33 files changed, 652 insertions, 1019 deletions

diff --git a/tests/bot/cogs/test_duck_pond.py b/tests/bot/cogs/test_duck_pond.py
deleted file mode 100644
index cfe10aebf..000000000
--- a/tests/bot/cogs/test_duck_pond.py
+++ /dev/null
@@ -1,548 +0,0 @@
-import asyncio
-import logging
-import typing
-import unittest
-from unittest.mock import AsyncMock, 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.LoggingTestsMixin, unittest.IsolatedAsyncioTestCase):
-    """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_task.assert_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_guild_available.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_guild_available.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)
-
-    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 _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)
-
-    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)
-
-    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}.send_webhook"
-        send_attachments_path = f"{MODULE_PATH}.send_attachments"
-        author = MagicMock(
-            display_name="x",
-            avatar_url="https://"
-        )
-
-        self.cog.webhook = helpers.MockAsyncWebhook()
-
-        test_values = (
-            (helpers.MockMessage(author=author, clean_content="", attachments=[]), False, False),
-            (helpers.MockMessage(author=author, clean_content="message", attachments=[]), True, False),
-            (helpers.MockMessage(author=author, clean_content="", attachments=["attachment"]), False, True),
-            (helpers.MockMessage(author=author, 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=AsyncMock) as send_webhook:
-                with patch(send_attachments_path, new_callable=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=AsyncMock)
-    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:  # pragma: no cover
-            send_attachments.side_effect = side_effect
-            with patch(f"{MODULE_PATH}.send_webhook", new_callable=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}.send_webhook", new_callable=AsyncMock)
-    @patch(f"{MODULE_PATH}.send_attachments", new_callable=AsyncMock)
-    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(
-                webhook=self.cog.webhook,
-                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
-
-    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
-
-    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=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()
-
-    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=AsyncMock) as relay_message:
-                with patch(f"{MODULE_PATH}.DuckPond.count_ducks", new_callable=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)
-
-    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=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/__init__.py b/tests/bot/exts/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/bot/cogs/__init__.py
+++ b/tests/bot/exts/__init__.py
diff --git a/tests/bot/cogs/moderation/__init__.py b/tests/bot/exts/backend/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/bot/cogs/moderation/__init__.py
+++ b/tests/bot/exts/backend/__init__.py
diff --git a/tests/bot/cogs/sync/__init__.py b/tests/bot/exts/backend/sync/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/bot/cogs/sync/__init__.py
+++ b/tests/bot/exts/backend/sync/__init__.py
diff --git a/tests/bot/cogs/sync/test_base.py b/tests/bot/exts/backend/sync/test_base.py
index 70aea2bab..886c243cf 100644
--- a/tests/bot/cogs/sync/test_base.py
+++ b/tests/bot/exts/backend/sync/test_base.py
@@ -6,7 +6,7 @@ import discord
 
 from bot import constants
 from bot.api import ResponseCodeError
-from bot.cogs.sync.syncers import Syncer, _Diff
+from bot.exts.backend.sync._syncers import Syncer, _Diff
 from tests import helpers
 
 
diff --git a/tests/bot/cogs/sync/test_cog.py b/tests/bot/exts/backend/sync/test_cog.py
index 120bc991d..1b89564f2 100644
--- a/tests/bot/cogs/sync/test_cog.py
+++ b/tests/bot/exts/backend/sync/test_cog.py
@@ -5,8 +5,9 @@ import discord
 
 from bot import constants
 from bot.api import ResponseCodeError
-from bot.cogs import sync
-from bot.cogs.sync.syncers import Syncer
+from bot.exts.backend import sync
+from bot.exts.backend.sync._cog import Sync
+from bot.exts.backend.sync._syncers import Syncer
 from tests import helpers
 from tests.base import CommandTestCase
 
@@ -29,19 +30,19 @@ class SyncCogTestCase(unittest.IsolatedAsyncioTestCase):
         self.bot = helpers.MockBot()
 
         self.role_syncer_patcher = mock.patch(
-            "bot.cogs.sync.syncers.RoleSyncer",
+            "bot.exts.backend.sync._syncers.RoleSyncer",
             autospec=Syncer,
             spec_set=True
         )
         self.user_syncer_patcher = mock.patch(
-            "bot.cogs.sync.syncers.UserSyncer",
+            "bot.exts.backend.sync._syncers.UserSyncer",
             autospec=Syncer,
             spec_set=True
         )
         self.RoleSyncer = self.role_syncer_patcher.start()
         self.UserSyncer = self.user_syncer_patcher.start()
 
-        self.cog = sync.Sync(self.bot)
+        self.cog = Sync(self.bot)
 
     def tearDown(self):
         self.role_syncer_patcher.stop()
@@ -59,7 +60,7 @@ class SyncCogTestCase(unittest.IsolatedAsyncioTestCase):
 class SyncCogTests(SyncCogTestCase):
     """Tests for the Sync cog."""
 
-    @mock.patch.object(sync.Sync, "sync_guild", new_callable=mock.MagicMock)
+    @mock.patch.object(Sync, "sync_guild", new_callable=mock.MagicMock)
     def test_sync_cog_init(self, sync_guild):
         """Should instantiate syncers and run a sync for the guild."""
         # Reset because a Sync cog was already instantiated in setUp.
@@ -70,7 +71,7 @@ class SyncCogTests(SyncCogTestCase):
         mock_sync_guild_coro = mock.MagicMock()
         sync_guild.return_value = mock_sync_guild_coro
 
-        sync.Sync(self.bot)
+        Sync(self.bot)
 
         self.RoleSyncer.assert_called_once_with(self.bot)
         self.UserSyncer.assert_called_once_with(self.bot)
@@ -131,7 +132,7 @@ class SyncCogListenerTests(SyncCogTestCase):
         super().setUp()
         self.cog.patch_user = mock.AsyncMock(spec_set=self.cog.patch_user)
 
-        self.guild_id_patcher = mock.patch("bot.cogs.sync.cog.constants.Guild.id", 5)
+        self.guild_id_patcher = mock.patch("bot.exts.backend.sync._cog.constants.Guild.id", 5)
         self.guild_id = self.guild_id_patcher.start()
 
         self.guild = helpers.MockGuild(id=self.guild_id)
diff --git a/tests/bot/cogs/sync/test_roles.py b/tests/bot/exts/backend/sync/test_roles.py
index 79eee98f4..7b9f40cad 100644
--- a/tests/bot/cogs/sync/test_roles.py
+++ b/tests/bot/exts/backend/sync/test_roles.py
@@ -3,7 +3,7 @@ from unittest import mock
 
 import discord
 
-from bot.cogs.sync.syncers import RoleSyncer, _Diff, _Role
+from bot.exts.backend.sync._syncers import RoleSyncer, _Diff, _Role
 from tests import helpers
 
 
diff --git a/tests/bot/cogs/sync/test_users.py b/tests/bot/exts/backend/sync/test_users.py
index 002a947ad..c0a1da35c 100644
--- a/tests/bot/cogs/sync/test_users.py
+++ b/tests/bot/exts/backend/sync/test_users.py
@@ -1,7 +1,7 @@
 import unittest
 from unittest import mock
 
-from bot.cogs.sync.syncers import UserSyncer, _Diff, _User
+from bot.exts.backend.sync._syncers import UserSyncer, _Diff, _User
 from tests import helpers
 
 
diff --git a/tests/bot/cogs/test_logging.py b/tests/bot/exts/backend/test_logging.py
index 8a18fdcd6..466f207d9 100644
--- a/tests/bot/cogs/test_logging.py
+++ b/tests/bot/exts/backend/test_logging.py
@@ -2,7 +2,7 @@ import unittest
 from unittest.mock import patch
 
 from bot import constants
-from bot.cogs.logging import Logging
+from bot.exts.backend.logging import Logging
 from tests.helpers import MockBot, MockTextChannel
 
 
@@ -14,7 +14,7 @@ class LoggingTests(unittest.IsolatedAsyncioTestCase):
         self.cog = Logging(self.bot)
         self.dev_log = MockTextChannel(id=1234, name="dev-log")
 
-    @patch("bot.cogs.logging.DEBUG_MODE", False)
+    @patch("bot.exts.backend.logging.DEBUG_MODE", False)
     async def test_debug_mode_false(self):
         """Should send connected message to dev-log."""
         self.bot.get_channel.return_value = self.dev_log
@@ -24,7 +24,7 @@ class LoggingTests(unittest.IsolatedAsyncioTestCase):
         self.bot.get_channel.assert_called_once_with(constants.Channels.dev_log)
         self.dev_log.send.assert_awaited_once()
 
-    @patch("bot.cogs.logging.DEBUG_MODE", True)
+    @patch("bot.exts.backend.logging.DEBUG_MODE", True)
     async def test_debug_mode_true(self):
         """Should not send anything to dev-log."""
         await self.cog.startup_greeting()
diff --git a/tests/bot/exts/filters/__init__.py b/tests/bot/exts/filters/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/filters/__init__.py
diff --git a/tests/bot/cogs/test_antimalware.py b/tests/bot/exts/filters/test_antimalware.py
index ecb7abf00..3393c6cdc 100644
--- a/tests/bot/cogs/test_antimalware.py
+++ b/tests/bot/exts/filters/test_antimalware.py
@@ -3,8 +3,8 @@ from unittest.mock import AsyncMock, Mock
 
 from discord import NotFound
 
-from bot.cogs import antimalware
 from bot.constants import Channels, STAFF_ROLES
+from bot.exts.filters import antimalware
 from tests.helpers import MockAttachment, MockBot, MockMessage, MockRole
 
 
@@ -23,6 +23,8 @@ class AntiMalwareCogTests(unittest.IsolatedAsyncioTestCase):
         }
         self.cog = antimalware.AntiMalware(self.bot)
         self.message = MockMessage()
+        self.message.webhook_id = None
+        self.message.author.bot = None
         self.whitelist = [".first", ".second", ".third"]
 
     async def test_message_with_allowed_attachment(self):
@@ -48,6 +50,26 @@ class AntiMalwareCogTests(unittest.IsolatedAsyncioTestCase):
 
         self.message.delete.assert_not_called()
 
+    async def test_webhook_message_with_illegal_extension(self):
+        """A webhook message containing an illegal extension should be ignored."""
+        attachment = MockAttachment(filename="python.disallowed")
+        self.message.webhook_id = 697140105563078727
+        self.message.attachments = [attachment]
+
+        await self.cog.on_message(self.message)
+
+        self.message.delete.assert_not_called()
+
+    async def test_bot_message_with_illegal_extension(self):
+        """A bot message containing an illegal extension should be ignored."""
+        attachment = MockAttachment(filename="python.disallowed")
+        self.message.author.bot = 409107086526644234
+        self.message.attachments = [attachment]
+
+        await self.cog.on_message(self.message)
+
+        self.message.delete.assert_not_called()
+
     async def test_message_with_illegal_extension_gets_deleted(self):
         """A message containing an illegal extension should send an embed."""
         attachment = MockAttachment(filename="python.disallowed")
diff --git a/tests/bot/cogs/test_antispam.py b/tests/bot/exts/filters/test_antispam.py
index ce5472c71..6a0e4fded 100644
--- a/tests/bot/cogs/test_antispam.py
+++ b/tests/bot/exts/filters/test_antispam.py
@@ -1,6 +1,6 @@
 import unittest
 
