author = kwargs.get('author', MockMember())
+        self.channel = kwargs.get('channel', MockTextChannel())
+
+
+emoji_data = {'require_colons': True, 'managed': True, 'id': 1, 'name': 'hyperlemon'}
+emoji_instance = discord.Emoji(guild=MockGuild(), state=unittest.mock.MagicMock(), data=emoji_data)
+
+
+class MockEmoji(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Emoji objects.
+
+    Instances of this class will follow the specifications of `discord.Emoji` instances. For more
+    information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=emoji_instance, **kwargs)
+        self.guild = kwargs.get('guild', MockGuild())
+
+
+partial_emoji_instance = discord.PartialEmoji(animated=False, name='guido')
+
+
+class MockPartialEmoji(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock PartialEmoji objects.
+
+    Instances of this class will follow the specifications of `discord.PartialEmoji` instances. For
+    more information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=partial_emoji_instance, **kwargs)
+
+
+reaction_instance = discord.Reaction(message=MockMessage(), data={'me': True}, emoji=MockEmoji())
+
+
+class MockReaction(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Reaction objects.
+
+    Instances of this class will follow the specifications of `discord.Reaction` instances. For
+    more information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=reaction_instance, **kwargs)
+        self.emoji = kwargs.get('emoji', MockEmoji())
+        self.message = kwargs.get('message', MockMessage())
+        self.users = AsyncIteratorMock(kwargs.get('users', []))
+
+
+webhook_instance = discord.Webhook(data=unittest.mock.MagicMock(), adapter=unittest.mock.MagicMock())
+
+
+class MockAsyncWebhook(CustomMockMixin, unittest.mock.MagicMock):
+    """
+    A MagicMock subclass to mock Webhook objects using an AsyncWebhookAdapter.
+
+    Instances of this class will follow the specifications of `discord.Webhook` instances. For
+    more information, see the `MockGuild` docstring.
+    """
+
+    def __init__(self, **kwargs) -> None:
+        super().__init__(spec_set=webhook_instance, **kwargs)
+
+        # Because Webhooks can also use a synchronous "WebhookAdapter", the methods are not defined
+        # as coroutines. That's why we need to set the methods manually.
+        self.send = AsyncMock()
+        self.edit = AsyncMock()
+        self.delete = AsyncMock()
+        self.execute = AsyncMock()
diff --git a/tests/rules/test_attachments.py b/tests/rules/test_attachments.py
deleted file mode 100644
index 6f025b3cb..000000000
--- a/tests/rules/test_attachments.py
+++ /dev/null
@@ -1,52 +0,0 @@
-import asyncio
-from dataclasses import dataclass
-from typing import Any, List
-
-import pytest
-
-from bot.rules import attachments
-
-
-# Using `MagicMock` sadly doesn't work for this usecase
-# since it's __eq__ compares the MagicMock's ID. We just
-# want to compare the actual attributes we set.
-@dataclass
-class FakeMessage:
-    author: str
-    attachments: List[Any]
-
-
-def msg(total_attachments: int):
-    return FakeMessage(author='lemon', attachments=list(range(total_attachments)))
-
-
[email protected](
-    'messages',
-    (
-        (msg(0), msg(0), msg(0)),
-        (msg(2), msg(2)),
-        (msg(0),),
-    )
-)
-def test_allows_messages_without_too_many_attachments(messages):
-    last_message, *recent_messages = messages
-    coro = attachments.apply(last_message, recent_messages, {'max': 5})
-    assert asyncio.run(coro) is None
-
-
[email protected](
-    ('messages', 'relevant_messages', 'total'),
-    (
-        ((msg(4), msg(0), msg(6)), [msg(4), msg(6)], 10),
-        ((msg(6),), [msg(6)], 6),
-        ((msg(1),) * 6, [msg(1)] * 6, 6),
-    )
-)
-def test_disallows_messages_with_too_many_attachments(messages, relevant_messages, total):
-    last_message, *recent_messages = messages
-    coro = attachments.apply(last_message, recent_messages, {'max': 5})
-    assert asyncio.run(coro) == (
-        f"sent {total} attachments in 5s",
-        ('lemon',),
-        relevant_messages
-    )
diff --git a/tests/test_api.py b/tests/test_api.py
deleted file mode 100644
index ce69ef187..000000000
--- a/tests/test_api.py
+++ /dev/null
@@ -1,106 +0,0 @@
-import logging
-from unittest.mock import MagicMock, patch
-
-import pytest
-
-from bot import api
-from tests.helpers import async_test
-
-
-def test_loop_is_not_running_by_default():
-    assert not api.loop_is_running()
-
-
-@async_test
-async def test_loop_is_running_in_async_test():
-    assert api.loop_is_running()
-
-
[email protected]()
-def error_api_response():
-    response = MagicMock()
-    response.status = 999
-    return response
-
-
[email protected]()
-def api_log_handler():
-    return api.APILoggingHandler(None)
-
-
[email protected]()
-def debug_log_record():
-    return logging.LogRecord(
-        name='my.logger', level=logging.DEBUG,
-        pathname='my/logger.py', lineno=666,
-        msg="Lemon wins", args=(),
-        exc_info=None
-    )
-
-
-def test_response_code_error_default_initialization(error_api_response):
-    error = api.ResponseCodeError(response=error_api_response)
-    assert error.status is error_api_response.status
-    assert not error.response_json
-    assert not error.response_text
-    assert error.response is error_api_response
-
-
-def test_response_code_error_default_representation(error_api_response):
-    error = api.ResponseCodeError(response=error_api_response)
-    assert str(error) == f"Status: {error_api_response.status} Response: "
-
-
-def test_response_code_error_representation_with_nonempty_response_json(error_api_response):
-    error = api.ResponseCodeError(
-        response=error_api_response,
-        response_json={'hello': 'world'}
-    )
-    assert str(error) == f"Status: {error_api_response.status} Response: {{'hello': 'world'}}"
-
-
-def test_response_code_error_representation_with_nonempty_response_text(error_api_response):
-    error = api.ResponseCodeError(
-        response=error_api_response,
-        response_text='Lemon will eat your soul'
-    )
-    assert str(error) == f"Status: {error_api_response.status} Response: Lemon will eat your soul"
-
-
-@patch('bot.api.APILoggingHandler.ship_off')
-def test_emit_appends_to_queue_with_stopped_event_loop(
-    ship_off_patch, api_log_handler, debug_log_record
-):
-    # This is a coroutine so returns something we should await,
-    # but asyncio complains about that. To ease testing, we patch
-    # `ship_off` to just return a regular value instead.