-from bot.cogs import antispam
+from bot.exts.filters import antispam
 
 
 class AntispamConfigurationValidationTests(unittest.TestCase):
diff --git a/tests/bot/cogs/test_security.py b/tests/bot/exts/filters/test_security.py
index 9d1a62f7e..c0c3baa42 100644
--- a/tests/bot/cogs/test_security.py
+++ b/tests/bot/exts/filters/test_security.py
@@ -3,7 +3,7 @@ from unittest.mock import MagicMock
 
 from discord.ext.commands import NoPrivateMessage
 
-from bot.cogs import security
+from bot.exts.filters import security
 from tests.helpers import MockBot, MockContext
 
 
diff --git a/tests/bot/cogs/test_token_remover.py b/tests/bot/exts/filters/test_token_remover.py
index 5dee6922e..ea822053b 100644
--- a/tests/bot/cogs/test_token_remover.py
+++ b/tests/bot/exts/filters/test_token_remover.py
@@ -6,9 +6,9 @@ from unittest.mock import MagicMock
 from discord import Colour, NotFound
 
 from bot import constants
-from bot.cogs import token_remover
-from bot.cogs.moderation import ModLog
-from bot.cogs.token_remover import Token, TokenRemover
+from bot.exts.filters import token_remover
+from bot.exts.filters.token_remover import Token, TokenRemover
+from bot.exts.moderation.modlog import ModLog
 from bot.utils.messages import format_user
 from tests.helpers import MockBot, MockMessage, autospec
 
@@ -133,7 +133,7 @@ class TokenRemoverTests(unittest.IsolatedAsyncioTestCase):
             await cog.on_message(msg)
             find_token_in_message.assert_not_called()
 
-    @autospec("bot.cogs.token_remover", "TOKEN_RE")
+    @autospec("bot.exts.filters.token_remover", "TOKEN_RE")
     def test_find_token_no_matches(self, token_re):
         """None should be returned if the regex matches no tokens in a message."""
         token_re.finditer.return_value = ()
@@ -144,8 +144,8 @@ class TokenRemoverTests(unittest.IsolatedAsyncioTestCase):
         token_re.finditer.assert_called_once_with(self.msg.content)
 
     @autospec(TokenRemover, "is_valid_user_id", "is_valid_timestamp")
-    @autospec("bot.cogs.token_remover", "Token")
-    @autospec("bot.cogs.token_remover", "TOKEN_RE")
+    @autospec("bot.exts.filters.token_remover", "Token")
+    @autospec("bot.exts.filters.token_remover", "TOKEN_RE")
     def test_find_token_valid_match(self, token_re, token_cls, is_valid_id, is_valid_timestamp):
         """The first match with a valid user ID and timestamp should be returned as a `Token`."""
         matches = [
@@ -168,8 +168,8 @@ class TokenRemoverTests(unittest.IsolatedAsyncioTestCase):
         token_re.finditer.assert_called_once_with(self.msg.content)
 
     @autospec(TokenRemover, "is_valid_user_id", "is_valid_timestamp")
-    @autospec("bot.cogs.token_remover", "Token")
-    @autospec("bot.cogs.token_remover", "TOKEN_RE")
+    @autospec("bot.exts.filters.token_remover", "Token")
+    @autospec("bot.exts.filters.token_remover", "TOKEN_RE")
     def test_find_token_invalid_matches(self, token_re, token_cls, is_valid_id, is_valid_timestamp):
         """None should be returned if no matches have valid user IDs or timestamps."""
         token_re.finditer.return_value = [mock.create_autospec(Match, spec_set=True, instance=True)]
@@ -231,7 +231,7 @@ class TokenRemoverTests(unittest.IsolatedAsyncioTestCase):
         results = [match[0] for match in results]
         self.assertCountEqual((token_1, token_2), results)
 
-    @autospec("bot.cogs.token_remover", "LOG_MESSAGE")
+    @autospec("bot.exts.filters.token_remover", "LOG_MESSAGE")
     def test_format_log_message(self, log_message):
         """Should correctly format the log message with info from the message and token."""
         token = Token("NDY3MjIzMjMwNjUwNzc3NjQx", "XsySD_", "s45jqDV_Iisn-symw0yDRrk_jf4")
@@ -249,7 +249,7 @@ class TokenRemoverTests(unittest.IsolatedAsyncioTestCase):
         )
 
     @mock.patch.object(TokenRemover, "mod_log", new_callable=mock.PropertyMock)
-    @autospec("bot.cogs.token_remover", "log")
+    @autospec("bot.exts.filters.token_remover", "log")
     @autospec(TokenRemover, "format_log_message")
     async def test_take_action(self, format_log_message, logger, mod_log_property):
         """Should delete the message and send a mod log."""
@@ -299,7 +299,7 @@ class TokenRemoverTests(unittest.IsolatedAsyncioTestCase):
 class TokenRemoverExtensionTests(unittest.TestCase):
     """Tests for the token_remover extension."""
 
-    @autospec("bot.cogs.token_remover", "TokenRemover")
+    @autospec("bot.exts.filters.token_remover", "TokenRemover")
     def test_extension_setup(self, cog):
         """The TokenRemover cog should be added."""
         bot = MockBot()
diff --git a/tests/bot/exts/info/__init__.py b/tests/bot/exts/info/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/info/__init__.py
diff --git a/tests/bot/cogs/test_information.py b/tests/bot/exts/info/test_information.py
index 79c0e0ad3..ba8d5d608 100644
--- a/tests/bot/cogs/test_information.py
+++ b/tests/bot/exts/info/test_information.py
@@ -6,11 +6,11 @@ import unittest.mock
 import discord
 
 from bot import constants
-from bot.cogs import information
+from bot.exts.info import information
 from bot.utils.checks import InWhitelistCheckFailure
 from tests import helpers
 
-COG_PATH = "bot.cogs.information.Information"
+COG_PATH = "bot.exts.info.information.Information"
 
 
 class InformationCogTests(unittest.TestCase):
@@ -97,7 +97,7 @@ class InformationCogTests(unittest.TestCase):
         self.assertEqual(admin_embed.title, "Admins info")
         self.assertEqual(admin_embed.colour, discord.Colour.red())
 
-    @unittest.mock.patch('bot.cogs.information.time_since')
+    @unittest.mock.patch('bot.exts.info.information.time_since')
     def test_server_info_command(self, time_since_patch):
         time_since_patch.return_value = '2 days ago'
 
@@ -215,10 +215,10 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
             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)
+                expected_output = "\n".join(expected_lines)
                 actual_output = asyncio.run(method(self.member))
 
-                self.assertEqual(expected_output, actual_output)
+                self.assertEqual((default_header, 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."""
@@ -249,7 +249,7 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
             },
         )
 
-        header = ["**Infractions**"]
+        header = "Infractions"
 
         self._method_subtests(self.cog.basic_user_infraction_counts, test_values, header)
 
@@ -258,7 +258,7 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
         test_values = (
             {
                 "api response": [],
-                "expected_lines": ["This user has never received an infraction."],
+                "expected_lines": ["No infractions"],
             },
             # Shows non-hidden inactive infraction as expected
             {
@@ -304,7 +304,7 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
             },
         )
 
-        header = ["**Infractions**"]
+        header = "Infractions"
 
         self._method_subtests(self.cog.expanded_user_infraction_counts, test_values, header)
 
@@ -313,15 +313,15 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
         test_values = (
             {
                 "api response": [],
-                "expected_lines": ["This user has never been nominated."],
+                "expected_lines": ["No nominations"],
             },
             {
                 "api response": [{'active': True}],
-                "expected_lines": ["This user is **currently** nominated (1 nomination in total)."],
+                "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)."],
+                "expected_lines": ["This user is **currently** nominated", "(2 nominations in total)"],
             },
             {
                 "api response": [{'active': False}],
@@ -334,13 +334,13 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
 
         )
 
-        header = ["**Nominations**"]
+        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])
[email protected]("bot.exts.info.information.time_since", new=unittest.mock.MagicMock(return_value="1 year ago"))
[email protected]("bot.exts.info.information.constants.MODERATION_CHANNELS", new=[50])
 class UserEmbedTests(unittest.TestCase):
     """Tests for the creation of the `!user` embed."""
 
@@ -350,7 +350,10 @@ class UserEmbedTests(unittest.TestCase):
         self.bot.api_client.get = unittest.mock.AsyncMock()
         self.cog = information.Information(self.bot)
 
-    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=unittest.mock.AsyncMock(return_value=""))
+    @unittest.mock.patch(
+        f"{COG_PATH}.basic_user_infraction_counts",
+        new=unittest.mock.AsyncMock(return_value=("Infractions", "basic infractions"))
+    )
     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))
@@ -362,7 +365,10 @@ class UserEmbedTests(unittest.TestCase):
 
         self.assertEqual(embed.title, "Mr. Hemlock")
 
-    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=unittest.mock.AsyncMock(return_value=""))
+    @unittest.mock.patch(
+        f"{COG_PATH}.basic_user_infraction_counts",
+        new=unittest.mock.AsyncMock(return_value=("Infractions", "basic infractions"))
+    )
     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))
@@ -374,7 +380,10 @@ class UserEmbedTests(unittest.TestCase):
 
         self.assertEqual(embed.title, "Cat lover (Mr. Hemlock)")
 
-    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=unittest.mock.AsyncMock(return_value=""))
+    @unittest.mock.patch(
+        f"{COG_PATH}.basic_user_infraction_counts",
+        new=unittest.mock.AsyncMock(return_value=("Infractions", "basic infractions"))
+    )
     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))
@@ -386,8 +395,8 @@ class UserEmbedTests(unittest.TestCase):
 
         embed = asyncio.run(self.cog.create_user_embed(ctx, user))
 
-        self.assertIn("&Admins", embed.description)
-        self.assertNotIn("&Everyone", embed.description)
+        self.assertIn("&Admins", embed.fields[1].value)
+        self.assertNotIn("&Everyone", embed.fields[1].value)
 
     @unittest.mock.patch(f"{COG_PATH}.expanded_user_infraction_counts", new_callable=unittest.mock.AsyncMock)
     @unittest.mock.patch(f"{COG_PATH}.user_nomination_counts", new_callable=unittest.mock.AsyncMock)
@@ -398,8 +407,8 @@ class UserEmbedTests(unittest.TestCase):
         moderators_role = helpers.MockRole(name='Moderators')
         moderators_role.colour = 100
 