-    ship_off_patch.return_value = 42
-    api_log_handler.emit(debug_log_record)
-
-    assert api_log_handler.queue == [42]
-
-
-def test_emit_ignores_less_than_debug(debug_log_record, api_log_handler):
-    debug_log_record.levelno = logging.DEBUG - 5
-    api_log_handler.emit(debug_log_record)
-    assert not api_log_handler.queue
-
-
-def test_schedule_queued_tasks_for_empty_queue(api_log_handler, caplog):
-    api_log_handler.schedule_queued_tasks()
-    # Logs when tasks are scheduled
-    assert not caplog.records
-
-
-@patch('asyncio.create_task')
-def test_schedule_queued_tasks_for_nonempty_queue(create_task_patch, api_log_handler, caplog):
-    api_log_handler.queue = [555]
-    api_log_handler.schedule_queued_tasks()
-    assert not api_log_handler.queue
-    create_task_patch.assert_called_once_with(555)
-
-    [record] = caplog.records
-    assert record.message == "Scheduled 1 pending logging tasks."
-    assert record.levelno == logging.DEBUG
-    assert record.name == 'bot.api'
-    assert record.__dict__['via_handler']
diff --git a/tests/test_base.py b/tests/test_base.py
new file mode 100644
index 000000000..a16e2af8f
--- /dev/null
+++ b/tests/test_base.py
@@ -0,0 +1,91 @@
+import logging
+import unittest
+import unittest.mock
+
+
+from tests.base import LoggingTestCase, _CaptureLogHandler
+
+
+class LoggingTestCaseTests(unittest.TestCase):
+    """Tests for the LoggingTestCase."""
+
+    @classmethod
+    def setUpClass(cls):
+        cls.log = logging.getLogger(__name__)
+
+    def test_assert_not_logs_does_not_raise_with_no_logs(self):
+        """Test if LoggingTestCase.assertNotLogs does not raise when no logs were emitted."""
+        try:
+            with LoggingTestCase.assertNotLogs(self, level=logging.DEBUG):
+                pass
+        except AssertionError:
+            self.fail("`self.assertNotLogs` raised an AssertionError when it should not!")
+
+    @unittest.mock.patch("tests.base.LoggingTestCase.assertNotLogs")
+    def test_the_test_function_assert_not_logs_does_not_raise_with_no_logs(self, assertNotLogs):
+        """Test if test_assert_not_logs_does_not_raise_with_no_logs captures exception correctly."""
+        assertNotLogs.return_value = iter([None])
+        assertNotLogs.side_effect = AssertionError
+
+        message = "`self.assertNotLogs` raised an AssertionError when it should not!"
+        with self.assertRaises(AssertionError, msg=message):
+            self.test_assert_not_logs_does_not_raise_with_no_logs()
+
+    def test_assert_not_logs_raises_correct_assertion_error_when_logs_are_emitted(self):
+        """Test if LoggingTestCase.assertNotLogs raises AssertionError when logs were emitted."""
+        msg_regex = (
+            r"1 logs of DEBUG or higher were triggered on root:\n"
+            r'<LogRecord: tests\.test_base, [\d]+, .+/tests/test_base\.py, [\d]+, "Log!">'
+        )
+        with self.assertRaisesRegex(AssertionError, msg_regex):
+            with LoggingTestCase.assertNotLogs(self, level=logging.DEBUG):
+                self.log.debug("Log!")
+
+    def test_assert_not_logs_reraises_unexpected_exception_in_managed_context(self):
+        """Test if LoggingTestCase.assertNotLogs reraises an unexpected exception."""
+        with self.assertRaises(ValueError, msg="test exception"):
+            with LoggingTestCase.assertNotLogs(self, level=logging.DEBUG):
+                raise ValueError("test exception")
+
+    def test_assert_not_logs_restores_old_logging_settings(self):
+        """Test if LoggingTestCase.assertNotLogs reraises an unexpected exception."""