-        infraction_counts.return_value = "expanded infractions info"
-        nomination_counts.return_value = "nomination info"
+        infraction_counts.return_value = ("Infractions", "expanded infractions info")
+        nomination_counts.return_value = ("Nominations", "nomination info")
 
         user = helpers.MockMember(id=314, roles=[moderators_role], top_role=moderators_role)
         embed = asyncio.run(self.cog.create_user_embed(ctx, user))
@@ -409,20 +418,19 @@ class UserEmbedTests(unittest.TestCase):
 
         self.assertEqual(
             textwrap.dedent(f"""
-                **User Information**
                 Created: {"1 year ago"}
                 Profile: {user.mention}
                 ID: {user.id}
+            """).strip(),
+            embed.fields[0].value
+        )
 
-                **Member Information**
+        self.assertEqual(
+            textwrap.dedent(f"""
                 Joined: {"1 year ago"}
                 Roles: &Moderators
-
-                expanded infractions info
-
-                nomination info
             """).strip(),
-            embed.description
+            embed.fields[1].value
         )
 
     @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new_callable=unittest.mock.AsyncMock)
@@ -433,7 +441,7 @@ class UserEmbedTests(unittest.TestCase):
         moderators_role = helpers.MockRole(name='Moderators')
         moderators_role.colour = 100
 
-        infraction_counts.return_value = "basic infractions info"
+        infraction_counts.return_value = ("Infractions", "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))
@@ -442,21 +450,30 @@ class UserEmbedTests(unittest.TestCase):
 
         self.assertEqual(
             textwrap.dedent(f"""
-                **User Information**
                 Created: {"1 year ago"}
                 Profile: {user.mention}
                 ID: {user.id}
+            """).strip(),
+            embed.fields[0].value
+        )
 
-                **Member Information**
+        self.assertEqual(
+            textwrap.dedent(f"""
                 Joined: {"1 year ago"}
                 Roles: &Moderators
-
-                basic infractions info
             """).strip(),
-            embed.description
+            embed.fields[1].value
+        )
+
+        self.assertEqual(
+            "basic infractions info",
+            embed.fields[3].value
         )
 
-    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=unittest.mock.AsyncMock(return_value=""))
+    @unittest.mock.patch(
+        f"{COG_PATH}.basic_user_infraction_counts",
+        new=unittest.mock.AsyncMock(return_value=("Infractions", "basic infractions"))
+    )
     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()
@@ -469,7 +486,10 @@ class UserEmbedTests(unittest.TestCase):
 
         self.assertEqual(embed.colour, discord.Colour(moderators_role.colour))
 
-    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=unittest.mock.AsyncMock(return_value=""))
+    @unittest.mock.patch(
+        f"{COG_PATH}.basic_user_infraction_counts",
+        new=unittest.mock.AsyncMock(return_value=("Infractions", "basic infractions"))
+    )
     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()
@@ -479,7 +499,10 @@ class UserEmbedTests(unittest.TestCase):
 
         self.assertEqual(embed.colour, discord.Colour.blurple())
 
-    @unittest.mock.patch(f"{COG_PATH}.basic_user_infraction_counts", new=unittest.mock.AsyncMock(return_value=""))
+    @unittest.mock.patch(
+        f"{COG_PATH}.basic_user_infraction_counts",
+        new=unittest.mock.AsyncMock(return_value=("Infractions", "basic infractions"))
+    )
     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()
@@ -492,7 +515,7 @@ class UserEmbedTests(unittest.TestCase):
         self.assertEqual(embed.thumbnail.url, "avatar url")
 
 
[email protected]("bot.cogs.information.constants")
[email protected]("bot.exts.info.information.constants")
 class UserCommandTests(unittest.TestCase):
     """Tests for the `!user` command."""
 
@@ -531,7 +554,7 @@ class UserCommandTests(unittest.TestCase):
         with self.assertRaises(InWhitelistCheckFailure, msg=msg):
             asyncio.run(self.cog.user_info.callback(self.cog, ctx))
 
-    @unittest.mock.patch("bot.cogs.information.Information.create_user_embed", new_callable=unittest.mock.AsyncMock)
+    @unittest.mock.patch("bot.exts.info.information.Information.create_user_embed")
     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]
@@ -544,7 +567,7 @@ class UserCommandTests(unittest.TestCase):
         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=unittest.mock.AsyncMock)
+    @unittest.mock.patch("bot.exts.info.information.Information.create_user_embed")
     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]
@@ -557,7 +580,7 @@ class UserCommandTests(unittest.TestCase):
         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=unittest.mock.AsyncMock)
+    @unittest.mock.patch("bot.exts.info.information.Information.create_user_embed")
     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]
@@ -570,7 +593,7 @@ class UserCommandTests(unittest.TestCase):
         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=unittest.mock.AsyncMock)
+    @unittest.mock.patch("bot.exts.info.information.Information.create_user_embed")
     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]
diff --git a/tests/bot/exts/moderation/__init__.py b/tests/bot/exts/moderation/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/moderation/__init__.py
diff --git a/tests/bot/exts/moderation/infraction/__init__.py b/tests/bot/exts/moderation/infraction/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/moderation/infraction/__init__.py
diff --git a/tests/bot/cogs/moderation/test_infractions.py b/tests/bot/exts/moderation/infraction/test_infractions.py
index da4e92ccc..be1b649e1 100644
--- a/tests/bot/cogs/moderation/test_infractions.py
+++ b/tests/bot/exts/moderation/infraction/test_infractions.py
@@ -2,7 +2,7 @@ import textwrap
 import unittest
 from unittest.mock import AsyncMock, Mock, patch
 
-from bot.cogs.moderation.infractions import Infractions
+from bot.exts.moderation.infraction.infractions import Infractions
 from tests.helpers import MockBot, MockContext, MockGuild, MockMember, MockRole
 
 
@@ -17,8 +17,8 @@ class TruncationTests(unittest.IsolatedAsyncioTestCase):
         self.guild = MockGuild(id=4567)
         self.ctx = MockContext(bot=self.bot, author=self.user, guild=self.guild)
 
-    @patch("bot.cogs.moderation.utils.get_active_infraction")
-    @patch("bot.cogs.moderation.utils.post_infraction")
+    @patch("bot.exts.moderation.infraction._utils.get_active_infraction")
+    @patch("bot.exts.moderation.infraction._utils.post_infraction")
     async def test_apply_ban_reason_truncation(self, post_infraction_mock, get_active_mock):
         """Should truncate reason for `ctx.guild.ban`."""
         get_active_mock.return_value = None
@@ -39,7 +39,7 @@ class TruncationTests(unittest.IsolatedAsyncioTestCase):
             self.ctx, {"foo": "bar"}, self.target, self.ctx.guild.ban.return_value
         )
 