+        old_handlers = self.log.handlers[:]
+        old_level = self.log.level
+        old_propagate = self.log.propagate
+
+        with LoggingTestCase.assertNotLogs(self, level=logging.DEBUG):
+            pass
+
+        self.assertEqual(self.log.handlers, old_handlers)
+        self.assertEqual(self.log.level, old_level)
+        self.assertEqual(self.log.propagate, old_propagate)
+
+    def test_logging_test_case_works_with_logger_instance(self):
+        """Test if the LoggingTestCase captures logging for provided logger."""
+        log = logging.getLogger("new_logger")
+        with self.assertRaises(AssertionError):
+            with LoggingTestCase.assertNotLogs(self, logger=log):
+                log.info("Hello, this should raise an AssertionError")
+
+    def test_logging_test_case_respects_alternative_logger(self):
+        """Test if LoggingTestCase only checks the provided logger."""
+        log_one = logging.getLogger("log one")
+        log_two = logging.getLogger("log two")
+        with LoggingTestCase.assertNotLogs(self, logger=log_one):
+            log_two.info("Hello, this should not raise an AssertionError")
+
+    def test_logging_test_case_respects_logging_level(self):
+        """Test if LoggingTestCase does not raise for a logging level lower than provided."""
+        with LoggingTestCase.assertNotLogs(self, level=logging.CRITICAL):
+            self.log.info("Hello, this should raise an AssertionError")
+
+    def test_capture_log_handler_default_initialization(self):
+        """Test if the _CaptureLogHandler is initialized properly."""
+        handler = _CaptureLogHandler()
+        self.assertFalse(handler.records)
+
+    def test_capture_log_handler_saves_record_on_emit(self):
+        """Test if the _CaptureLogHandler saves the log record when it's emitted."""
+        handler = _CaptureLogHandler()
+        handler.emit("Log message")
+        self.assertIn("Log message", handler.records)
diff --git a/tests/test_constants.py b/tests/test_constants.py
deleted file mode 100644
index e4a29d994..000000000
--- a/tests/test_constants.py
+++ /dev/null
@@ -1,23 +0,0 @@
-import inspect
-
-import pytest
-
-from bot import constants
-
-
[email protected](
-    'section',
-    (
-        cls
-        for (name, cls) in inspect.getmembers(constants)
-        if hasattr(cls, 'section') and isinstance(cls, type)
-    )
-)
-def test_section_configuration_matches_typespec(section):
-    for (name, annotation) in section.__annotations__.items():
-        value = getattr(section, name)
-
-        if getattr(annotation, '_name', None) in ('Dict', 'List'):
-            pytest.skip("Cannot validate containers yet")
-
-        assert isinstance(value, annotation)
diff --git a/tests/test_converters.py b/tests/test_converters.py
deleted file mode 100644
index f69995ec6..000000000
--- a/tests/test_converters.py
+++ /dev/null
@@ -1,264 +0,0 @@
-import asyncio
-import datetime
-from unittest.mock import MagicMock, patch
-
-import pytest
-from dateutil.relativedelta import relativedelta
-from discord.ext.commands import BadArgument
-
-from bot.converters import (
-    Duration,
-    ISODateTime,
-    TagContentConverter,
-    TagNameConverter,
-    ValidPythonIdentifier,
-)
-
-
[email protected](
-    ('value', 'expected'),
-    (
-        ('hello', 'hello'),
-        ('  h ello  ', 'h ello')
-    )
-)
-def test_tag_content_converter_for_valid(value: str, expected: str):
-    assert asyncio.run(TagContentConverter.convert(None, value)) == expected
-
-
[email protected](
-    ('value', 'expected'),
-    (
-        ('', "Tag contents should not be empty, or filled with whitespace."),
-        ('   ', "Tag contents should not be empty, or filled with whitespace.")
-    )
-)
-def test_tag_content_converter_for_invalid(value: str, expected: str):
-    context = MagicMock()
-    context.author = 'bob'
-
-    with pytest.raises(BadArgument, match=expected):
-        asyncio.run(TagContentConverter.convert(context, value))
-
-
[email protected](
-    ('value', 'expected'),
-    (
-        ('tracebacks', 'tracebacks'),
-        ('Tracebacks', 'tracebacks'),
-        ('  Tracebacks  ', 'tracebacks'),
-    )
-)
-def test_tag_name_converter_for_valid(value: str, expected: str):
-    assert asyncio.run(TagNameConverter.convert(None, value)) == expected
-
-
[email protected](
-    ('value', 'expected'),
-    (
-        ('👋', "Don't be ridiculous, you can't use that character!"),
-        ('', "Tag names should not be empty, or filled with whitespace."),
-        ('  ', "Tag names should not be empty, or filled with whitespace."),
-        ('42', "Tag names can't be numbers."),
-        # Escape question mark as this is evaluated as regular expression.