-    @patch("bot.cogs.moderation.utils.post_infraction")
+    @patch("bot.exts.moderation.infraction._utils.post_infraction")
     async def test_apply_kick_reason_truncation(self, post_infraction_mock):
         """Should truncate reason for `Member.kick`."""
         post_infraction_mock.return_value = {"foo": "bar"}
diff --git a/tests/bot/exts/moderation/infraction/test_utils.py b/tests/bot/exts/moderation/infraction/test_utils.py
new file mode 100644
index 000000000..5b62463e0
--- /dev/null
+++ b/tests/bot/exts/moderation/infraction/test_utils.py
@@ -0,0 +1,359 @@
+import unittest
+from collections import namedtuple
+from datetime import datetime
+from unittest.mock import AsyncMock, MagicMock, call, patch
+
+from discord import Embed, Forbidden, HTTPException, NotFound
+
+from bot.api import ResponseCodeError
+from bot.constants import Colours, Icons
+from bot.exts.moderation.infraction import _utils as utils
+from tests.helpers import MockBot, MockContext, MockMember, MockUser
+
+
+class ModerationUtilsTests(unittest.IsolatedAsyncioTestCase):
+    """Tests Moderation utils."""
+
+    def setUp(self):
+        self.bot = MockBot()
+        self.member = MockMember(id=1234)
+        self.user = MockUser(id=1234)
+        self.ctx = MockContext(bot=self.bot, author=self.member)
+
+    async def test_post_user(self):
+        """Should POST a new user and return the response if successful or otherwise send an error message."""
+        user = MockUser(discriminator=5678, id=1234, name="Test user")
+        not_user = MagicMock(discriminator=3333, id=5678, name="Wrong user")
+        test_cases = [
+            {
+                "user": user,
+                "post_result": "bar",
+                "raise_error": None,
+                "payload": {
+                    "discriminator": 5678,
+                    "id": self.user.id,
+                    "in_guild": False,
+                    "name": "Test user",
+                    "roles": []
+                }
+            },
+            {
+                "user": self.member,
+                "post_result": "foo",
+                "raise_error": ResponseCodeError(MagicMock(status=400), "foo"),
+                "payload": {
+                    "discriminator": 0,
+                    "id": self.member.id,
+                    "in_guild": False,
+                    "name": "Name unknown",
+                    "roles": []
+                }
+            },
+            {
+                "user": not_user,
+                "post_result": "bar",
+                "raise_error": None,
+                "payload": {
+                    "discriminator": not_user.discriminator,
+                    "id": not_user.id,
+                    "in_guild": False,
+                    "name": not_user.name,
+                    "roles": []
+                }
+            }
+        ]
+
+        for case in test_cases:
+            user = case["user"]
+            post_result = case["post_result"]
+            raise_error = case["raise_error"]
+            payload = case["payload"]
+
+            with self.subTest(user=user, post_result=post_result, raise_error=raise_error, payload=payload):
+                self.bot.api_client.post.reset_mock(side_effect=True)
+                self.ctx.bot.api_client.post.return_value = post_result
+
+                self.ctx.bot.api_client.post.side_effect = raise_error
+
+                result = await utils.post_user(self.ctx, user)
+
+                if raise_error:
+                    self.assertIsNone(result)
+                    self.ctx.send.assert_awaited_once()
+                    self.assertIn(str(raise_error.status), self.ctx.send.call_args[0][0])
+                else:
+                    self.assertEqual(result, post_result)
+                    self.bot.api_client.post.assert_awaited_once_with("bot/users", json=payload)
+
+    async def test_get_active_infraction(self):
+        """
+        Should request the API for active infractions and return infraction if the user has one or `None` otherwise.
+
+        A message should be sent to the context indicating a user already has an infraction, if that's the case.
+        """
+        test_case = namedtuple("test_case", ["get_return_value", "expected_output", "infraction_nr", "send_msg"])
+        test_cases = [
+            test_case([], None, None, True),
+            test_case([{"id": 123987}], {"id": 123987}, "123987", False),
+            test_case([{"id": 123987}], {"id": 123987}, "123987", True)
+        ]
+
+        for case in test_cases:
+            with self.subTest(return_value=case.get_return_value, expected=case.expected_output):
+                self.bot.api_client.get.reset_mock()
+                self.ctx.send.reset_mock()
+
+                params = {
+                    "active": "true",
+                    "type": "ban",
+                    "user__id": str(self.member.id)
+                }
+
+                self.bot.api_client.get.return_value = case.get_return_value
+
+                result = await utils.get_active_infraction(self.ctx, self.member, "ban", send_msg=case.send_msg)
+                self.assertEqual(result, case.expected_output)
+                self.bot.api_client.get.assert_awaited_once_with("bot/infractions", params=params)
+
+                if case.send_msg and case.get_return_value:
+                    self.ctx.send.assert_awaited_once()
+                    sent_message = self.ctx.send.call_args[0][0]
+                    self.assertIn(case.infraction_nr, sent_message)
+                    self.assertIn("ban", sent_message)
+                else:
+                    self.ctx.send.assert_not_awaited()
+
+    @patch("bot.exts.moderation.infraction._utils.send_private_embed")
+    async def test_notify_infraction(self, send_private_embed_mock):
+        """
+        Should send an embed of a certain format as a DM and return `True` if DM successful.
+
+        Appealable infractions should have the appeal message in the embed's footer.
+        """
+        test_cases = [
+            {
+                "args": (self.user, "ban", "2020-02-26 09:20 (23 hours and 59 minutes)"),
+                "expected_output": Embed(
+                    title=utils.INFRACTION_TITLE,
+                    description=utils.INFRACTION_DESCRIPTION_TEMPLATE.format(
+                        type="Ban",
+                        expires="2020-02-26 09:20 (23 hours and 59 minutes)",
+                        reason="No reason provided."
+                    ),
+                    colour=Colours.soft_red,
+                    url=utils.RULES_URL
+                ).set_author(
+                    name=utils.INFRACTION_AUTHOR_NAME,
+                    url=utils.RULES_URL,
+                    icon_url=Icons.token_removed
+                ).set_footer(text=utils.INFRACTION_APPEAL_FOOTER),
+                "send_result": True
+            },
+            {
+                "args": (self.user, "warning", None, "Test reason."),
+                "expected_output": Embed(
+                    title=utils.INFRACTION_TITLE,
+                    description=utils.INFRACTION_DESCRIPTION_TEMPLATE.format(
+                        type="Warning",
+                        expires="N/A",
+                        reason="Test reason."
+                    ),
+                    colour=Colours.soft_red,
+                    url=utils.RULES_URL
+                ).set_author(
+                    name=utils.INFRACTION_AUTHOR_NAME,
+                    url=utils.RULES_URL,
+                    icon_url=Icons.token_removed
+                ),
+                "send_result": False
+            },
+            {
+                "args": (self.user, "note", None, None, Icons.defcon_denied),
+                "expected_output": Embed(
+                    title=utils.INFRACTION_TITLE,
+                    description=utils.INFRACTION_DESCRIPTION_TEMPLATE.format(
+                        type="Note",
+                        expires="N/A",
+                        reason="No reason provided."
+                    ),
+                    colour=Colours.soft_red,
+                    url=utils.RULES_URL
+                ).set_author(
+                    name=utils.INFRACTION_AUTHOR_NAME,
+                    url=utils.RULES_URL,
+                    icon_url=Icons.defcon_denied
+                ),
+                "send_result": False
+            },
+            {
+                "args": (self.user, "mute", "2020-02-26 09:20 (23 hours and 59 minutes)", "Test", Icons.defcon_denied),
+                "expected_output": Embed(
+                    title=utils.INFRACTION_TITLE,
+                    description=utils.INFRACTION_DESCRIPTION_TEMPLATE.format(
+                        type="Mute",
+                        expires="2020-02-26 09:20 (23 hours and 59 minutes)",
+                        reason="Test"
+                    ),
+                    colour=Colours.soft_red,
+                    url=utils.RULES_URL
+                ).set_author(
+                    name=utils.INFRACTION_AUTHOR_NAME,
+                    url=utils.RULES_URL,
+                    icon_url=Icons.defcon_denied
+                ).set_footer(text=utils.INFRACTION_APPEAL_FOOTER),
+                "send_result": False
+            },
+            {
+                "args": (self.user, "mute", None, "foo bar" * 4000, Icons.defcon_denied),
+                "expected_output": Embed(
+                    title=utils.INFRACTION_TITLE,
+                    description=utils.INFRACTION_DESCRIPTION_TEMPLATE.format(
+                        type="Mute",
+                        expires="N/A",
+                        reason="foo bar" * 4000
+                    )[:2045] + "...",
+                    colour=Colours.soft_red,
+                    url=utils.RULES_URL
+                ).set_author(
+                    name=utils.INFRACTION_AUTHOR_NAME,
+                    url=utils.RULES_URL,
+                    icon_url=Icons.defcon_denied
+                ).set_footer(text=utils.INFRACTION_APPEAL_FOOTER),
+                "send_result": True
+            }
+        ]
+
+        for case in test_cases:
+            with self.subTest(args=case["args"], expected=case["expected_output"], send=case["send_result"]):
+                send_private_embed_mock.reset_mock()
+
+                send_private_embed_mock.return_value = case["send_result"]
+                result = await utils.notify_infraction(*case["args"])
+
+                self.assertEqual(case["send_result"], result)
+
+                embed = send_private_embed_mock.call_args[0][1]
+
+                self.assertEqual(embed.to_dict(), case["expected_output"].to_dict())
+
+                send_private_embed_mock.assert_awaited_once_with(case["args"][0], embed)
+
+    @patch("bot.exts.moderation.infraction._utils.send_private_embed")
+    async def test_notify_pardon(self, send_private_embed_mock):
+        """Should send an embed of a certain format as a DM and return `True` if DM successful."""
+        test_case = namedtuple("test_case", ["args", "icon", "send_result"])
+        test_cases = [
+            test_case((self.user, "Test title", "Example content"), Icons.user_verified, True),
+            test_case((self.user, "Test title", "Example content", Icons.user_update), Icons.user_update, False)
+        ]
+
+        for case in test_cases:
+            expected = Embed(
+                description="Example content",
+                colour=Colours.soft_green
+            ).set_author(
+                name="Test title",
+                icon_url=case.icon
+            )
+
+            with self.subTest(args=case.args, expected=expected):
+                send_private_embed_mock.reset_mock()
+
+                send_private_embed_mock.return_value = case.send_result
+
+                result = await utils.notify_pardon(*case.args)
+                self.assertEqual(case.send_result, result)
+
+                embed = send_private_embed_mock.call_args[0][1]
+                self.assertEqual(embed.to_dict(), expected.to_dict())
+
+                send_private_embed_mock.assert_awaited_once_with(case.args[0], embed)
+
+    async def test_send_private_embed(self):
+        """Should DM the user and return `True` on success or `False` on failure."""
+        embed = Embed(title="Test", description="Test val")
+
+        test_case = namedtuple("test_case", ["expected_output", "raised_exception"])
+        test_cases = [
+            test_case(True, None),
+            test_case(False, HTTPException(AsyncMock(), AsyncMock())),
+            test_case(False, Forbidden(AsyncMock(), AsyncMock())),
+            test_case(False, NotFound(AsyncMock(), AsyncMock()))
+        ]
+
+        for case in test_cases:
+            with self.subTest(expected=case.expected_output, raised=case.raised_exception):
+                self.user.send.reset_mock(side_effect=True)
+                self.user.send.side_effect = case.raised_exception
+
+                result = await utils.send_private_embed(self.user, embed)
+
+                self.assertEqual(result, case.expected_output)
+                self.user.send.assert_awaited_once_with(embed=embed)
+
+
+class TestPostInfraction(unittest.IsolatedAsyncioTestCase):
+    """Tests for the `post_infraction` function."""
+
+    def setUp(self):
+        self.bot = MockBot()
+        self.member = MockMember(id=1234)
+        self.user = MockUser(id=1234)
+        self.ctx = MockContext(bot=self.bot, author=self.member)
+
+    async def test_normal_post_infraction(self):
+        """Should return response from POST request if there are no errors."""
+        now = datetime.now()
+        payload = {
+            "actor": self.ctx.author.id,
+            "hidden": True,
+            "reason": "Test reason",
+            "type": "ban",
+            "user": self.member.id,
+            "active": False,
+            "expires_at": now.isoformat()
+        }
+
+        self.ctx.bot.api_client.post.return_value = "foo"
+        actual = await utils.post_infraction(self.ctx, self.member, "ban", "Test reason", now, True, False)
+
+        self.assertEqual(actual, "foo")
+        self.ctx.bot.api_client.post.assert_awaited_once_with("bot/infractions", json=payload)
+
+    async def test_unknown_error_post_infraction(self):
+        """Should send an error message to chat when a non-400 error occurs."""
+        self.ctx.bot.api_client.post.side_effect = ResponseCodeError(AsyncMock(), AsyncMock())
+        self.ctx.bot.api_client.post.side_effect.status = 500
+
+        actual = await utils.post_infraction(self.ctx, self.user, "ban", "Test reason")
+        self.assertIsNone(actual)
+
+        self.assertTrue("500" in self.ctx.send.call_args[0][0])
+
+    @patch("bot.exts.moderation.infraction._utils.post_user", return_value=None)
+    async def test_user_not_found_none_post_infraction(self, post_user_mock):
+        """Should abort and return `None` when a new user fails to be posted."""
+        self.bot.api_client.post.side_effect = ResponseCodeError(MagicMock(status=400), {"user": "foo"})
+
+        actual = await utils.post_infraction(self.ctx, self.user, "mute", "Test reason")
+        self.assertIsNone(actual)
+        post_user_mock.assert_awaited_once_with(self.ctx, self.user)
+
+    @patch("bot.exts.moderation.infraction._utils.post_user", return_value="bar")
+    async def test_first_fail_second_success_user_post_infraction(self, post_user_mock):
+        """Should post the user if they don't exist, POST infraction again, and return the response if successful."""
+        payload = {
+            "actor": self.ctx.author.id,
+            "hidden": False,
+            "reason": "Test reason",
+            "type": "mute",
+            "user": self.user.id,
+            "active": True
+        }
+
+        self.bot.api_client.post.side_effect = [ResponseCodeError(MagicMock(status=400), {"user": "foo"}), "foo"]
+
+        actual = await utils.post_infraction(self.ctx, self.user, "mute", "Test reason")
+        self.assertEqual(actual, "foo")
+        self.bot.api_client.post.assert_has_awaits([call("bot/infractions", json=payload)] * 2)
+        post_user_mock.assert_awaited_once_with(self.ctx, self.user)
diff --git a/tests/bot/cogs/moderation/test_incidents.py b/tests/bot/exts/moderation/test_incidents.py
index 435a1cd51..cbf7f7bcf 100644
--- a/tests/bot/cogs/moderation/test_incidents.py
+++ b/tests/bot/exts/moderation/test_incidents.py
@@ -8,8 +8,8 @@ from unittest.mock import AsyncMock, MagicMock, call, patch
 import aiohttp
 import discord
 
-from bot.cogs.moderation import Incidents, incidents
 from bot.constants import Colours
+from bot.exts.moderation import incidents
 from tests.helpers import (
     MockAsyncWebhook,
     MockAttachment,
@@ -130,7 +130,7 @@ class TestMakeEmbed(unittest.IsolatedAsyncioTestCase):
         incident = MockMessage(content="this is an incident", attachments=[attachment])
 
         # Patch `download_file` to return our `file`
-        with patch("bot.cogs.moderation.incidents.download_file", AsyncMock(return_value=file)):
+        with patch("bot.exts.moderation.incidents.download_file", AsyncMock(return_value=file)):
             embed, returned_file = await incidents.make_embed(incident, incidents.Signal.ACTIONED, MockMember())
 
         self.assertIs(file, returned_file)
@@ -142,7 +142,7 @@ class TestMakeEmbed(unittest.IsolatedAsyncioTestCase):
         incident = MockMessage(content="this is an incident", attachments=[attachment])
 
         # Patch `download_file` to return None as if the download failed
-        with patch("bot.cogs.moderation.incidents.download_file", AsyncMock(return_value=None)):
+        with patch("bot.exts.moderation.incidents.download_file", AsyncMock(return_value=None)):
             embed, returned_file = await incidents.make_embed(incident, incidents.Signal.ACTIONED, MockMember())
 
         self.assertIsNone(returned_file)
@@ -215,7 +215,7 @@ class TestOwnReactions(unittest.TestCase):
         self.assertSetEqual(incidents.own_reactions(message), {"A", "B"})
 
 
-@patch("bot.cogs.moderation.incidents.ALL_SIGNALS", {"A", "B"})
+@patch("bot.exts.moderation.incidents.ALL_SIGNALS", {"A", "B"})
 class TestHasSignals(unittest.TestCase):
     """
     Assertions for the `has_signals` function.
@@ -229,7 +229,7 @@ class TestHasSignals(unittest.TestCase):
         message = MockMessage()
         own_reactions = MagicMock(return_value={"A", "B"})
 
-        with patch("bot.cogs.moderation.incidents.own_reactions", own_reactions):
+        with patch("bot.exts.moderation.incidents.own_reactions", own_reactions):
             self.assertTrue(incidents.has_signals(message))
 
     def test_has_signals_false(self):
@@ -237,11 +237,11 @@ class TestHasSignals(unittest.TestCase):
         message = MockMessage()
         own_reactions = MagicMock(return_value={"A", "C"})
 
-        with patch("bot.cogs.moderation.incidents.own_reactions", own_reactions):
+        with patch("bot.exts.moderation.incidents.own_reactions", own_reactions):
             self.assertFalse(incidents.has_signals(message))
 
 
-@patch("bot.cogs.moderation.incidents.Signal", MockSignal)
+@patch("bot.exts.moderation.incidents.Signal", MockSignal)
 class TestAddSignals(unittest.IsolatedAsyncioTestCase):
     """
     Assertions for the `add_signals` coroutine.
@@ -255,19 +255,19 @@ class TestAddSignals(unittest.IsolatedAsyncioTestCase):
         """Prepare a mock incident message for tests to use."""
         self.incident = MockMessage()
 
-    @patch("bot.cogs.moderation.incidents.own_reactions", MagicMock(return_value=set()))
+    @patch("bot.exts.moderation.incidents.own_reactions", MagicMock(return_value=set()))
     async def test_add_signals_missing(self):
         """All emoji are added when none are present."""
         await incidents.add_signals(self.incident)
         self.incident.add_reaction.assert_has_calls([call("A"), call("B")])
 
-    @patch("bot.cogs.moderation.incidents.own_reactions", MagicMock(return_value={"A"}))
+    @patch("bot.exts.moderation.incidents.own_reactions", MagicMock(return_value={"A"}))
     async def test_add_signals_partial(self):
         """Only missing emoji are added when some are present."""
         await incidents.add_signals(self.incident)
         self.incident.add_reaction.assert_has_calls([call("B")])
 
-    @patch("bot.cogs.moderation.incidents.own_reactions", MagicMock(return_value={"A", "B"}))
+    @patch("bot.exts.moderation.incidents.own_reactions", MagicMock(return_value={"A", "B"}))
     async def test_add_signals_present(self):
         """No emoji are added when all are present."""
         await incidents.add_signals(self.incident)
@@ -290,7 +290,7 @@ class TestIncidents(unittest.IsolatedAsyncioTestCase):
         Note that this will not schedule `crawl_incidents` in the background, as everything
         is being mocked. The `crawl_task` attribute will end up being None.
         """
-        self.cog_instance = Incidents(MockBot())
+        self.cog_instance = incidents.Incidents(MockBot())
 
 
 @patch("asyncio.sleep", AsyncMock())  # Prevent the coro from sleeping to speed up the test
@@ -326,25 +326,25 @@ class TestCrawlIncidents(TestIncidents):
         await self.cog_instance.crawl_incidents()
         self.cog_instance.bot.wait_until_guild_available.assert_awaited()
 
-    @patch("bot.cogs.moderation.incidents.add_signals", AsyncMock())
-    @patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=False))  # Message doesn't qualify
-    @patch("bot.cogs.moderation.incidents.has_signals", MagicMock(return_value=False))
+    @patch("bot.exts.moderation.incidents.add_signals", AsyncMock())
+    @patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=False))  # Message doesn't qualify
+    @patch("bot.exts.moderation.incidents.has_signals", MagicMock(return_value=False))
     async def test_crawl_incidents_noop_if_is_not_incident(self):
         """Signals are not added for a non-incident message."""
         await self.cog_instance.crawl_incidents()
         incidents.add_signals.assert_not_awaited()
 
-    @patch("bot.cogs.moderation.incidents.add_signals", AsyncMock())
-    @patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=True))  # Message qualifies
-    @patch("bot.cogs.moderation.incidents.has_signals", MagicMock(return_value=True))  # But already has signals
+    @patch("bot.exts.moderation.incidents.add_signals", AsyncMock())
+    @patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=True))  # Message qualifies
+    @patch("bot.exts.moderation.incidents.has_signals", MagicMock(return_value=True))  # But already has signals
     async def test_crawl_incidents_noop_if_message_already_has_signals(self):
         """Signals are not added for messages which already have them."""
         await self.cog_instance.crawl_incidents()
         incidents.add_signals.assert_not_awaited()
 
-    @patch("bot.cogs.moderation.incidents.add_signals", AsyncMock())
-    @patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=True))  # Message qualifies
-    @patch("bot.cogs.moderation.incidents.has_signals", MagicMock(return_value=False))  # And doesn't have signals
+    @patch("bot.exts.moderation.incidents.add_signals", AsyncMock())
+    @patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=True))  # Message qualifies
+    @patch("bot.exts.moderation.incidents.has_signals", MagicMock(return_value=False))  # And doesn't have signals
     async def test_crawl_incidents_add_signals_called(self):
         """Message has signals added as it does not have them yet and qualifies as an incident."""
         await self.cog_instance.crawl_incidents()
@@ -384,7 +384,7 @@ class TestArchive(TestIncidents):
         )
         built_embed = MagicMock(discord.Embed, id=123)  # We patch `make_embed` to return this
 
-        with patch("bot.cogs.moderation.incidents.make_embed", AsyncMock(return_value=(built_embed, None))):
+        with patch("bot.exts.moderation.incidents.make_embed", AsyncMock(return_value=(built_embed, None))):
             archive_return = await self.cog_instance.archive(incident, MagicMock(value="A"), MockMember())
 
         # Now we check that the webhook was given the correct args, and that `archive` returned True
@@ -451,8 +451,8 @@ class TestMakeConfirmationTask(TestIncidents):
         self.assertFalse(created_check(payload=MagicMock(message_id=0)))
 
 
-@patch("bot.cogs.moderation.incidents.ALLOWED_ROLES", {1, 2})
-@patch("bot.cogs.moderation.incidents.Incidents.make_confirmation_task", AsyncMock())  # Generic awaitable
+@patch("bot.exts.moderation.incidents.ALLOWED_ROLES", {1, 2})
+@patch("bot.exts.moderation.incidents.Incidents.make_confirmation_task", AsyncMock())  # Generic awaitable
 class TestProcessEvent(TestIncidents):
     """Tests for the `Incidents.process_event` coroutine."""
 
@@ -479,7 +479,7 @@ class TestProcessEvent(TestIncidents):
 
     async def test_process_event_no_archive_on_investigating(self):
         """Message is not archived on `Signal.INVESTIGATING`."""
-        with patch("bot.cogs.moderation.incidents.Incidents.archive", AsyncMock()) as mocked_archive:
+        with patch("bot.exts.moderation.incidents.Incidents.archive", AsyncMock()) as mocked_archive:
             await self.cog_instance.process_event(
                 reaction=incidents.Signal.INVESTIGATING.value,
                 incident=MockMessage(),
@@ -497,7 +497,7 @@ class TestProcessEvent(TestIncidents):
         """
         incident = MockMessage()
 
-        with patch("bot.cogs.moderation.incidents.Incidents.archive", AsyncMock(return_value=False)):
+        with patch("bot.exts.moderation.incidents.Incidents.archive", AsyncMock(return_value=False)):
             await self.cog_instance.process_event(
                 reaction=incidents.Signal.ACTIONED.value,
                 incident=incident,
@@ -510,7 +510,7 @@ class TestProcessEvent(TestIncidents):
         """Task given by `Incidents.make_confirmation_task` is awaited before method exits."""
         mock_task = AsyncMock()
 
-        with patch("bot.cogs.moderation.incidents.Incidents.make_confirmation_task", mock_task):
+        with patch("bot.exts.moderation.incidents.Incidents.make_confirmation_task", mock_task):
             await self.cog_instance.process_event(
                 reaction=incidents.Signal.ACTIONED.value,
                 incident=MockMessage(),
@@ -530,7 +530,7 @@ class TestProcessEvent(TestIncidents):
         mock_task = AsyncMock(side_effect=asyncio.TimeoutError())
 
         try:
-            with patch("bot.cogs.moderation.incidents.Incidents.make_confirmation_task", mock_task):
+            with patch("bot.exts.moderation.incidents.Incidents.make_confirmation_task", mock_task):
                 await self.cog_instance.process_event(
                     reaction=incidents.Signal.ACTIONED.value,
                     incident=MockMessage(),
@@ -712,7 +712,7 @@ class TestOnRawReactionAdd(TestIncidents):
         self.cog_instance.process_event = AsyncMock()
         self.cog_instance.resolve_message = AsyncMock(return_value=MockMessage())
 