-        ('x' * 128, r"Are you insane\? That's way too long!"),
-    )
-)
-def test_tag_name_converter_for_invalid(value: str, expected: str):
-    context = MagicMock()
-    context.author = 'bob'
-
-    with pytest.raises(BadArgument, match=expected):
-        asyncio.run(TagNameConverter.convert(context, value))
-
-
[email protected]('value', ('foo', 'lemon'))
-def test_valid_python_identifier_for_valid(value: str):
-    assert asyncio.run(ValidPythonIdentifier.convert(None, value)) == value
-
-
[email protected]('value', ('nested.stuff', '#####'))
-def test_valid_python_identifier_for_invalid(value: str):
-    with pytest.raises(BadArgument, match=f'`{value}` is not a valid Python identifier'):
-        asyncio.run(ValidPythonIdentifier.convert(None, value))
-
-
-FIXED_UTC_NOW = datetime.datetime.fromisoformat('2019-01-01T00:00:00')
-
-
[email protected](
-    params=(
-        # Simple duration strings
-        ('1Y', {"years": 1}),
-        ('1y', {"years": 1}),
-        ('1year', {"years": 1}),
-        ('1years', {"years": 1}),
-        ('1m', {"months": 1}),
-        ('1month', {"months": 1}),
-        ('1months', {"months": 1}),
-        ('1w', {"weeks": 1}),
-        ('1W', {"weeks": 1}),
-        ('1week', {"weeks": 1}),
-        ('1weeks', {"weeks": 1}),
-        ('1d', {"days": 1}),
-        ('1D', {"days": 1}),
-        ('1day', {"days": 1}),
-        ('1days', {"days": 1}),
-        ('1h', {"hours": 1}),
-        ('1H', {"hours": 1}),
-        ('1hour', {"hours": 1}),
-        ('1hours', {"hours": 1}),
-        ('1M', {"minutes": 1}),
-        ('1minute', {"minutes": 1}),
-        ('1minutes', {"minutes": 1}),
-        ('1s', {"seconds": 1}),
-        ('1S', {"seconds": 1}),
-        ('1second', {"seconds": 1}),
-        ('1seconds', {"seconds": 1}),
-
-        # Complex duration strings
-        (
-            '1y1m1w1d1H1M1S',
-            {
-                "years": 1,
-                "months": 1,
-                "weeks": 1,
-                "days": 1,
-                "hours": 1,
-                "minutes": 1,
-                "seconds": 1
-            }
-        ),
-        ('5y100S', {"years": 5, "seconds": 100}),
-        ('2w28H', {"weeks": 2, "hours": 28}),
-
-        # Duration strings with spaces
-        ('1 year 2 months', {"years": 1, "months": 2}),
-        ('1d 2H', {"days": 1, "hours": 2}),
-        ('1 week2 days', {"weeks": 1, "days": 2}),
-    )
-)
-def create_future_datetime(request):
-    """Yields duration string and target datetime.datetime object."""
-    duration, duration_dict = request.param
-    future_datetime = FIXED_UTC_NOW + relativedelta(**duration_dict)
-    yield duration, future_datetime
-
-
-def test_duration_converter_for_valid(create_future_datetime: tuple):
-    converter = Duration()
-    duration, expected = create_future_datetime
-    with patch('bot.converters.datetime') as mock_datetime:
-        mock_datetime.utcnow.return_value = FIXED_UTC_NOW
-        assert asyncio.run(converter.convert(None, duration)) == expected
-
-
[email protected](
-    ('duration'),
-    (
-        # Units in wrong order
-        ('1d1w'),
-        ('1s1y'),
-
-        # Duplicated units
-        ('1 year 2 years'),
-        ('1 M 10 minutes'),
-
-        # Unknown substrings
-        ('1MVes'),
-        ('1y3breads'),
-
-        # Missing amount
-        ('ym'),
-
-        # Incorrect whitespace
-        (" 1y"),
-        ("1S "),
-        ("1y  1m"),
-
-        # Garbage
-        ('Guido van Rossum'),
-        ('lemon lemon lemon lemon lemon lemon lemon'),
-    )
-)
-def test_duration_converter_for_invalid(duration: str):
-    converter = Duration()
-    with pytest.raises(BadArgument, match=f'`{duration}` is not a valid duration string.'):
-        asyncio.run(converter.convert(None, duration))
-
-
[email protected](
-    ("datetime_string", "expected_dt"),
-    (
-
-        # `YYYY-mm-ddTHH:MM:SSZ` | `YYYY-mm-dd HH:MM:SSZ`
-        ('2019-09-02T02:03:05Z', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02 02:03:05Z', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-
-        # `YYYY-mm-ddTHH:MM:SS±HH:MM` | `YYYY-mm-dd HH:MM:SS±HH:MM`
-        ('2019-09-02T03:18:05+01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02 03:18:05+01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02T00:48:05-01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02 00:48:05-01:15', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-
-        # `YYYY-mm-ddTHH:MM:SS±HHMM` | `YYYY-mm-dd HH:MM:SS±HHMM`
-        ('2019-09-02T03:18:05+0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02 03:18:05+0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02T00:48:05-0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02 00:48:05-0115', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-
-        # `YYYY-mm-ddTHH:MM:SS±HH` | `YYYY-mm-dd HH:MM:SS±HH`
-        ('2019-09-02 03:03:05+01', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02T01:03:05-01', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-
-        # `YYYY-mm-ddTHH:MM:SS` | `YYYY-mm-dd HH:MM:SS`