-        with patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=False)):
+        with patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=False)):
             await self.cog_instance.on_raw_reaction_add(self.payload)
 
         self.cog_instance.process_event.assert_not_called()
@@ -733,7 +733,7 @@ class TestOnRawReactionAdd(TestIncidents):
         self.cog_instance.process_event = AsyncMock()
         self.cog_instance.resolve_message = AsyncMock(return_value=incident)
 
-        with patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=True)):
+        with patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=True)):
             await self.cog_instance.on_raw_reaction_add(self.payload)
 
         self.cog_instance.process_event.assert_called_with(
@@ -751,20 +751,20 @@ class TestOnMessage(TestIncidents):
     function is tested in `TestIsIncident` - here we do not worry about it.
     """
 
-    @patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=True))
+    @patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=True))
     async def test_on_message_incident(self):
         """Messages qualifying as incidents are passed to `add_signals`."""
         incident = MockMessage()
 
-        with patch("bot.cogs.moderation.incidents.add_signals", AsyncMock()) as mock_add_signals:
+        with patch("bot.exts.moderation.incidents.add_signals", AsyncMock()) as mock_add_signals:
             await self.cog_instance.on_message(incident)
 
         mock_add_signals.assert_called_once_with(incident)
 
-    @patch("bot.cogs.moderation.incidents.is_incident", MagicMock(return_value=False))
+    @patch("bot.exts.moderation.incidents.is_incident", MagicMock(return_value=False))
     async def test_on_message_non_incident(self):
         """Messages not qualifying as incidents are ignored."""
-        with patch("bot.cogs.moderation.incidents.add_signals", AsyncMock()) as mock_add_signals:
+        with patch("bot.exts.moderation.incidents.add_signals", AsyncMock()) as mock_add_signals:
             await self.cog_instance.on_message(MockMessage())
 
         mock_add_signals.assert_not_called()
diff --git a/tests/bot/cogs/moderation/test_modlog.py b/tests/bot/exts/moderation/test_modlog.py
index f2809f40a..f8f142484 100644
--- a/tests/bot/cogs/moderation/test_modlog.py
+++ b/tests/bot/exts/moderation/test_modlog.py
@@ -2,7 +2,7 @@ import unittest
 
 import discord
 
-from bot.cogs.moderation.modlog import ModLog
+from bot.exts.moderation.modlog import ModLog
 from tests.helpers import MockBot, MockTextChannel
 
 
diff --git a/tests/bot/cogs/moderation/test_silence.py b/tests/bot/exts/moderation/test_silence.py
index ab3d0742a..e2d44c637 100644
--- a/tests/bot/cogs/moderation/test_silence.py
+++ b/tests/bot/exts/moderation/test_silence.py
@@ -4,8 +4,8 @@ from unittest.mock import MagicMock, Mock
 
 from discord import PermissionOverwrite
 
-from bot.cogs.moderation.silence import Silence, SilenceNotifier
 from bot.constants import Channels, Emojis, Guild, Roles
+from bot.exts.moderation.silence import Silence, SilenceNotifier
 from tests.helpers import MockBot, MockContext, MockTextChannel
 
 
@@ -99,7 +99,7 @@ class SilenceTests(unittest.IsolatedAsyncioTestCase):
         self.bot.get_channel.called_once_with(Channels.mod_alerts)
         self.bot.get_channel.called_once_with(Channels.mod_log)
 
-    @mock.patch("bot.cogs.moderation.silence.SilenceNotifier")
+    @mock.patch("bot.exts.moderation.silence.SilenceNotifier")
     async def test_instance_vars_got_notifier(self, notifier):
         """Notifier was started with channel."""
         mod_log = MockTextChannel()
@@ -238,7 +238,7 @@ class SilenceTests(unittest.IsolatedAsyncioTestCase):
         del mock_permissions_dict['send_messages']
         self.assertDictEqual(mock_permissions_dict, new_permissions)
 
-    @mock.patch("bot.cogs.moderation.silence.asyncio")
+    @mock.patch("bot.exts.moderation.silence.asyncio")
     @mock.patch.object(Silence, "_mod_alerts_channel", create=True)
     def test_cog_unload_starts_task(self, alert_channel, asyncio_mock):
         """Task for sending an alert was created with present `muted_channels`."""
@@ -247,15 +247,17 @@ class SilenceTests(unittest.IsolatedAsyncioTestCase):
             alert_channel.send.assert_called_once_with(f"<@&{Roles.moderators}> channels left silenced on cog unload: ")
             asyncio_mock.create_task.assert_called_once_with(alert_channel.send())
 
-    @mock.patch("bot.cogs.moderation.silence.asyncio")
+    @mock.patch("bot.exts.moderation.silence.asyncio")
     def test_cog_unload_skips_task_start(self, asyncio_mock):
         """No task created with no channels."""
         self.cog.cog_unload()
         asyncio_mock.create_task.assert_not_called()
 
-    @mock.patch("bot.cogs.moderation.silence.with_role_check")
-    @mock.patch("bot.cogs.moderation.silence.MODERATION_ROLES", new=(1, 2, 3))
-    def test_cog_check(self, role_check):
+    @mock.patch("discord.ext.commands.has_any_role")
+    @mock.patch("bot.exts.moderation.silence.MODERATION_ROLES", new=(1, 2, 3))
+    async def test_cog_check(self, role_check):
         """Role check is called with `MODERATION_ROLES`"""
-        self.cog.cog_check(self.ctx)
-        role_check.assert_called_once_with(self.ctx, *(1, 2, 3))
+        role_check.return_value.predicate = mock.AsyncMock()
+        await self.cog.cog_check(self.ctx)
+        role_check.assert_called_once_with(*(1, 2, 3))
+        role_check.return_value.predicate.assert_awaited_once_with(self.ctx)
diff --git a/tests/bot/cogs/test_slowmode.py b/tests/bot/exts/moderation/test_slowmode.py
index f442814c8..dad751e0d 100644
--- a/tests/bot/cogs/test_slowmode.py
+++ b/tests/bot/exts/moderation/test_slowmode.py
@@ -3,8 +3,8 @@ from unittest import mock
 
 from dateutil.relativedelta import relativedelta
 
-from bot.cogs.moderation.slowmode import Slowmode
 from bot.constants import Emojis
+from bot.exts.moderation.slowmode import Slowmode
 from tests.helpers import MockBot, MockContext, MockTextChannel
 
 
@@ -103,9 +103,11 @@ class SlowmodeTests(unittest.IsolatedAsyncioTestCase):
             f'{Emojis.check_mark} The slowmode delay for #meta has been reset to 0 seconds.'
         )
 
-    @mock.patch("bot.cogs.moderation.slowmode.with_role_check")
-    @mock.patch("bot.cogs.moderation.slowmode.MODERATION_ROLES", new=(1, 2, 3))
-    def test_cog_check(self, role_check):
+    @mock.patch("bot.exts.moderation.slowmode.has_any_role")
+    @mock.patch("bot.exts.moderation.slowmode.MODERATION_ROLES", new=(1, 2, 3))
+    async def test_cog_check(self, role_check):
         """Role check is called with `MODERATION_ROLES`"""
-        self.cog.cog_check(self.ctx)
-        role_check.assert_called_once_with(self.ctx, *(1, 2, 3))
+        role_check.return_value.predicate = mock.AsyncMock()
+        await self.cog.cog_check(self.ctx)
+        role_check.assert_called_once_with(*(1, 2, 3))
+        role_check.return_value.predicate.assert_awaited_once_with(self.ctx)
diff --git a/tests/bot/cogs/test_cogs.py b/tests/bot/exts/test_cogs.py
index fdda59a8f..f8e120262 100644
--- a/tests/bot/cogs/test_cogs.py
+++ b/tests/bot/exts/test_cogs.py
@@ -10,7 +10,7 @@ from unittest import mock
 
 from discord.ext import commands
 
-from bot import cogs
+from bot import exts
 
 
 class CommandNameTests(unittest.TestCase):
@@ -29,13 +29,14 @@ class CommandNameTests(unittest.TestCase):
 
     @staticmethod
     def walk_modules() -> t.Iterator[ModuleType]:
-        """Yield imported modules from the bot.cogs subpackage."""
+        """Yield imported modules from the bot.exts subpackage."""
         def on_error(name: str) -> t.NoReturn:
             raise ImportError(name=name)  # pragma: no cover
 
         # The mock prevents asyncio.get_event_loop() from being called.
         with mock.patch("discord.ext.tasks.loop"):
-            for module in pkgutil.walk_packages(cogs.__path__, "bot.cogs.", onerror=on_error):
+            prefix = f"{exts.__name__}."
+            for module in pkgutil.walk_packages(exts.__path__, prefix, onerror=on_error):
                 if not module.ispkg:
                     yield importlib.import_module(module.name)
 
@@ -53,6 +54,7 @@ class CommandNameTests(unittest.TestCase):
         """Return a list of all qualified names, including aliases, for the `command`."""
         names = [f"{command.full_parent_name} {alias}".strip() for alias in command.aliases]
         names.append(command.qualified_name)
+        names += getattr(command, "root_aliases", [])
 
         return names
 
diff --git a/tests/bot/exts/utils/__init__.py b/tests/bot/exts/utils/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/utils/__init__.py
diff --git a/tests/bot/cogs/test_jams.py b/tests/bot/exts/utils/test_jams.py
index b4ad8535f..45e7b5b51 100644
--- a/tests/bot/cogs/test_jams.py
+++ b/tests/bot/exts/utils/test_jams.py
@@ -3,8 +3,8 @@ from unittest.mock import AsyncMock, MagicMock, create_autospec
 
 from discord import CategoryChannel
 
-from bot.cogs import jams
 from bot.constants import Roles
+from bot.exts.utils import jams
 from tests.helpers import MockBot, MockContext, MockGuild, MockMember, MockRole, MockTextChannel
 
 
diff --git a/tests/bot/cogs/test_snekbox.py b/tests/bot/exts/utils/test_snekbox.py
index 343e37db9..40b2202aa 100644
--- a/tests/bot/cogs/test_snekbox.py
+++ b/tests/bot/exts/utils/test_snekbox.py
@@ -1,13 +1,12 @@
 import asyncio
-import logging
 import unittest
 from unittest.mock import AsyncMock, MagicMock, Mock, call, create_autospec, patch
 
 from discord.ext import commands
 
 from bot import constants
-from bot.cogs import snekbox
-from bot.cogs.snekbox import Snekbox
+from bot.exts.utils import snekbox
+from bot.exts.utils.snekbox import Snekbox
 from tests.helpers import MockBot, MockContext, MockMessage, MockReaction, MockUser
 