-        ('2019-09-02T02:03:05', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-        ('2019-09-02 02:03:05', datetime.datetime(2019, 9, 2, 2, 3, 5)),
-
-        # `YYYY-mm-ddTHH:MM` | `YYYY-mm-dd HH:MM`
-        ('2019-11-12T09:15', datetime.datetime(2019, 11, 12, 9, 15)),
-        ('2019-11-12 09:15', datetime.datetime(2019, 11, 12, 9, 15)),
-
-        # `YYYY-mm-dd`
-        ('2019-04-01', datetime.datetime(2019, 4, 1)),
-
-        # `YYYY-mm`
-        ('2019-02-01', datetime.datetime(2019, 2, 1)),
-
-        # `YYYY`
-        ('2025', datetime.datetime(2025, 1, 1)),
-    ),
-)
-def test_isodatetime_converter_for_valid(datetime_string: str, expected_dt: datetime.datetime):
-    converter = ISODateTime()
-    converted_dt = asyncio.run(converter.convert(None, datetime_string))
-    assert converted_dt.tzinfo is None
-    assert converted_dt == expected_dt
-
-
[email protected](
-    ("datetime_string"),
-    (
-        # Make sure it doesn't interfere with the Duration converter
-        ('1Y'),
-        ('1d'),
-        ('1H'),
-
-        # Check if it fails when only providing the optional time part
-        ('10:10:10'),
-        ('10:00'),
-
-        # Invalid date format
-        ('19-01-01'),
-
-        # Other non-valid strings
-        ('fisk the tag master'),
-    ),
-)
-def test_isodatetime_converter_for_invalid(datetime_string: str):
-    converter = ISODateTime()
-    with pytest.raises(
-        BadArgument,
-        match=f"`{datetime_string}` is not a valid ISO-8601 datetime string",
-    ):
-        asyncio.run(converter.convert(None, datetime_string))
diff --git a/tests/test_helpers.py b/tests/test_helpers.py
new file mode 100644
index 000000000..7894e104a
--- /dev/null
+++ b/tests/test_helpers.py
@@ -0,0 +1,405 @@
+import asyncio
+import inspect
+import unittest
+import unittest.mock
+
+import discord
+
+from tests import helpers
+
+
+class DiscordMocksTests(unittest.TestCase):
+    """Tests for our specialized discord.py mocks."""
+
+    def test_mock_role_default_initialization(self):
+        """Test if the default initialization of MockRole results in the correct object."""
+        role = helpers.MockRole()
+
+        # The `spec` argument makes sure `isistance` checks with `discord.Role` pass
+        self.assertIsInstance(role, discord.Role)
+
+        self.assertEqual(role.name, "role")
+        self.assertEqual(role.position, 1)
+        self.assertEqual(role.mention, "&role")
+
+    def test_mock_role_alternative_arguments(self):
+        """Test if MockRole initializes with the arguments provided."""
+        role = helpers.MockRole(
+            name="Admins",
+            id=90210,
+            position=10,
+        )
+
+        self.assertEqual(role.name, "Admins")
+        self.assertEqual(role.id, 90210)
+        self.assertEqual(role.position, 10)
+        self.assertEqual(role.mention, "&Admins")
+
+    def test_mock_role_accepts_dynamic_arguments(self):
+        """Test if MockRole accepts and sets abitrary keyword arguments."""
+        role = helpers.MockRole(
+            guild="Dino Man",
+            hoist=True,
+        )
+
+        self.assertEqual(role.guild, "Dino Man")
+        self.assertTrue(role.hoist)
+
+    def test_mock_role_uses_position_for_less_than_greater_than(self):
+        """Test if `<` and `>` comparisons for MockRole are based on its position attribute."""
+        role_one = helpers.MockRole(position=1)
+        role_two = helpers.MockRole(position=2)
+        role_three = helpers.MockRole(position=3)
+
+        self.assertLess(role_one, role_two)
+        self.assertLess(role_one, role_three)
+        self.assertLess(role_two, role_three)
+        self.assertGreater(role_three, role_two)
+        self.assertGreater(role_three, role_one)
+        self.assertGreater(role_two, role_one)
+
+    def test_mock_member_default_initialization(self):
+        """Test if the default initialization of Mockmember results in the correct object."""
+        member = helpers.MockMember()
+
+        # The `spec` argument makes sure `isistance` checks with `discord.Member` pass
+        self.assertIsInstance(member, discord.Member)
+
+        self.assertEqual(member.name, "member")
+        self.assertListEqual(member.roles, [helpers.MockRole(name="@everyone", position=1, id=0)])
+        self.assertEqual(member.mention, "@member")
+
+    def test_mock_member_alternative_arguments(self):
+        """Test if MockMember initializes with the arguments provided."""
+        core_developer = helpers.MockRole(name="Core Developer", position=2)
+        member = helpers.MockMember(
+            name="Mark",
+            id=12345,
+            roles=[core_developer]
+        )
+
+        self.assertEqual(member.name, "Mark")
+        self.assertEqual(member.id, 12345)
+        self.assertListEqual(member.roles, [helpers.MockRole(name="@everyone", position=1, id=0), core_developer])
+        self.assertEqual(member.mention, "@Mark")
+
+    def test_mock_member_accepts_dynamic_arguments(self):
+        """Test if MockMember accepts and sets abitrary keyword arguments."""
+        member = helpers.MockMember(
+            nick="Dino Man",
+            colour=discord.Colour.default(),
+        )
+
+        self.assertEqual(member.nick, "Dino Man")
+        self.assertEqual(member.colour, discord.Colour.default())
+
+    def test_mock_guild_default_initialization(self):
+        """Test if the default initialization of Mockguild results in the correct object."""
+        guild = helpers.MockGuild()
+
+        # The `spec` argument makes sure `isistance` checks with `discord.Guild` pass
+        self.assertIsInstance(guild, discord.Guild)
+
+        self.assertListEqual(guild.roles, [helpers.MockRole(name="@everyone", position=1, id=0)])
+        self.assertListEqual(guild.members, [])
+
+    def test_mock_guild_alternative_arguments(self):
+        """Test if MockGuild initializes with the arguments provided."""
+        core_developer = helpers.MockRole(name="Core Developer", position=2)
+        guild = helpers.MockGuild(
+            roles=[core_developer],
+            members=[helpers.MockMember(id=54321)],
+        )
+
+        self.assertListEqual(guild.roles, [helpers.MockRole(name="@everyone", position=1, id=0), core_developer])
+        self.assertListEqual(guild.members, [helpers.MockMember(id=54321)])
+
+    def test_mock_guild_accepts_dynamic_arguments(self):
+        """Test if MockGuild accepts and sets abitrary keyword arguments."""
+        guild = helpers.MockGuild(
+            emojis=(":hyperjoseph:", ":pensive_ela:"),
+            premium_subscription_count=15,
+        )
+
+        self.assertTupleEqual(guild.emojis, (":hyperjoseph:", ":pensive_ela:"))
+        self.assertEqual(guild.premium_subscription_count, 15)
+
+    def test_mock_bot_default_initialization(self):
+        """Tests if MockBot initializes with the correct values."""
+        bot = helpers.MockBot()
+
+        # The `spec` argument makes sure `isistance` checks with `discord.ext.commands.Bot` pass
+        self.assertIsInstance(bot, discord.ext.commands.Bot)
+
+    def test_mock_context_default_initialization(self):
+        """Tests if MockContext initializes with the correct values."""
+        context = helpers.MockContext()
+
+        # The `spec` argument makes sure `isistance` checks with `discord.ext.commands.Context` pass
+        self.assertIsInstance(context, discord.ext.commands.Context)
+
+        self.assertIsInstance(context.bot, helpers.MockBot)
+        self.assertIsInstance(context.guild, helpers.MockGuild)
+        self.assertIsInstance(context.author, helpers.MockMember)
+
+    def test_mocks_allows_access_to_attributes_part_of_spec(self):
+        """Accessing attributes that are valid for the objects they mock should succeed."""
+        mocks = (
+            (helpers.MockGuild(), 'name'),
+            (helpers.MockRole(), 'hoist'),
+            (helpers.MockMember(), 'display_name'),
+            (helpers.MockBot(), 'user'),
+            (helpers.MockContext(), 'invoked_with'),
+            (helpers.MockTextChannel(), 'last_message'),
+            (helpers.MockMessage(), 'mention_everyone'),
+        )
+
+        for mock, valid_attribute in mocks:
+            with self.subTest(mock=mock):
+                try:
+                    getattr(mock, valid_attribute)
+                except AttributeError:
+                    msg = f"accessing valid attribute `{valid_attribute}` raised an AttributeError"
+                    self.fail(msg)
+
+    @unittest.mock.patch(f'{__name__}.DiscordMocksTests.subTest')
+    @unittest.mock.patch(f'{__name__}.getattr')
+    def test_mock_allows_access_to_attributes_test(self, mock_getattr, mock_subtest):
+        """The valid attribute test should raise an AssertionError after an AttributeError."""
+        mock_getattr.side_effect = AttributeError
+
+        msg = "accessing valid attribute `name` raised an AttributeError"
+        with self.assertRaises(AssertionError, msg=msg):
+            self.test_mocks_allows_access_to_attributes_part_of_spec()
+
+    def test_mocks_rejects_access_to_attributes_not_part_of_spec(self):
+        """Accessing attributes that are invalid for the objects they mock should fail."""
+        mocks = (
+            helpers.MockGuild(),
+            helpers.MockRole(),
+            helpers.MockMember(),
+            helpers.MockBot(),
+            helpers.MockContext(),
+            helpers.MockTextChannel(),
+            helpers.MockMessage(),
+        )
+
+        for mock in mocks:
+            with self.subTest(mock=mock):
+                with self.assertRaises(AttributeError):
+                    mock.the_cake_is_a_lie
+
+    def test_mocks_use_mention_when_provided_as_kwarg(self):
+        """The mock should use the passed `mention` instead of the default one if present."""
+        test_cases = (
+            (helpers.MockRole, "role mention"),
+            (helpers.MockMember, "member mention"),
+            (helpers.MockTextChannel, "channel mention"),
+        )
+
+        for mock_type, mention in test_cases:
+            with self.subTest(mock_type=mock_type, mention=mention):
+                mock = mock_type(mention=mention)
+                self.assertEqual(mock.mention, mention)
+
+    def test_create_test_on_mock_bot_closes_passed_coroutine(self):
+        """`bot.loop.create_task` should close the passed coroutine object to prevent warnings."""
+        async def dementati():
+            """Dummy coroutine for testing purposes."""
+
+        coroutine_object = dementati()
+
+        bot = helpers.MockBot()
+        bot.loop.create_task(coroutine_object)
+        with self.assertRaises(RuntimeError, msg="cannot reuse already awaited coroutine"):
+            asyncio.run(coroutine_object)
+
+
+class MockObjectTests(unittest.TestCase):
+    """Tests the mock objects and mixins we've defined."""
+
+    @classmethod
+    def setUpClass(cls):
+        cls.hashable_mocks = (helpers.MockRole, helpers.MockMember, helpers.MockGuild)
+
+    def test_colour_mixin(self):
+        """Test if the ColourMixin adds aliasing of color -> colour for child classes."""
+        class MockHemlock(unittest.mock.MagicMock, helpers.ColourMixin):
+            pass
+
+        hemlock = MockHemlock()
+        hemlock.color = 1
+        self.assertEqual(hemlock.colour, 1)
+        self.assertEqual(hemlock.colour, hemlock.color)
+
+    def test_hashable_mixin_hash_returns_id(self):
+        """Test if the HashableMixing uses the id attribute for hashing."""
+        class MockScragly(unittest.mock.Mock, helpers.HashableMixin):
+            pass
+
+        scragly = MockScragly()
+        scragly.id = 10
+        self.assertEqual(hash(scragly), scragly.id)
+
+    def test_hashable_mixin_uses_id_for_equality_comparison(self):
+        """Test if the HashableMixing uses the id attribute for hashing."""
+        class MockScragly(helpers.HashableMixin):
+            pass
+
+        scragly = MockScragly()
+        scragly.id = 10
+        eevee = MockScragly()
+        eevee.id = 10
+        python = MockScragly()
+        python.id = 20
+
+        self.assertTrue(scragly == eevee)
+        self.assertFalse(scragly == python)
+
+    def test_hashable_mixin_uses_id_for_nonequality_comparison(self):
+        """Test if the HashableMixing uses the id attribute for hashing."""
+        class MockScragly(helpers.HashableMixin):
+            pass
+
+        scragly = MockScragly()
+        scragly.id = 10
+        eevee = MockScragly()
+        eevee.id = 10
+        python = MockScragly()
+        python.id = 20
+
+        self.assertTrue(scragly != python)
+        self.assertFalse(scragly != eevee)
+
+    def test_mock_class_with_hashable_mixin_uses_id_for_hashing(self):
+        """Test if the MagicMock subclasses that implement the HashableMixin use id for hash."""
+        for mock in self.hashable_mocks:
+            with self.subTest(mock_class=mock):
+                instance = helpers.MockRole(id=100)
+                self.assertEqual(hash(instance), instance.id)
+
+    def test_mock_class_with_hashable_mixin_uses_id_for_equality(self):
+        """Test if MagicMocks that implement the HashableMixin use id for equality comparisons."""
+        for mock_class in self.hashable_mocks:
+            with self.subTest(mock_class=mock_class):
+                instance_one = mock_class()
+                instance_two = mock_class()
+                instance_three = mock_class()
+
+                instance_one.id = 10
+                instance_two.id = 10
+                instance_three.id = 20
+
+                self.assertTrue(instance_one == instance_two)
+                self.assertFalse(instance_one == instance_three)
+
+    def test_mock_class_with_hashable_mixin_uses_id_for_nonequality(self):
+        """Test if MagicMocks that implement HashableMixin use id for nonequality comparisons."""
+        for mock_class in self.hashable_mocks:
+            with self.subTest(mock_class=mock_class):
+                instance_one = mock_class()
+                instance_two = mock_class()
+                instance_three = mock_class()
+
+                instance_one.id = 10
+                instance_two.id = 10
+                instance_three.id = 20
+
+                self.assertFalse(instance_one != instance_two)
+                self.assertTrue(instance_one != instance_three)
+
+    def test_custom_mock_mixin_accepts_mock_seal(self):
+        """The `CustomMockMixin` should support `unittest.mock.seal`."""
+        class MyMock(helpers.CustomMockMixin, unittest.mock.MagicMock):
+
+            child_mock_type = unittest.mock.MagicMock
+            pass
+
+        mock = MyMock()
+        unittest.mock.seal(mock)
+        with self.assertRaises(AttributeError, msg="MyMock.shirayuki"):
+            mock.shirayuki = "hello!"
+
+    def test_spec_propagation_of_mock_subclasses(self):
+        """Test if the `spec` does not propagate to attributes of the mock object."""
+        test_values = (
+            (helpers.MockGuild, "region"),
+            (helpers.MockRole, "mentionable"),
+            (helpers.MockMember, "display_name"),
+            (helpers.MockBot, "owner_id"),
+            (helpers.MockContext, "command_failed"),
+            (helpers.MockMessage, "mention_everyone"),
+            (helpers.MockEmoji, 'managed'),
+            (helpers.MockPartialEmoji, 'url'),
+            (helpers.MockReaction, 'me'),
+        )
+
+        for mock_type, valid_attribute in test_values:
+            with self.subTest(mock_type=mock_type, attribute=valid_attribute):
+                mock = mock_type()
+                self.assertTrue(isinstance(mock, mock_type))
+                attribute = getattr(mock, valid_attribute)
+                self.assertTrue(isinstance(attribute, mock_type.child_mock_type))
+
+    def test_extract_coroutine_methods_from_spec_instance_should_extract_all_and_only_coroutines(self):
+        """Test if all coroutine functions are extracted, but not regular methods or attributes."""
+        class CoroutineDonor:
+            def __init__(self):
+                self.some_attribute = 'alpha'
+
+            async def first_coroutine():
+                """This coroutine function should be extracted."""
+
+            async def second_coroutine():
+                """This coroutine function should be extracted."""
+
+            def regular_method():
+                """This regular function should not be extracted."""
+
+        class Receiver:
+            pass
+
+        donor = CoroutineDonor()
+        receiver = Receiver()
+
+        helpers.CustomMockMixin._extract_coroutine_methods_from_spec_instance(receiver, donor)
+
+        self.assertIsInstance(receiver.first_coroutine, helpers.AsyncMock)
+        self.assertIsInstance(receiver.second_coroutine, helpers.AsyncMock)
+        self.assertFalse(hasattr(receiver, 'regular_method'))
+        self.assertFalse(hasattr(receiver, 'some_attribute'))
+
+    @unittest.mock.patch("builtins.super", new=unittest.mock.MagicMock())
+    @unittest.mock.patch("tests.helpers.CustomMockMixin._extract_coroutine_methods_from_spec_instance")
+    def test_custom_mock_mixin_init_with_spec(self, extract_method_mock):
+        """Test if CustomMockMixin correctly passes on spec/kwargs and calls the extraction method."""
+        spec_set = "pydis"
+
+        helpers.CustomMockMixin(spec_set=spec_set)
+
+        extract_method_mock.assert_called_once_with(spec_set)
+
+    @unittest.mock.patch("builtins.super", new=unittest.mock.MagicMock())
+    @unittest.mock.patch("tests.helpers.CustomMockMixin._extract_coroutine_methods_from_spec_instance")
+    def test_custom_mock_mixin_init_without_spec(self, extract_method_mock):
+        """Test if CustomMockMixin correctly passes on spec/kwargs and calls the extraction method."""
+        helpers.CustomMockMixin()
+
+        extract_method_mock.assert_not_called()
+
+    def test_async_mock_provides_coroutine_for_dunder_call(self):
+        """Test if AsyncMock objects have a coroutine for their __call__ method."""
+        async_mock = helpers.AsyncMock()
+        self.assertTrue(inspect.iscoroutinefunction(async_mock.__call__))
+
+        coroutine = async_mock()
+        self.assertTrue(inspect.iscoroutine(coroutine))
+        self.assertIsNotNone(asyncio.run(coroutine))
+
+    def test_async_test_decorator_allows_synchronous_call_to_async_def(self):
+        """Test if the `async_test` decorator allows an `async def` to be called synchronously."""
+        @helpers.async_test
+        async def kosayoda():
+            return "return value"
+
+        self.assertEqual(kosayoda(), "return value")
diff --git a/tests/test_resources.py b/tests/test_resources.py
deleted file mode 100644
index bcf124f05..000000000
--- a/tests/test_resources.py
+++ /dev/null
@@ -1,13 +0,0 @@
-import json
-from pathlib import Path
-
-
-def test_stars_valid():
-    """Validates that `bot/resources/stars.json` contains a list of strings."""
-
-    path = Path('bot', 'resources', 'stars.json')
-    content = path.read_text()
-    data = json.loads(content)
-
-    for name in data:
-        assert type(name) is str
diff --git a/tests/utils/test_checks.py b/tests/utils/test_checks.py
deleted file mode 100644
index 7121acebd..000000000
--- a/tests/utils/test_checks.py
+++ /dev/null
@@ -1,66 +0,0 @@
-from unittest.mock import MagicMock
-
-import pytest
-
-from bot.utils import checks
-
-
[email protected]()
-def context():
-    return MagicMock()
-
-
-def test_with_role_check_without_guild(context):
-    context.guild = None
-
-    assert not checks.with_role_check(context)
-
-
-def test_with_role_check_with_guild_without_required_role(context):
-    context.guild = True
-    context.author.roles = []
-
-    assert not checks.with_role_check(context)
-
-
-def test_with_role_check_with_guild_with_required_role(context):
-    context.guild = True
-    role = MagicMock()
-    role.id = 42
-    context.author.roles = (role,)
-
-    assert checks.with_role_check(context, role.id)
-
-
-def test_without_role_check_without_guild(context):
-    context.guild = None
-
-    assert not checks.without_role_check(context)
-
-
-def test_without_role_check_with_unwanted_role(context):
-    context.guild = True
-    role = MagicMock()
-    role.id = 42
-    context.author.roles = (role,)
-
-    assert not checks.without_role_check(context, role.id)
-
-
-def test_without_role_check_without_unwanted_role(context):
-    context.guild = True
-    role = MagicMock()
-    role.id = 42
-    context.author.roles = (role,)
-
-    assert checks.without_role_check(context, role.id + 10)
-
-
-def test_in_channel_check_for_correct_channel(context):
-    context.channel.id = 42
-    assert checks.in_channel_check(context, context.channel.id)
-
-
-def test_in_channel_check_for_incorrect_channel(context):
-    context.channel.id = 42
-    assert not checks.in_channel_check(context, context.channel.id + 10)