 
@@ -39,43 +38,14 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
         result = await self.cog.upload_output("-" * (snekbox.MAX_PASTE_LEN + 1))
         self.assertEqual(result, "too long to upload")
 
-    async def test_upload_output(self):
+    @patch("bot.exts.utils.snekbox.send_to_paste_service")
+    async def test_upload_output(self, mock_paste_util):
         """Upload the eval output to the URLs.paste_service.format(key="documents") endpoint."""
-        key = "MarkDiamond"
-        resp = MagicMock()
-        resp.json = AsyncMock(return_value={"key": key})
-
-        context_manager = MagicMock()
-        context_manager.__aenter__.return_value = resp
-        self.bot.http_session.post.return_value = context_manager
-
-        self.assertEqual(
-            await self.cog.upload_output("My awesome output"),
-            constants.URLs.paste_service.format(key=key)
-        )
-        self.bot.http_session.post.assert_called_with(
-            constants.URLs.paste_service.format(key="documents"),
-            data="My awesome output",
-            raise_for_status=True
+        await self.cog.upload_output("Test output.")
+        mock_paste_util.assert_called_once_with(
+            self.bot.http_session, "Test output.", extension="txt"
         )
 
-    async def test_upload_output_gracefully_fallback_if_exception_during_request(self):
-        """Output upload gracefully fallback if the upload fail."""
-        resp = MagicMock()
-        resp.json = AsyncMock(side_effect=Exception)
-
-        context_manager = MagicMock()
-        context_manager.__aenter__.return_value = resp
-        self.bot.http_session.post.return_value = context_manager
-
-        log = logging.getLogger("bot.cogs.snekbox")
-        with self.assertLogs(logger=log, level='ERROR'):
-            await self.cog.upload_output('My awesome output!')
-
-    async def test_upload_output_gracefully_fallback_if_no_key_in_response(self):
-        """Output upload gracefully fallback if there is no key entry in the response body."""
-        self.assertEqual((await self.cog.upload_output('My awesome output!')), None)
-
     def test_prepare_input(self):
         cases = (
             ('print("Hello world!")', 'print("Hello world!")', 'non-formatted'),
@@ -99,14 +69,14 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
                 actual = self.cog.get_results_message({'stdout': stdout, 'returncode': returncode})
                 self.assertEqual(actual, expected)
 
-    @patch('bot.cogs.snekbox.Signals', side_effect=ValueError)
+    @patch('bot.exts.utils.snekbox.Signals', side_effect=ValueError)
     def test_get_results_message_invalid_signal(self, mock_signals: Mock):
         self.assertEqual(
             self.cog.get_results_message({'stdout': '', 'returncode': 127}),
             ('Your eval job has completed with return code 127', '')
         )
 
-    @patch('bot.cogs.snekbox.Signals')
+    @patch('bot.exts.utils.snekbox.Signals')
     def test_get_results_message_valid_signal(self, mock_signals: Mock):
         mock_signals.return_value.name = 'SIGTEST'
         self.assertEqual(
@@ -147,12 +117,12 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
             ('<!@', ("<!@\u200B", None), r'Convert <!@ to <!@\u200B'),
             (
                 '\u202E\u202E\u202E',
-                ('Code block escape attempt detected; will not output result', None),
+                ('Code block escape attempt detected; will not output result', 'https://testificate.com/'),
                 'Detect RIGHT-TO-LEFT OVERRIDE'
             ),
             (
                 '\u200B\u200B\u200B',
-                ('Code block escape attempt detected; will not output result', None),
+                ('Code block escape attempt detected; will not output result', 'https://testificate.com/'),
                 'Detect ZERO WIDTH SPACE'
             ),
             ('long\nbeard', ('001 | long\n002 | beard', None), 'Two line output'),
@@ -296,7 +266,7 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
         self.cog.get_results_message.assert_called_once_with({'stdout': 'ERROR', 'returncode': 127})
         self.cog.format_output.assert_not_called()
 
-    @patch("bot.cogs.snekbox.partial")
+    @patch("bot.exts.utils.snekbox.partial")
     async def test_continue_eval_does_continue(self, partial_mock):
         """Test that the continue_eval function does continue if required conditions are met."""
         ctx = MockContext(message=MockMessage(add_reaction=AsyncMock(), clear_reactions=AsyncMock()))
diff --git a/tests/bot/test_pagination.py b/tests/bot/test_pagination.py
index ce880d457..630f2516d 100644
--- a/tests/bot/test_pagination.py
+++ b/tests/bot/test_pagination.py
@@ -44,18 +44,3 @@ class LinePaginatorTests(TestCase):
         self.paginator.add_line('x' * (self.paginator.scale_to_size + 1))
         # Note: item at index 1 is the truncated line, index 0 is prefix
         self.assertEqual(self.paginator._current_page[1], 'x' * self.paginator.scale_to_size)
-
-
-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)
-
-        assert self.paginator.images == [image]
diff --git a/tests/bot/utils/test_checks.py b/tests/bot/utils/test_checks.py
index de72e5748..883465e0b 100644
--- a/tests/bot/utils/test_checks.py
+++ b/tests/bot/utils/test_checks.py
@@ -1,48 +1,50 @@
 import unittest
 from unittest.mock import MagicMock
 
+from discord import DMChannel
+
 from bot.utils import checks
 from bot.utils.checks import InWhitelistCheckFailure
 from tests.helpers import MockContext, MockRole
 
 
-class ChecksTests(unittest.TestCase):
+class ChecksTests(unittest.IsolatedAsyncioTestCase):
     """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))
+    async def test_has_any_role_check_without_guild(self):
+        """`has_any_role_check` returns `False` for non-guild channels."""
+        self.ctx.channel = MagicMock(DMChannel)
+        self.assertFalse(await checks.has_any_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."""
+    async def test_has_any_role_check_without_required_roles(self):
+        """`has_any_role_check` returns `False` if `Context.author` lacks the required role."""
         self.ctx.author.roles = []
-        self.assertFalse(checks.with_role_check(self.ctx))
+        self.assertFalse(await checks.has_any_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."""
+    async def test_has_any_role_check_with_guild_and_required_role(self):
+        """`has_any_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))
+        self.assertTrue(await checks.has_any_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))
+    async def test_has_no_roles_check_without_guild(self):
+        """`has_no_roles_check` should return `False` when `Context.guild` is None."""
+        self.ctx.channel = MagicMock(DMChannel)
+        self.assertFalse(await checks.has_no_roles_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."""
+    async def test_has_no_roles_check_returns_false_with_unwanted_role(self):
+        """`has_no_roles_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))
+        self.assertFalse(await checks.has_no_roles_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."""
+    async def test_has_no_roles_check_returns_true_without_unwanted_role(self):
+        """`has_no_roles_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))
+        self.assertTrue(await checks.has_no_roles_check(self.ctx, role_id + 10))
 
     def test_in_whitelist_check_correct_channel(self):
         """`in_whitelist_check` returns `True` if `Context.channel.id` is in the channel list."""
diff --git a/tests/bot/utils/test_redis_cache.py b/tests/bot/utils/test_redis_cache.py
deleted file mode 100644
index a2f0fe55d..000000000
--- a/tests/bot/utils/test_redis_cache.py
+++ /dev/null
@@ -1,265 +0,0 @@
-import asyncio
-import unittest
-
-import fakeredis.aioredis
-
-from bot.utils import RedisCache
-from bot.utils.redis_cache import NoBotInstanceError, NoNamespaceError, NoParentInstanceError
-from tests import helpers
-
-
-class RedisCacheTests(unittest.IsolatedAsyncioTestCase):
-    """Tests the RedisCache class from utils.redis_dict.py."""
-
-    async def asyncSetUp(self):  # noqa: N802
-        """Sets up the objects that only have to be initialized once."""
-        self.bot = helpers.MockBot()
-        self.bot.redis_session = await fakeredis.aioredis.create_redis_pool()
-
-        # Okay, so this is necessary so that we can create a clean new
-        # class for every test method, and we want that because it will
-        # ensure we get a fresh loop, which is necessary for test_increment_lock
-        # to be able to pass.
-        class DummyCog:
-            """A dummy cog, for dummies."""
-
-            redis = RedisCache()
-
-            def __init__(self, bot: helpers.MockBot):
-                self.bot = bot
-
-        self.cog = DummyCog(self.bot)
-
-        await self.cog.redis.clear()
-
-    def test_class_attribute_namespace(self):
-        """Test that RedisDict creates a namespace automatically for class attributes."""
-        self.assertEqual(self.cog.redis._namespace, "DummyCog.redis")
-
-    async def test_class_attribute_required(self):
-        """Test that errors are raised when not assigned as a class attribute."""
-        bad_cache = RedisCache()
-        self.assertIs(bad_cache._namespace, None)
-
-        with self.assertRaises(RuntimeError):
-            await bad_cache.set("test", "me_up_deadman")
-
-    async def test_set_get_item(self):
-        """Test that users can set and get items from the RedisDict."""
-        test_cases = (
-            ('favorite_fruit', 'melon'),
-            ('favorite_number', 86),
-            ('favorite_fraction', 86.54),
-            ('favorite_boolean', False),
-            ('other_boolean', True),
-        )
-
-        # Test that we can get and set different types.
-        for test in test_cases:
-            await self.cog.redis.set(*test)
-            self.assertEqual(await self.cog.redis.get(test[0]), test[1])
-
-        # Test that .get allows a default value
-        self.assertEqual(await self.cog.redis.get('favorite_nothing', "bearclaw"), "bearclaw")
-
-    async def test_set_item_type(self):
-        """Test that .set rejects keys and values that are not permitted."""
-        fruits = ["lemon", "melon", "apple"]
-
-        with self.assertRaises(TypeError):
-            await self.cog.redis.set(fruits, "nice")
-
-        with self.assertRaises(TypeError):
-            await self.cog.redis.set(4.23, "nice")
-
-    async def test_delete_item(self):
-        """Test that .delete allows us to delete stuff from the RedisCache."""
-        # Add an item and verify that it gets added
-        await self.cog.redis.set("internet", "firetruck")
-        self.assertEqual(await self.cog.redis.get("internet"), "firetruck")
-
-        # Delete that item and verify that it gets deleted
-        await self.cog.redis.delete("internet")
-        self.assertIs(await self.cog.redis.get("internet"), None)
-
-    async def test_contains(self):
-        """Test that we can check membership with .contains."""
-        await self.cog.redis.set('favorite_country', "Burkina Faso")
-
-        self.assertIs(await self.cog.redis.contains('favorite_country'), True)
-        self.assertIs(await self.cog.redis.contains('favorite_dentist'), False)
-
-    async def test_items(self):
-        """Test that the RedisDict can be iterated."""
-        # Set up our test cases in the Redis cache
-        test_cases = [
-            ('favorite_turtle', 'Donatello'),
-            ('second_favorite_turtle', 'Leonardo'),
-            ('third_favorite_turtle', 'Raphael'),
-        ]
-        for key, value in test_cases:
-            await self.cog.redis.set(key, value)
-
-        # Consume the AsyncIterator into a regular list, easier to compare that way.
-        redis_items = [item for item in await self.cog.redis.items()]
-
-        # These sequences are probably in the same order now, but probably
-        # isn't good enough for tests. Let's not rely on .hgetall always
-        # returning things in sequence, and just sort both lists to be safe.
-        redis_items = sorted(redis_items)
-        test_cases = sorted(test_cases)
-
-        # If these are equal now, everything works fine.
-        self.assertSequenceEqual(test_cases, redis_items)
-
-    async def test_length(self):
-        """Test that we can get the correct .length from the RedisDict."""
-        await self.cog.redis.set('one', 1)
-        await self.cog.redis.set('two', 2)
-        await self.cog.redis.set('three', 3)
-        self.assertEqual(await self.cog.redis.length(), 3)
-
-        await self.cog.redis.set('four', 4)
-        self.assertEqual(await self.cog.redis.length(), 4)
-
-    async def test_to_dict(self):
-        """Test that the .to_dict method returns a workable dictionary copy."""
-        copy = await self.cog.redis.to_dict()
-        local_copy = {key: value for key, value in await self.cog.redis.items()}
-        self.assertIs(type(copy), dict)
-        self.assertDictEqual(copy, local_copy)
-
-    async def test_clear(self):
-        """Test that the .clear method removes the entire hash."""
-        await self.cog.redis.set('teddy', 'with me')
-        await self.cog.redis.set('in my dreams', 'you have a weird hat')
-        self.assertEqual(await self.cog.redis.length(), 2)
-
-        await self.cog.redis.clear()
-        self.assertEqual(await self.cog.redis.length(), 0)
-
-    async def test_pop(self):
-        """Test that we can .pop an item from the RedisDict."""
-        await self.cog.redis.set('john', 'was afraid')
-
-        self.assertEqual(await self.cog.redis.pop('john'), 'was afraid')
-        self.assertEqual(await self.cog.redis.pop('pete', 'breakneck'), 'breakneck')
-        self.assertEqual(await self.cog.redis.length(), 0)
-
-    async def test_update(self):
-        """Test that we can .update the RedisDict with multiple items."""
-        await self.cog.redis.set("reckfried", "lona")
-        await self.cog.redis.set("bel air", "prince")
-        await self.cog.redis.update({
-            "reckfried": "jona",
-            "mega": "hungry, though",
-        })
-
-        result = {
-            "reckfried": "jona",
-            "bel air": "prince",
-            "mega": "hungry, though",
-        }
-        self.assertDictEqual(await self.cog.redis.to_dict(), result)
-
-    def test_typestring_conversion(self):
-        """Test the typestring-related helper functions."""
-        conversion_tests = (
-            (12, "i|12"),
-            (12.4, "f|12.4"),
-            ("cowabunga", "s|cowabunga"),
-        )
-
-        # Test conversion to typestring
-        for _input, expected in conversion_tests:
-            self.assertEqual(self.cog.redis._value_to_typestring(_input), expected)
-
-        # Test conversion from typestrings
-        for _input, expected in conversion_tests:
-            self.assertEqual(self.cog.redis._value_from_typestring(expected), _input)
-
-        # Test that exceptions are raised on invalid input
-        with self.assertRaises(TypeError):
-            self.cog.redis._value_to_typestring(["internet"])
-            self.cog.redis._value_from_typestring("o|firedog")
-
-    async def test_increment_decrement(self):
-        """Test .increment and .decrement methods."""
-        await self.cog.redis.set("entropic", 5)
-        await self.cog.redis.set("disentropic", 12.5)
-
-        # Test default increment
-        await self.cog.redis.increment("entropic")
-        self.assertEqual(await self.cog.redis.get("entropic"), 6)
-
-        # Test default decrement
-        await self.cog.redis.decrement("entropic")
-        self.assertEqual(await self.cog.redis.get("entropic"), 5)
-
-        # Test float increment with float
-        await self.cog.redis.increment("disentropic", 2.0)
-        self.assertEqual(await self.cog.redis.get("disentropic"), 14.5)
-
-        # Test float increment with int
-        await self.cog.redis.increment("disentropic", 2)
-        self.assertEqual(await self.cog.redis.get("disentropic"), 16.5)
-
-        # Test negative increments, because why not.
-        await self.cog.redis.increment("entropic", -5)
-        self.assertEqual(await self.cog.redis.get("entropic"), 0)
-
-        # Negative decrements? Sure.
-        await self.cog.redis.decrement("entropic", -5)
-        self.assertEqual(await self.cog.redis.get("entropic"), 5)
-
-        # What about if we use a negative float to decrement an int?
-        # This should convert the type into a float.
-        await self.cog.redis.decrement("entropic", -2.5)
-        self.assertEqual(await self.cog.redis.get("entropic"), 7.5)
-
-        # Let's test that they raise the right errors
-        with self.assertRaises(KeyError):
-            await self.cog.redis.increment("doesn't_exist!")
-
-        await self.cog.redis.set("stringthing", "stringthing")
-        with self.assertRaises(TypeError):
-            await self.cog.redis.increment("stringthing")
-
-    async def test_increment_lock(self):
-        """Test that we can't produce a race condition in .increment."""
-        await self.cog.redis.set("test_key", 0)
-        tasks = []
-
-        # Increment this a lot in different tasks
-        for _ in range(100):
-            task = asyncio.create_task(
-                self.cog.redis.increment("test_key", 1)
-            )
-            tasks.append(task)
-        await asyncio.gather(*tasks)
-
-        # Confirm that the value has been incremented the exact right number of times.
-        value = await self.cog.redis.get("test_key")
-        self.assertEqual(value, 100)
-
-    async def test_exceptions_raised(self):
-        """Testing that the various RuntimeErrors are reachable."""
-        class MyCog:
-            cache = RedisCache()
-
-            def __init__(self):
-                self.other_cache = RedisCache()
-
-        cog = MyCog()
-
-        # Raises "No Bot instance"
-        with self.assertRaises(NoBotInstanceError):
-            await cog.cache.get("john")
-
-        # Raises "RedisCache has no namespace"
-        with self.assertRaises(NoNamespaceError):
-            await cog.other_cache.get("was")
-
-        # Raises "You must access the RedisCache instance through the cog instance"
-        with self.assertRaises(NoParentInstanceError):
-            await MyCog.cache.get("afraid")
diff --git a/tests/bot/utils/test_services.py b/tests/bot/utils/test_services.py
new file mode 100644
index 000000000..5e0855704
--- /dev/null
+++ b/tests/bot/utils/test_services.py
@@ -0,0 +1,74 @@
+import logging
+import unittest
+from unittest.mock import AsyncMock, MagicMock, Mock, patch
+
+from aiohttp import ClientConnectorError
+
+from bot.utils.services import FAILED_REQUEST_ATTEMPTS, send_to_paste_service
+
+
+class PasteTests(unittest.IsolatedAsyncioTestCase):
+    def setUp(self) -> None:
+        self.http_session = MagicMock()
+
+    @patch("bot.utils.services.URLs.paste_service", "https://paste_service.com/{key}")
+    async def test_url_and_sent_contents(self):
+        """Correct url was used and post was called with expected data."""
+        response = MagicMock(
+            json=AsyncMock(return_value={"key": ""})
+        )
+        self.http_session.post().__aenter__.return_value = response
+        self.http_session.post.reset_mock()
+        await send_to_paste_service(self.http_session, "Content")
+        self.http_session.post.assert_called_once_with("https://paste_service.com/documents", data="Content")
+
+    @patch("bot.utils.services.URLs.paste_service", "https://paste_service.com/{key}")
+    async def test_paste_returns_correct_url_on_success(self):
+        """Url with specified extension is returned on successful requests."""
+        key = "paste_key"
+        test_cases = (
+            (f"https://paste_service.com/{key}.txt", "txt"),
+            (f"https://paste_service.com/{key}.py", "py"),
+            (f"https://paste_service.com/{key}", ""),
+        )
+        response = MagicMock(
+            json=AsyncMock(return_value={"key": key})
+        )
+        self.http_session.post().__aenter__.return_value = response
+
+        for expected_output, extension in test_cases:
+            with self.subTest(msg=f"Send contents with extension {repr(extension)}"):
+                self.assertEqual(
+                    await send_to_paste_service(self.http_session, "", extension=extension),
+                    expected_output
+                )
+
+    async def test_request_repeated_on_json_errors(self):
+        """Json with error message and invalid json are handled as errors and requests repeated."""
+        test_cases = ({"message": "error"}, {"unexpected_key": None}, {})
+        self.http_session.post().__aenter__.return_value = response = MagicMock()
+        self.http_session.post.reset_mock()
+
+        for error_json in test_cases:
+            with self.subTest(error_json=error_json):
+                response.json = AsyncMock(return_value=error_json)
+                result = await send_to_paste_service(self.http_session, "")
+                self.assertEqual(self.http_session.post.call_count, FAILED_REQUEST_ATTEMPTS)
+                self.assertIsNone(result)
+
+            self.http_session.post.reset_mock()
+
+    async def test_request_repeated_on_connection_errors(self):
+        """Requests are repeated in the case of connection errors."""
+        self.http_session.post = MagicMock(side_effect=ClientConnectorError(Mock(), Mock()))
+        result = await send_to_paste_service(self.http_session, "")
+        self.assertEqual(self.http_session.post.call_count, FAILED_REQUEST_ATTEMPTS)
+        self.assertIsNone(result)
+
+    async def test_general_error_handled_and_request_repeated(self):
+        """All `Exception`s are handled, logged and request repeated."""
+        self.http_session.post = MagicMock(side_effect=Exception)
+        result = await send_to_paste_service(self.http_session, "")
+        self.assertEqual(self.http_session.post.call_count, FAILED_REQUEST_ATTEMPTS)
+        self.assertLogs("bot.utils", logging.ERROR)
+        self.assertIsNone(result)
diff --git a/tests/helpers.py b/tests/helpers.py
index facc4e1af..e47fdf28f 100644
--- a/tests/helpers.py
+++ b/tests/helpers.py
@@ -308,7 +308,11 @@ class MockBot(CustomMockMixin, unittest.mock.MagicMock):
     Instances of this class will follow the specifications of `discord.ext.commands.Bot` instances.
     For more information, see the `MockGuild` docstring.
     """
-    spec_set = Bot(command_prefix=unittest.mock.MagicMock(), loop=_get_mock_loop())
+    spec_set = Bot(
+        command_prefix=unittest.mock.MagicMock(),
+        loop=_get_mock_loop(),
+        redis_session=unittest.mock.MagicMock(),
+    )
     additional_spec_asyncs = ("wait_for", "redis_ready")
 
     def __init__(self, **kwargs) -> None: