Merge branch 'master' into sebastiaan/bugs/duckpond

97 files changed, 901 insertions, 506 deletions

diff --git a/bot/__main__.py b/bot/__main__.py
index fe2cf90e6..8770ac31b 100644
--- a/bot/__main__.py
+++ b/bot/__main__.py
@@ -9,7 +9,9 @@ from sentry_sdk.integrations.redis import RedisIntegration
 
 from bot import constants, patches
 from bot.bot import Bot
+from bot.utils.extensions import EXTENSIONS
 
+# Set up Sentry.
 sentry_logging = LoggingIntegration(
     level=logging.DEBUG,
     event_level=logging.WARNING
@@ -24,6 +26,7 @@ sentry_sdk.init(
     ]
 )
 
+# Instantiate the bot.
 allowed_roles = [discord.Object(id_) for id_ in constants.MODERATION_ROLES]
 bot = Bot(
     command_prefix=when_mentioned_or(constants.Bot.prefix),
@@ -33,50 +36,13 @@ bot = Bot(
     allowed_mentions=discord.AllowedMentions(everyone=False, roles=allowed_roles)
 )
 
-# Internal/debug
-bot.load_extension("bot.cogs.config_verifier")
-bot.load_extension("bot.cogs.error_handler")
-bot.load_extension("bot.cogs.filtering")
-bot.load_extension("bot.cogs.logging")
-bot.load_extension("bot.cogs.security")
+# Load extensions.
+extensions = set(EXTENSIONS)  # Create a mutable copy.
+if not constants.HelpChannels.enable:
+    extensions.remove("bot.exts.help_channels")
 
-# Commands, etc
-bot.load_extension("bot.cogs.antimalware")
-bot.load_extension("bot.cogs.antispam")
-bot.load_extension("bot.cogs.bot")
-bot.load_extension("bot.cogs.clean")
-bot.load_extension("bot.cogs.doc")
-bot.load_extension("bot.cogs.extensions")
-bot.load_extension("bot.cogs.help")
-bot.load_extension("bot.cogs.verification")
-
-# Feature cogs
-bot.load_extension("bot.cogs.alias")
-bot.load_extension("bot.cogs.defcon")
-bot.load_extension("bot.cogs.dm_relay")
-bot.load_extension("bot.cogs.duck_pond")
-bot.load_extension("bot.cogs.eval")
-bot.load_extension("bot.cogs.filter_lists")
-bot.load_extension("bot.cogs.information")
-bot.load_extension("bot.cogs.jams")
-bot.load_extension("bot.cogs.moderation")
-bot.load_extension("bot.cogs.off_topic_names")
-bot.load_extension("bot.cogs.python_news")
-bot.load_extension("bot.cogs.reddit")
-bot.load_extension("bot.cogs.reminders")
-bot.load_extension("bot.cogs.site")
-bot.load_extension("bot.cogs.snekbox")
-bot.load_extension("bot.cogs.source")
-bot.load_extension("bot.cogs.stats")
-bot.load_extension("bot.cogs.sync")
-bot.load_extension("bot.cogs.tags")
-bot.load_extension("bot.cogs.token_remover")
-bot.load_extension("bot.cogs.utils")
-bot.load_extension("bot.cogs.watchchannels")
-bot.load_extension("bot.cogs.webhook_remover")
-
-if constants.HelpChannels.enable:
-    bot.load_extension("bot.cogs.help_channels")
+for extension in extensions:
+    bot.load_extension(extension)
 
 # Apply `message_edited_at` patch if discord.py did not yet release a bug fix.
 if not hasattr(discord.message.Message, '_handle_edited_timestamp'):
diff --git a/bot/cogs/moderation/__init__.py b/bot/cogs/moderation/__init__.py
deleted file mode 100644
index 995187ef0..000000000
--- a/bot/cogs/moderation/__init__.py
+++ /dev/null
@@ -1,19 +0,0 @@
-from bot.bot import Bot
-from .incidents import Incidents
-from .infractions import Infractions
-from .management import ModManagement
-from .modlog import ModLog
-from .silence import Silence
-from .slowmode import Slowmode
-from .superstarify import Superstarify
-
-
-def setup(bot: Bot) -> None:
-    """Load the Incidents, Infractions, ModManagement, ModLog, Silence, Slowmode and Superstarify cogs."""
-    bot.add_cog(Incidents(bot))
-    bot.add_cog(Infractions(bot))
-    bot.add_cog(ModLog(bot))
-    bot.add_cog(ModManagement(bot))
-    bot.add_cog(Silence(bot))
-    bot.add_cog(Slowmode(bot))
-    bot.add_cog(Superstarify(bot))
diff --git a/bot/cogs/sync/__init__.py b/bot/cogs/sync/__init__.py
deleted file mode 100644
index fe7df4e9b..000000000
--- a/bot/cogs/sync/__init__.py
+++ /dev/null
@@ -1,7 +0,0 @@
-from bot.bot import Bot
-from .cog import Sync
-
-
-def setup(bot: Bot) -> None:
-    """Load the Sync cog."""
-    bot.add_cog(Sync(bot))
diff --git a/bot/cogs/watchchannels/__init__.py b/bot/cogs/watchchannels/__init__.py
deleted file mode 100644
index 69d118df6..000000000
--- a/bot/cogs/watchchannels/__init__.py
+++ /dev/null
@@ -1,9 +0,0 @@
-from bot.bot import Bot
-from .bigbrother import BigBrother
-from .talentpool import TalentPool
-
-
-def setup(bot: Bot) -> None:
-    """Load the BigBrother and TalentPool cogs."""
-    bot.add_cog(BigBrother(bot))
-    bot.add_cog(TalentPool(bot))
diff --git a/bot/constants.py b/bot/constants.py
index aec0ffce3..0cb076d5c 100644
--- a/bot/constants.py
+++ b/bot/constants.py
@@ -217,6 +217,7 @@ class Filter(metaclass=YAMLGetter):
     filter_zalgo: bool
     filter_invites: bool
     filter_domains: bool
+    filter_everyone_ping: bool
     watch_regex: bool
     watch_rich_embeds: bool
 
@@ -224,6 +225,7 @@ class Filter(metaclass=YAMLGetter):
     notify_user_zalgo: bool
     notify_user_invites: bool
     notify_user_domains: bool
+    notify_user_everyone_ping: bool
 
     ping_everyone: bool
     offensive_msg_delete_days: int
diff --git a/bot/decorators.py b/bot/decorators.py
index 500197c89..2518124da 100644
--- a/bot/decorators.py
+++ b/bot/decorators.py
@@ -6,13 +6,12 @@ from functools import wraps
 from typing import Callable, Container, Optional, Union
 from weakref import WeakValueDictionary
 
-from discord import Colour, Embed, Member
-from discord.errors import NotFound
+from discord import Colour, Embed, Member, NotFound
 from discord.ext import commands
 from discord.ext.commands import Cog, Context
 
 from bot.constants import Channels, ERROR_REPLIES, RedirectOutput
-from bot.utils.checks import in_whitelist_check, with_role_check, without_role_check
+from bot.utils.checks import in_whitelist_check
 
 log = logging.getLogger(__name__)
 
@@ -45,18 +44,22 @@ def in_whitelist(
     return commands.check(predicate)
 
 
-def with_role(*role_ids: int) -> Callable:
-    """Returns True if the user has any one of the roles in role_ids."""
-    async def predicate(ctx: Context) -> bool:
-        """With role checker predicate."""
-        return with_role_check(ctx, *role_ids)
-    return commands.check(predicate)
-
+def has_no_roles(*roles: Union[str, int]) -> Callable:
+    """
+    Returns True if the user does not have any of the roles specified.
 
-def without_role(*role_ids: int) -> Callable:
-    """Returns True if the user does not have any of the roles in role_ids."""
+    `roles` are the names or IDs of the disallowed roles.
+    """
     async def predicate(ctx: Context) -> bool:
-        return without_role_check(ctx, *role_ids)
+        try:
+            await commands.has_any_role(*roles).predicate(ctx)
+        except commands.MissingAnyRole:
+            return True
+        else:
+            # This error is never shown to users, so don't bother trying to make it too pretty.
+            roles_ = ", ".join(f"'{item}'" for item in roles)
+            raise commands.CheckFailure(f"You have at least one of the disallowed roles: {roles_}")
+
     return commands.check(predicate)
 
 
diff --git a/bot/cogs/__init__.py b/bot/exts/__init__.py
index e69de29bb..e69de29bb 100644
--- a/bot/cogs/__init__.py
+++ b/bot/exts/__init__.py
diff --git a/tests/bot/cogs/__init__.py b/bot/exts/backend/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/bot/cogs/__init__.py
+++ b/bot/exts/backend/__init__.py
diff --git a/bot/cogs/alias.py b/bot/exts/backend/alias.py
index c6ba8d6f3..c6ba8d6f3 100644
--- a/bot/cogs/alias.py
+++ b/bot/exts/backend/alias.py
diff --git a/bot/cogs/config_verifier.py b/bot/exts/backend/config_verifier.py
index d72c6c22e..d72c6c22e 100644
--- a/bot/cogs/config_verifier.py
+++ b/bot/exts/backend/config_verifier.py
diff --git a/bot/cogs/error_handler.py b/bot/exts/backend/error_handler.py
index f9d4de638..f9d4de638 100644
--- a/bot/cogs/error_handler.py
+++ b/bot/exts/backend/error_handler.py
diff --git a/bot/cogs/logging.py b/bot/exts/backend/logging.py
index 94fa2b139..94fa2b139 100644
--- a/bot/cogs/logging.py
+++ b/bot/exts/backend/logging.py
diff --git a/bot/exts/backend/sync/__init__.py b/bot/exts/backend/sync/__init__.py
new file mode 100644
index 000000000..829098f79
--- /dev/null
+++ b/bot/exts/backend/sync/__init__.py
@@ -0,0 +1,8 @@
+from bot.bot import Bot
+
+
+def setup(bot: Bot) -> None:
+    """Load the Sync cog."""
+    # Defer import to reduce side effects from importing the sync package.
+    from bot.exts.backend.sync._cog import Sync
+    bot.add_cog(Sync(bot))
diff --git a/bot/cogs/sync/cog.py b/bot/exts/backend/sync/_cog.py
index 5ace957e7..6e85e2b7d 100644
--- a/bot/cogs/sync/cog.py
+++ b/bot/exts/backend/sync/_cog.py
@@ -8,7 +8,7 @@ from discord.ext.commands import Cog, Context
 from bot import constants
 from bot.api import ResponseCodeError
 from bot.bot import Bot
-from bot.cogs.sync import syncers
+from bot.exts.backend.sync import _syncers
 
 log = logging.getLogger(__name__)
 
@@ -18,8 +18,8 @@ class Sync(Cog):
 
     def __init__(self, bot: Bot) -> None:
         self.bot = bot
-        self.role_syncer = syncers.RoleSyncer(self.bot)
-        self.user_syncer = syncers.UserSyncer(self.bot)
+        self.role_syncer = _syncers.RoleSyncer(self.bot)
+        self.user_syncer = _syncers.UserSyncer(self.bot)
 
         self.bot.loop.create_task(self.sync_guild())
 
diff --git a/bot/cogs/sync/syncers.py b/bot/exts/backend/sync/_syncers.py
index f7ba811bc..f7ba811bc 100644
--- a/bot/cogs/sync/syncers.py
+++ b/bot/exts/backend/sync/_syncers.py
diff --git a/tests/bot/cogs/moderation/__init__.py b/bot/exts/filters/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/bot/cogs/moderation/__init__.py
+++ b/bot/exts/filters/__init__.py
diff --git a/bot/cogs/antimalware.py b/bot/exts/filters/antimalware.py
index 7894ec48f..7894ec48f 100644
--- a/bot/cogs/antimalware.py
+++ b/bot/exts/filters/antimalware.py
diff --git a/bot/cogs/antispam.py b/bot/exts/filters/antispam.py
index 3ad487d8c..f2a2689e1 100644
--- a/bot/cogs/antispam.py
+++ b/bot/exts/filters/antispam.py
@@ -11,7 +11,6 @@ from discord.ext.commands import Cog
 
 from bot import rules
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
 from bot.constants import (
     AntiSpam as AntiSpamConfig, Channels,
     Colours, DEBUG_MODE, Event, Filter,
@@ -19,6 +18,7 @@ from bot.constants import (
     STAFF_ROLES,
 )
 from bot.converters import Duration
+from bot.exts.moderation.modlog import ModLog
 from bot.utils.messages import send_attachments
 
 
@@ -36,9 +36,6 @@ RULE_FUNCTION_MAPPING = {
     'mentions': rules.apply_mentions,
     'newlines': rules.apply_newlines,
     'role_mentions': rules.apply_role_mentions,
-    # the everyone filter is temporarily disabled until
-    # it has been improved.
-    # 'everyone_ping': rules.apply_everyone_ping,
 }
 
 
diff --git a/bot/cogs/filter_lists.py b/bot/exts/filters/filter_lists.py
index c15adc461..232c1e48b 100644
--- a/bot/cogs/filter_lists.py
+++ b/bot/exts/filters/filter_lists.py
@@ -2,14 +2,13 @@ import logging
 from typing import Optional
 
 from discord import Colour, Embed
-from discord.ext.commands import BadArgument, Cog, Context, IDConverter, group
+from discord.ext.commands import BadArgument, Cog, Context, IDConverter, group, has_any_role
 
 from bot import constants
 from bot.api import ResponseCodeError
 from bot.bot import Bot
 from bot.converters import ValidDiscordServerInvite, ValidFilterListType
 from bot.pagination import LinePaginator
-from bot.utils.checks import with_role_check
 
 log = logging.getLogger(__name__)
 
@@ -263,9 +262,9 @@ class FilterLists(Cog):
         """Syncs both allowlists and denylists with the API."""
         await self._sync_data(ctx)
 
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators to invoke the commands in this cog."""
-        return with_role_check(ctx, *constants.MODERATION_ROLES)
+        return await has_any_role(*constants.MODERATION_ROLES).predicate(ctx)
 
 
 def setup(bot: Bot) -> None:
diff --git a/bot/cogs/filtering.py b/bot/exts/filters/filtering.py
index 99b659bff..3bf0d88a0 100644
--- a/bot/cogs/filtering.py
+++ b/bot/exts/filters/filtering.py
@@ -13,11 +13,11 @@ from discord.utils import escape_markdown
 
 from bot.api import ResponseCodeError
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
 from bot.constants import (
-    Channels, Colours,
-    Filter, Icons, URLs
+    Channels, Colours, Filter,
+    Guild, Icons, URLs
 )
+from bot.exts.moderation.modlog import ModLog
 from bot.utils.redis_cache import RedisCache
 from bot.utils.regex import INVITE_RE
 from bot.utils.scheduling import Scheduler
@@ -25,6 +25,12 @@ from bot.utils.scheduling import Scheduler
 log = logging.getLogger(__name__)
 
 # Regular expressions
+CODE_BLOCK_RE = re.compile(
+    r"(?P<delim>``?)[^`]+?(?P=delim)(?!`+)"  # Inline codeblock
+    r"|```(.+?)```",  # Multiline codeblock
+    re.DOTALL | re.MULTILINE
+)
+EVERYONE_PING_RE = re.compile(rf"@everyone|<@&{Guild.id}>|@here")
 SPOILER_RE = re.compile(r"(\|\|.+?\|\|)", re.DOTALL)
 URL_RE = re.compile(r"(https?://[^\s]+)", flags=re.IGNORECASE)
 ZALGO_RE = re.compile(r"[\u0300-\u036F\u0489]")
@@ -82,6 +88,19 @@ class Filtering(Cog):
                 ),
                 "schedule_deletion": False
             },
+            "filter_everyone_ping": {
+                "enabled": Filter.filter_everyone_ping,
+                "function": self._has_everyone_ping,
+                "type": "filter",
+                "content_only": True,
+                "user_notification": Filter.notify_user_everyone_ping,
+                "notification_msg": (
+                    "Please don't try to ping `@everyone` or `@here`. "
+                    f"Your message has been removed. {staff_mistake_str}"
+                ),
+                "schedule_deletion": False,
+                "ping_everyone": False
+            },
             "watch_regex": {
                 "enabled": Filter.watch_regex,
                 "function": self._has_watch_regex_match,
@@ -332,6 +351,9 @@ class Filtering(Cog):
 
                         log.debug(message)
 
+                        # Allow specific filters to override ping_everyone
+                        ping_everyone = Filter.ping_everyone and _filter.get("ping_everyone", True)
+
                         # Send pretty mod log embed to mod-alerts
                         await self.mod_log.send_log_message(
                             icon_url=Icons.filtering,
@@ -340,7 +362,7 @@ class Filtering(Cog):
                             text=message,
                             thumbnail=msg.author.avatar_url_as(static_format="png"),
                             channel_id=Channels.mod_alerts,
-                            ping_everyone=Filter.ping_everyone if not is_private else False,
+                            ping_everyone=ping_everyone if not is_private else False,
                             additional_embeds=additional_embeds,
                             additional_embeds_msg=additional_embeds_msg
                         )
@@ -528,6 +550,16 @@ class Filtering(Cog):
                         return False
         return False
 
+    @staticmethod
+    async def _has_everyone_ping(text: str) -> bool:
+        """Determines if `msg` contains an @everyone or @here ping outside of a codeblock."""
+        # First pass to avoid running re.sub on every message
+        if not EVERYONE_PING_RE.search(text):
+            return False
+
+        content_without_codeblocks = CODE_BLOCK_RE.sub("", text)
+        return bool(EVERYONE_PING_RE.search(content_without_codeblocks))
+
     async def notify_member(self, filtered_member: Member, reason: str, channel: TextChannel) -> None:
         """
         Notify filtered_member about a moderation action with the reason str.
diff --git a/bot/cogs/security.py b/bot/exts/filters/security.py
index c680c5e27..c680c5e27 100644
--- a/bot/cogs/security.py
+++ b/bot/exts/filters/security.py
diff --git a/bot/cogs/token_remover.py b/bot/exts/filters/token_remover.py
index ef979f222..0eda3dc6a 100644
--- a/bot/cogs/token_remover.py
+++ b/bot/exts/filters/token_remover.py
@@ -9,8 +9,8 @@ from discord.ext.commands import Cog
 
 from bot import utils
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
 from bot.constants import Channels, Colours, Event, Icons
+from bot.exts.moderation.modlog import ModLog
 
 log = logging.getLogger(__name__)
 
diff --git a/bot/cogs/webhook_remover.py b/bot/exts/filters/webhook_remover.py
index 5812da87c..ca126ebf5 100644
--- a/bot/cogs/webhook_remover.py
+++ b/bot/exts/filters/webhook_remover.py
@@ -5,8 +5,8 @@ from discord import Colour, Message, NotFound
 from discord.ext.commands import Cog
 
 from bot.bot import Bot
-from bot.cogs.moderation.modlog import ModLog
 from bot.constants import Channels, Colours, Event, Icons
+from bot.exts.moderation.modlog import ModLog
 
 WEBHOOK_URL_RE = re.compile(r"((?:https?://)?discord(?:app)?\.com/api/webhooks/\d+/)\S+/?", re.IGNORECASE)
 
diff --git a/tests/bot/cogs/sync/__init__.py b/bot/exts/fun/__init__.py
index e69de29bb..e69de29bb 100644
--- a/tests/bot/cogs/sync/__init__.py
+++ b/bot/exts/fun/__init__.py
diff --git a/bot/cogs/duck_pond.py b/bot/exts/fun/duck_pond.py
index 2758de8ab..2758de8ab 100644
--- a/bot/cogs/duck_pond.py
+++ b/bot/exts/fun/duck_pond.py
diff --git a/bot/cogs/off_topic_names.py b/bot/exts/fun/off_topic_names.py
index ce95450e0..b9d235fa2 100644
--- a/bot/cogs/off_topic_names.py
+++ b/bot/exts/fun/off_topic_names.py
@@ -4,13 +4,12 @@ import logging
 from datetime import datetime, timedelta
 
 from discord import Colour, Embed
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.api import ResponseCodeError
 from bot.bot import Bot
 from bot.constants import Channels, MODERATION_ROLES
 from bot.converters import OffTopicName
-from bot.decorators import with_role
 from bot.pagination import LinePaginator
 
 CHANNELS = (Channels.off_topic_0, Channels.off_topic_1, Channels.off_topic_2)
@@ -67,13 +66,13 @@ class OffTopicNames(Cog):
             self.updater_task = self.bot.loop.create_task(coro)
 
     @group(name='otname', aliases=('otnames', 'otn'), invoke_without_command=True)
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def otname_group(self, ctx: Context) -> None:
         """Add or list items from the off-topic channel name rotation."""
         await ctx.send_help(ctx.command)
 
     @otname_group.command(name='add', aliases=('a',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def add_command(self, ctx: Context, *, name: OffTopicName) -> None:
         """
         Adds a new off-topic name to the rotation.
@@ -96,7 +95,7 @@ class OffTopicNames(Cog):
             await self._add_name(ctx, name)
 
     @otname_group.command(name='forceadd', aliases=('fa',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def force_add_command(self, ctx: Context, *, name: OffTopicName) -> None:
         """Forcefully adds a new off-topic name to the rotation."""
         await self._add_name(ctx, name)
@@ -109,7 +108,7 @@ class OffTopicNames(Cog):
         await ctx.send(f":ok_hand: Added `{name}` to the names list.")
 
     @otname_group.command(name='delete', aliases=('remove', 'rm', 'del', 'd'))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def delete_command(self, ctx: Context, *, name: OffTopicName) -> None:
         """Removes a off-topic name from the rotation."""
         await self.bot.api_client.delete(f'bot/off-topic-channel-names/{name}')
@@ -118,7 +117,7 @@ class OffTopicNames(Cog):
         await ctx.send(f":ok_hand: Removed `{name}` from the names list.")
 
     @otname_group.command(name='list', aliases=('l',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def list_command(self, ctx: Context) -> None:
         """
         Lists all currently known off-topic channel names in a paginator.
@@ -138,7 +137,7 @@ class OffTopicNames(Cog):
             await ctx.send(embed=embed)
 
     @otname_group.command(name='search', aliases=('s',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def search_command(self, ctx: Context, *, query: OffTopicName) -> None:
         """Search for an off-topic name."""
         result = await self.bot.api_client.get('bot/off-topic-channel-names')
diff --git a/bot/cogs/help_channels.py b/bot/exts/help_channels.py
index 0f9cac89e..17142071f 100644
--- a/bot/cogs/help_channels.py
+++ b/bot/exts/help_channels.py
@@ -14,7 +14,6 @@ from discord.ext import commands
 from bot import constants
 from bot.bot import Bot
 from bot.utils import RedisCache
-from bot.utils.checks import with_role_check
 from bot.utils.scheduling import Scheduler
 
 log = logging.getLogger(__name__)
@@ -196,12 +195,12 @@ class HelpChannels(commands.Cog):
             return True
 
         log.trace(f"{ctx.author} is not the help channel claimant, checking roles.")
-        role_check = with_role_check(ctx, *constants.HelpChannels.cmd_whitelist)
+        has_role = await commands.has_any_role(*constants.HelpChannels.cmd_whitelist).predicate(ctx)
 
-        if role_check:
+        if has_role:
             self.bot.stats.incr("help.dormant_invoke.staff")
 
-        return role_check
+        return has_role
 
     @commands.command(name="close", aliases=["dormant", "solved"], enabled=False)
     async def close_command(self, ctx: commands.Context) -> None:
diff --git a/bot/exts/info/__init__.py b/bot/exts/info/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/bot/exts/info/__init__.py
diff --git a/bot/cogs/doc.py b/bot/exts/info/doc.py
index 30c793c75..e50b9b32b 100644
--- a/bot/cogs/doc.py
+++ b/bot/exts/info/doc.py
@@ -21,7 +21,6 @@ from urllib3.exceptions import ProtocolError
 from bot.bot import Bot
 from bot.constants import MODERATION_ROLES, RedirectOutput
 from bot.converters import ValidPythonIdentifier, ValidURL
-from bot.decorators import with_role
 from bot.pagination import LinePaginator
 from bot.utils.messages import wait_for_deletion
 
@@ -396,7 +395,7 @@ class Doc(commands.Cog):
                 await wait_for_deletion(msg, (ctx.author.id,), client=self.bot)
 
     @docs_group.command(name='set', aliases=('s',))
-    @with_role(*MODERATION_ROLES)
+    @commands.has_any_role(*MODERATION_ROLES)
     async def set_command(
         self, ctx: commands.Context, package_name: ValidPythonIdentifier,
         base_url: ValidURL, inventory_url: InventoryURL
@@ -433,7 +432,7 @@ class Doc(commands.Cog):
         await ctx.send(f"Added package `{package_name}` to database and refreshed inventory.")
 
     @docs_group.command(name='delete', aliases=('remove', 'rm', 'd'))
-    @with_role(*MODERATION_ROLES)
+    @commands.has_any_role(*MODERATION_ROLES)
     async def delete_command(self, ctx: commands.Context, package_name: ValidPythonIdentifier) -> None:
         """
         Removes the specified package from the database.
@@ -450,7 +449,7 @@ class Doc(commands.Cog):
         await ctx.send(f"Successfully deleted `{package_name}` and refreshed inventory.")
 
     @docs_group.command(name="refresh", aliases=("rfsh", "r"))
-    @with_role(*MODERATION_ROLES)
+    @commands.has_any_role(*MODERATION_ROLES)
     async def refresh_command(self, ctx: commands.Context) -> None:
         """Refresh inventories and send differences to channel."""
         old_inventories = set(self.base_urls)
diff --git a/bot/cogs/help.py b/bot/exts/info/help.py
index 99d503f5c..99d503f5c 100644
--- a/bot/cogs/help.py
+++ b/bot/exts/info/help.py
diff --git a/bot/cogs/information.py b/bot/exts/info/information.py
index 55ecb2836..581b3a227 100644
--- a/bot/cogs/information.py
+++ b/bot/exts/info/information.py
@@ -8,18 +8,19 @@ from typing import Any, Mapping, Optional, Tuple, Union
 
 from discord import ChannelType, Colour, CustomActivity, Embed, Guild, Member, Message, Role, Status, utils
 from discord.abc import GuildChannel
-from discord.ext.commands import BucketType, Cog, Context, Paginator, command, group
+from discord.ext.commands import BucketType, Cog, Context, Paginator, command, group, has_any_role
 from discord.utils import escape_markdown
 
 from bot import constants
 from bot.bot import Bot
-from bot.decorators import in_whitelist, with_role
+from bot.decorators import in_whitelist
 from bot.pagination import LinePaginator
-from bot.utils.checks import InWhitelistCheckFailure, cooldown_with_role_bypass, with_role_check
+from bot.utils.checks import InWhitelistCheckFailure, cooldown_with_role_bypass, has_no_roles_check
 from bot.utils.time import time_since
 
 log = logging.getLogger(__name__)
 
+
 STATUS_EMOTES = {
     Status.offline: constants.Emojis.status_offline,
     Status.dnd: constants.Emojis.status_dnd,
@@ -76,7 +77,7 @@ class Information(Cog):
         channel_type_list = sorted(channel_type_list)
         return "\n".join(channel_type_list)
 
-    @with_role(*constants.MODERATION_ROLES)
+    @has_any_role(*constants.MODERATION_ROLES)
     @command(name="roles")
     async def roles_info(self, ctx: Context) -> None:
         """Returns a list of all roles and their corresponding IDs."""
@@ -96,7 +97,7 @@ class Information(Cog):
 
         await LinePaginator.paginate(role_list, ctx, embed, empty=False)
 
-    @with_role(*constants.MODERATION_ROLES)
+    @has_any_role(*constants.MODERATION_ROLES)
     @command(name="role")
     async def role_info(self, ctx: Context, *roles: Union[Role, str]) -> None:
         """
@@ -197,12 +198,12 @@ class Information(Cog):
             user = ctx.author
 
         # Do a role check if this is being executed on someone other than the caller
-        elif user != ctx.author and not with_role_check(ctx, *constants.MODERATION_ROLES):
+        elif user != ctx.author and await has_no_roles_check(ctx, *constants.MODERATION_ROLES):
             await ctx.send("You may not use this command on users other than yourself.")
             return
 
         # Non-staff may only do this in #bot-commands
-        if not with_role_check(ctx, *constants.STAFF_ROLES):
+        if await has_no_roles_check(ctx, *constants.STAFF_ROLES):
             if not ctx.channel.id == constants.Channels.bot_commands:
                 raise InWhitelistCheckFailure(constants.Channels.bot_commands)
 
diff --git a/bot/cogs/python_news.py b/bot/exts/info/python_news.py
index 0ab5738a4..0ab5738a4 100644
--- a/bot/cogs/python_news.py
+++ b/bot/exts/info/python_news.py
diff --git a/bot/cogs/reddit.py b/bot/exts/info/reddit.py
index 5d9e2c20b..635162308 100644
--- a/bot/cogs/reddit.py
+++ b/bot/exts/info/reddit.py
@@ -8,14 +8,13 @@ from typing import List
 
 from aiohttp import BasicAuth, ClientError
 from discord import Colour, Embed, TextChannel
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 from discord.ext.tasks import loop
 from discord.utils import escape_markdown
 
 from bot.bot import Bot
 from bot.constants import Channels, ERROR_REPLIES, Emojis, Reddit as RedditConfig, STAFF_ROLES, Webhooks
 from bot.converters import Subreddit
-from bot.decorators import with_role
 from bot.pagination import LinePaginator
 from bot.utils.messages import sub_clyde
 
@@ -282,7 +281,7 @@ class Reddit(Cog):
 
         await ctx.send(content=f"Here are this week's top {subreddit} posts!", embed=embed)
 
-    @with_role(*STAFF_ROLES)
+    @has_any_role(*STAFF_ROLES)
     @reddit_group.command(name="subreddits", aliases=("subs",))
     async def subreddits_command(self, ctx: Context) -> None:
         """Send a paginated embed of all the subreddits we're relaying."""
diff --git a/bot/cogs/site.py b/bot/exts/info/site.py
index 2d3a3d9f3..2d3a3d9f3 100644
--- a/bot/cogs/site.py
+++ b/bot/exts/info/site.py
diff --git a/bot/cogs/source.py b/bot/exts/info/source.py
index 205e0ba81..205e0ba81 100644
--- a/bot/cogs/source.py
+++ b/bot/exts/info/source.py
diff --git a/bot/cogs/stats.py b/bot/exts/info/stats.py
index d42f55466..d42f55466 100644
--- a/bot/cogs/stats.py
+++ b/bot/exts/info/stats.py
diff --git a/bot/cogs/tags.py b/bot/exts/info/tags.py
index d01647312..d01647312 100644
--- a/bot/cogs/tags.py
+++ b/bot/exts/info/tags.py
diff --git a/bot/exts/moderation/__init__.py b/bot/exts/moderation/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/bot/exts/moderation/__init__.py
diff --git a/bot/cogs/defcon.py b/bot/exts/moderation/defcon.py
index 9087ac454..3bf462877 100644
--- a/bot/cogs/defcon.py
+++ b/bot/exts/moderation/defcon.py
@@ -6,12 +6,11 @@ from datetime import datetime, timedelta
 from enum import Enum
 
 from discord import Colour, Embed, Member
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
 from bot.constants import Channels, Colours, Emojis, Event, Icons, MODERATION_ROLES, Roles
-from bot.decorators import with_role
+from bot.exts.moderation.modlog import ModLog
 
 log = logging.getLogger(__name__)
 
@@ -119,7 +118,7 @@ class Defcon(Cog):
                 )
 
     @group(name='defcon', aliases=('dc',), invoke_without_command=True)
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def defcon_group(self, ctx: Context) -> None:
         """Check the DEFCON status or run a subcommand."""
         await ctx.send_help(ctx.command)
@@ -163,7 +162,7 @@ class Defcon(Cog):
             self.bot.stats.gauge("defcon.threshold", days)
 
     @defcon_group.command(name='enable', aliases=('on', 'e'), root_aliases=("defon",))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def enable_command(self, ctx: Context) -> None:
         """
         Enable DEFCON mode. Useful in a pinch, but be sure you know what you're doing!
@@ -176,7 +175,7 @@ class Defcon(Cog):
         await self.update_channel_topic()
 
     @defcon_group.command(name='disable', aliases=('off', 'd'), root_aliases=("defoff",))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def disable_command(self, ctx: Context) -> None:
         """Disable DEFCON mode. Useful in a pinch, but be sure you know what you're doing!"""
         self.enabled = False
@@ -184,7 +183,7 @@ class Defcon(Cog):
         await self.update_channel_topic()
 
     @defcon_group.command(name='status', aliases=('s',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def status_command(self, ctx: Context) -> None:
         """Check the current status of DEFCON mode."""
         embed = Embed(
@@ -196,7 +195,7 @@ class Defcon(Cog):
         await ctx.send(embed=embed)
 
     @defcon_group.command(name='days')
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def days_command(self, ctx: Context, days: int) -> None:
         """Set how old an account must be to join the server, in days, with DEFCON mode enabled."""
         self.days = timedelta(days=days)
diff --git a/bot/cogs/dm_relay.py b/bot/exts/moderation/dm_relay.py
index 0d8f340b4..7a3fe49bb 100644
--- a/bot/cogs/dm_relay.py
+++ b/bot/exts/moderation/dm_relay.py
@@ -10,7 +10,7 @@ from bot import constants
 from bot.bot import Bot
 from bot.converters import UserMentionOrID
 from bot.utils import RedisCache
-from bot.utils.checks import in_whitelist_check, with_role_check
+from bot.utils.checks import in_whitelist_check
 from bot.utils.messages import send_attachments
 from bot.utils.webhooks import send_webhook
 
@@ -105,10 +105,10 @@ class DMRelay(Cog):
             except discord.HTTPException:
                 log.exception("Failed to send an attachment to the webhook")
 
-    def cog_check(self, ctx: commands.Context) -> bool:
+    async def cog_check(self, ctx: commands.Context) -> bool:
         """Only allow moderators to invoke the commands in this cog."""
         checks = [
-            with_role_check(ctx, *constants.MODERATION_ROLES),
+            await commands.has_any_role(*constants.MODERATION_ROLES).predicate(ctx),
             in_whitelist_check(
                 ctx,
                 channels=[constants.Channels.dm_log],
diff --git a/bot/cogs/moderation/incidents.py b/bot/exts/moderation/incidents.py
index 3605ab1d2..e49913552 100644
--- a/bot/cogs/moderation/incidents.py
+++ b/bot/exts/moderation/incidents.py
@@ -405,3 +405,8 @@ class Incidents(Cog):
         """Pass `message` to `add_signals` if and only if it satisfies `is_incident`."""
         if is_incident(message):
             await add_signals(message)
+
+
+def setup(bot: Bot) -> None:
+    """Load the Incidents cog."""
+    bot.add_cog(Incidents(bot))
diff --git a/bot/exts/moderation/infraction/__init__.py b/bot/exts/moderation/infraction/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/bot/exts/moderation/infraction/__init__.py
diff --git a/bot/cogs/moderation/scheduler.py b/bot/exts/moderation/infraction/_scheduler.py
index 051f6c52c..cf48ef2ac 100644
--- a/bot/cogs/moderation/scheduler.py
+++ b/bot/exts/moderation/infraction/_scheduler.py
@@ -13,11 +13,11 @@ from bot import constants
 from bot.api import ResponseCodeError
 from bot.bot import Bot
 from bot.constants import Colours, STAFF_CHANNELS
+from bot.exts.moderation.infraction import _utils
+from bot.exts.moderation.infraction._utils import UserSnowflake
+from bot.exts.moderation.modlog import ModLog
 from bot.utils import time
 from bot.utils.scheduling import Scheduler
-from . import utils
-from .modlog import ModLog
-from .utils import UserSnowflake
 
 log = logging.getLogger(__name__)
 
@@ -56,7 +56,7 @@ class InfractionScheduler:
 
     async def reapply_infraction(
         self,
-        infraction: utils.Infraction,
+        infraction: _utils.Infraction,
         apply_coro: t.Optional[t.Awaitable]
     ) -> None:
         """Reapply an infraction if it's still active or deactivate it if less than 60 sec left."""
@@ -80,13 +80,13 @@ class InfractionScheduler:
     async def apply_infraction(
         self,
         ctx: Context,
-        infraction: utils.Infraction,
+        infraction: _utils.Infraction,
         user: UserSnowflake,
         action_coro: t.Optional[t.Awaitable] = None
     ) -> None:
         """Apply an infraction to the user, log the infraction, and optionally notify the user."""
         infr_type = infraction["type"]
-        icon = utils.INFRACTION_ICONS[infr_type][0]
+        icon = _utils.INFRACTION_ICONS[infr_type][0]
         reason = infraction["reason"]
         expiry = time.format_infraction_with_duration(infraction["expires_at"])
         id_ = infraction['id']
@@ -126,7 +126,7 @@ class InfractionScheduler:
                 log.error(f"Failed to DM {user.id}: could not fetch user (status {e.status})")
             else:
                 # Accordingly display whether the user was successfully notified via DM.
-                if await utils.notify_infraction(user, infr_type, expiry, reason, icon):
+                if await _utils.notify_infraction(user, infr_type, expiry, reason, icon):
                     dm_result = ":incoming_envelope: "
                     dm_log_text = "\nDM: Sent"
 
@@ -318,7 +318,7 @@ class InfractionScheduler:
 
         # Send a log message to the mod log.
         await self.mod_log.send_log_message(
-            icon_url=utils.INFRACTION_ICONS[infr_type][1],
+            icon_url=_utils.INFRACTION_ICONS[infr_type][1],
             colour=Colours.soft_green,
             title=f"Infraction {log_title}: {infr_type}",
             thumbnail=user.avatar_url_as(static_format="png"),
@@ -329,7 +329,7 @@ class InfractionScheduler:
 
     async def deactivate_infraction(
         self,
-        infraction: utils.Infraction,
+        infraction: _utils.Infraction,
         send_log: bool = True
     ) -> t.Dict[str, str]:
         """
@@ -434,7 +434,7 @@ class InfractionScheduler:
 
             log.trace(f"Sending deactivation mod log for infraction #{id_}.")
             await self.mod_log.send_log_message(
-                icon_url=utils.INFRACTION_ICONS[type_][1],
+                icon_url=_utils.INFRACTION_ICONS[type_][1],
                 colour=Colours.soft_green,
                 title=f"Infraction {log_title}: {type_}",
                 thumbnail=avatar,
@@ -446,7 +446,7 @@ class InfractionScheduler:
         return log_text
 
     @abstractmethod
-    async def _pardon_action(self, infraction: utils.Infraction) -> t.Optional[t.Dict[str, str]]:
+    async def _pardon_action(self, infraction: _utils.Infraction) -> t.Optional[t.Dict[str, str]]:
         """
         Execute deactivation steps specific to the infraction's type and return a log dict.
 
@@ -454,7 +454,7 @@ class InfractionScheduler:
         """
         raise NotImplementedError
 
-    def schedule_expiration(self, infraction: utils.Infraction) -> None:
+    def schedule_expiration(self, infraction: _utils.Infraction) -> None:
         """
         Marks an infraction expired after the delay from time of scheduling to time of expiration.
 
diff --git a/bot/cogs/moderation/utils.py b/bot/exts/moderation/infraction/_utils.py
index f21272102..1d91964f1 100644
--- a/bot/cogs/moderation/utils.py
+++ b/bot/exts/moderation/infraction/_utils.py
@@ -1,5 +1,4 @@
 import logging
-import textwrap
 import typing as t
 from datetime import datetime
 
@@ -28,6 +27,18 @@ UserObject = t.Union[discord.Member, discord.User]
 UserSnowflake = t.Union[UserObject, discord.Object]
 Infraction = t.Dict[str, t.Union[str, int, bool]]
 
+APPEAL_EMAIL = "[email protected]"
+
+INFRACTION_TITLE = f"Please review our rules over at {RULES_URL}"
+INFRACTION_APPEAL_FOOTER = f"To appeal this infraction, send an e-mail to {APPEAL_EMAIL}"
+INFRACTION_AUTHOR_NAME = "Infraction information"
+
+INFRACTION_DESCRIPTION_TEMPLATE = (
+    "**Type:** {type}\n"
+    "**Expires:** {expires}\n"
+    "**Reason:** {reason}\n"
+)
+
 
 async def post_user(ctx: Context, user: UserSnowflake) -> t.Optional[dict]:
     """
@@ -142,25 +153,27 @@ async def notify_infraction(
     """DM a user about their new infraction and return True if the DM is successful."""
     log.trace(f"Sending {user} a DM about their {infr_type} infraction.")
 
-    text = textwrap.dedent(f"""
-        **Type:** {infr_type.capitalize()}
-        **Expires:** {expires_at or "N/A"}
-        **Reason:** {reason or "No reason provided."}
-    """)
+    text = INFRACTION_DESCRIPTION_TEMPLATE.format(
+        type=infr_type.capitalize(),
+        expires=expires_at or "N/A",
+        reason=reason or "No reason provided."
+    )
+
+    # For case when other fields than reason is too long and this reach limit, then force-shorten string
+    if len(text) > 2048:
+        text = f"{text[:2045]}..."
 
     embed = discord.Embed(
-        description=textwrap.shorten(text, width=2048, placeholder="..."),
+        description=text,
         colour=Colours.soft_red
     )
 
-    embed.set_author(name="Infraction information", icon_url=icon_url, url=RULES_URL)
-    embed.title = f"Please review our rules over at {RULES_URL}"
+    embed.set_author(name=INFRACTION_AUTHOR_NAME, icon_url=icon_url, url=RULES_URL)
+    embed.title = INFRACTION_TITLE
     embed.url = RULES_URL
 
     if infr_type in APPEALABLE_INFRACTIONS:
-        embed.set_footer(
-            text="To appeal this infraction, send an e-mail to [email protected]"
-        )
+        embed.set_footer(text=INFRACTION_APPEAL_FOOTER)
 
     return await send_private_embed(user, embed)
 
diff --git a/bot/cogs/moderation/infractions.py b/bot/exts/moderation/infraction/infractions.py
index 8df642428..5fa62d3c4 100644
--- a/bot/cogs/moderation/infractions.py
+++ b/bot/exts/moderation/infraction/infractions.py
@@ -12,10 +12,9 @@ from bot.bot import Bot
 from bot.constants import Event
 from bot.converters import Expiry, FetchedMember
 from bot.decorators import respect_role_hierarchy
-from bot.utils.checks import with_role_check
-from . import utils
-from .scheduler import InfractionScheduler
-from .utils import UserSnowflake
+from bot.exts.moderation.infraction import _utils
+from bot.exts.moderation.infraction._scheduler import InfractionScheduler
+from bot.exts.moderation.infraction._utils import UserSnowflake
 
 log = logging.getLogger(__name__)
 
@@ -55,7 +54,7 @@ class Infractions(InfractionScheduler, commands.Cog):
     @command()
     async def warn(self, ctx: Context, user: Member, *, reason: t.Optional[str] = None) -> None:
         """Warn a user for the given reason."""
-        infraction = await utils.post_infraction(ctx, user, "warning", reason, active=False)
+        infraction = await _utils.post_infraction(ctx, user, "warning", reason, active=False)
         if infraction is None:
             return
 
@@ -125,7 +124,7 @@ class Infractions(InfractionScheduler, commands.Cog):
     @command(hidden=True)
     async def note(self, ctx: Context, user: FetchedMember, *, reason: t.Optional[str] = None) -> None:
         """Create a private note for a user with the given reason without notifying the user."""
-        infraction = await utils.post_infraction(ctx, user, "note", reason, hidden=True, active=False)
+        infraction = await _utils.post_infraction(ctx, user, "note", reason, hidden=True, active=False)
         if infraction is None:
             return
 
@@ -213,10 +212,10 @@ class Infractions(InfractionScheduler, commands.Cog):
 
     async def apply_mute(self, ctx: Context, user: Member, reason: t.Optional[str], **kwargs) -> None:
         """Apply a mute infraction with kwargs passed to `post_infraction`."""
-        if await utils.get_active_infraction(ctx, user, "mute"):
+        if await _utils.get_active_infraction(ctx, user, "mute"):
             return
 
-        infraction = await utils.post_infraction(ctx, user, "mute", reason, active=True, **kwargs)
+        infraction = await _utils.post_infraction(ctx, user, "mute", reason, active=True, **kwargs)
         if infraction is None:
             return
 
@@ -233,7 +232,7 @@ class Infractions(InfractionScheduler, commands.Cog):
     @respect_role_hierarchy()
     async def apply_kick(self, ctx: Context, user: Member, reason: t.Optional[str], **kwargs) -> None:
         """Apply a kick infraction with kwargs passed to `post_infraction`."""
-        infraction = await utils.post_infraction(ctx, user, "kick", reason, active=False, **kwargs)
+        infraction = await _utils.post_infraction(ctx, user, "kick", reason, active=False, **kwargs)
         if infraction is None:
             return
 
@@ -254,7 +253,7 @@ class Infractions(InfractionScheduler, commands.Cog):
         """
         # In the case of a permanent ban, we don't need get_active_infractions to tell us if one is active
         is_temporary = kwargs.get("expires_at") is not None
-        active_infraction = await utils.get_active_infraction(ctx, user, "ban", is_temporary)
+        active_infraction = await _utils.get_active_infraction(ctx, user, "ban", is_temporary)
 
         if active_infraction:
             if is_temporary:
@@ -269,7 +268,7 @@ class Infractions(InfractionScheduler, commands.Cog):
             log.trace("Old tempban is being replaced by new permaban.")
             await self.pardon_infraction(ctx, "ban", user, is_temporary)
 
-        infraction = await utils.post_infraction(ctx, user, "ban", reason, active=True, **kwargs)
+        infraction = await _utils.post_infraction(ctx, user, "ban", reason, active=True, **kwargs)
         if infraction is None:
             return
 
@@ -309,11 +308,11 @@ class Infractions(InfractionScheduler, commands.Cog):
             await user.remove_roles(self._muted_role, reason=reason)
 
             # DM the user about the expiration.
-            notified = await utils.notify_pardon(
+            notified = await _utils.notify_pardon(
                 user=user,
                 title="You have been unmuted",
                 content="You may now send messages in the server.",
-                icon_url=utils.INFRACTION_ICONS["mute"][1]
+                icon_url=_utils.INFRACTION_ICONS["mute"][1]
             )
 
             log_text["Member"] = f"{user.mention}(`{user.id}`)"
@@ -339,7 +338,7 @@ class Infractions(InfractionScheduler, commands.Cog):
 
         return log_text
 
-    async def _pardon_action(self, infraction: utils.Infraction) -> t.Optional[t.Dict[str, str]]:
+    async def _pardon_action(self, infraction: _utils.Infraction) -> t.Optional[t.Dict[str, str]]:
         """
         Execute deactivation steps specific to the infraction's type and return a log dict.
 
@@ -357,9 +356,9 @@ class Infractions(InfractionScheduler, commands.Cog):
     # endregion
 
     # This cannot be static (must have a __func__ attribute).
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators to invoke the commands in this cog."""
-        return with_role_check(ctx, *constants.MODERATION_ROLES)
+        return await commands.has_any_role(*constants.MODERATION_ROLES).predicate(ctx)
 
     # This cannot be static (must have a __func__ attribute).
     async def cog_command_error(self, ctx: Context, error: Exception) -> None:
@@ -368,3 +367,8 @@ class Infractions(InfractionScheduler, commands.Cog):
             if discord.User in error.converters or discord.Member in error.converters:
                 await ctx.send(str(error.errors[0]))
                 error.handled = True
+
+
+def setup(bot: Bot) -> None:
+    """Load the Infractions cog."""
+    bot.add_cog(Infractions(bot))
diff --git a/bot/cogs/moderation/management.py b/bot/exts/moderation/infraction/management.py
index 672bb0e9c..15ee28537 100644
--- a/bot/cogs/moderation/management.py
+++ b/bot/exts/moderation/infraction/management.py
@@ -10,12 +10,12 @@ from discord.ext.commands import Context
 from bot import constants
 from bot.bot import Bot
 from bot.converters import Expiry, InfractionSearchQuery, allowed_strings, proxy_user
+from bot.exts.moderation.infraction import _utils
+from bot.exts.moderation.infraction.infractions import Infractions
+from bot.exts.moderation.modlog import ModLog
 from bot.pagination import LinePaginator
 from bot.utils import time
-from bot.utils.checks import in_whitelist_check, with_role_check
-from . import utils
-from .infractions import Infractions
-from .modlog import ModLog
+from bot.utils.checks import in_whitelist_check
 
 log = logging.getLogger(__name__)
 
@@ -220,7 +220,7 @@ class ModManagement(commands.Cog):
         self,
         ctx: Context,
         embed: discord.Embed,
-        infractions: t.Iterable[utils.Infraction]
+        infractions: t.Iterable[_utils.Infraction]
     ) -> None:
         """Send a paginated embed of infractions for the specified user."""
         if not infractions:
@@ -241,7 +241,7 @@ class ModManagement(commands.Cog):
             max_size=1000
         )
 
-    def infraction_to_string(self, infraction: utils.Infraction) -> str:
+    def infraction_to_string(self, infraction: _utils.Infraction) -> str:
         """Convert the infraction object to a string representation."""
         actor_id = infraction["actor"]
         guild = self.bot.get_guild(constants.Guild.id)
@@ -282,10 +282,10 @@ class ModManagement(commands.Cog):
     # endregion
 
     # This cannot be static (must have a __func__ attribute).
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators inside moderator channels to invoke the commands in this cog."""
         checks = [
-            with_role_check(ctx, *constants.MODERATION_ROLES),
+            await commands.has_any_role(*constants.MODERATION_ROLES).predicate(ctx),
             in_whitelist_check(
                 ctx,
                 channels=constants.MODERATION_CHANNELS,
@@ -303,3 +303,8 @@ class ModManagement(commands.Cog):
             if discord.User in error.converters:
                 await ctx.send(str(error.errors[0]))
                 error.handled = True
+
+
+def setup(bot: Bot) -> None:
+    """Load the ModManagement cog."""
+    bot.add_cog(ModManagement(bot))
diff --git a/bot/cogs/moderation/superstarify.py b/bot/exts/moderation/infraction/superstarify.py
index 867de815a..29f41f2ab 100644
--- a/bot/cogs/moderation/superstarify.py
+++ b/bot/exts/moderation/infraction/superstarify.py
@@ -6,15 +6,14 @@ import typing as t
 from pathlib import Path
 
 from discord import Colour, Embed, Member
-from discord.ext.commands import Cog, Context, command
+from discord.ext.commands import Cog, Context, command, has_any_role
 
 from bot import constants
 from bot.bot import Bot
 from bot.converters import Expiry
-from bot.utils.checks import with_role_check
+from bot.exts.moderation.infraction import _utils
+from bot.exts.moderation.infraction._scheduler import InfractionScheduler
 from bot.utils.time import format_infraction
-from . import utils
-from .scheduler import InfractionScheduler
 
 log = logging.getLogger(__name__)
 NICKNAME_POLICY_URL = "https://pythondiscord.com/pages/rules/#nickname-policy"
@@ -67,7 +66,7 @@ class Superstarify(InfractionScheduler, Cog):
             reason=f"Superstarified member tried to escape the prison: {infraction['id']}"
         )
 
-        notified = await utils.notify_infraction(
+        notified = await _utils.notify_infraction(
             user=after,
             infr_type="Superstarify",
             expires_at=format_infraction(infraction["expires_at"]),
@@ -76,7 +75,7 @@ class Superstarify(InfractionScheduler, Cog):
                 f"from **{before.display_name}** to **{after.display_name}**, but as you "
                 "are currently in superstar-prison, you do not have permission to do so."
             ),
-            icon_url=utils.INFRACTION_ICONS["superstar"][0]
+            icon_url=_utils.INFRACTION_ICONS["superstar"][0]
         )
 
         if not notified:
@@ -130,12 +129,12 @@ class Superstarify(InfractionScheduler, Cog):
         An optional reason can be provided. If no reason is given, the original name will be shown
         in a generated reason.
         """
-        if await utils.get_active_infraction(ctx, member, "superstar"):
+        if await _utils.get_active_infraction(ctx, member, "superstar"):
             return
 
         # Post the infraction to the API
         reason = reason or f"old nick: {member.display_name}"
-        infraction = await utils.post_infraction(ctx, member, "superstar", reason, duration, active=True)
+        infraction = await _utils.post_infraction(ctx, member, "superstar", reason, duration, active=True)
         id_ = infraction["id"]
 
         old_nick = member.display_name
@@ -149,11 +148,11 @@ class Superstarify(InfractionScheduler, Cog):
         self.schedule_expiration(infraction)
 
         # Send a DM to the user to notify them of their new infraction.
-        await utils.notify_infraction(
+        await _utils.notify_infraction(
             user=member,
             infr_type="Superstarify",
             expires_at=expiry_str,
-            icon_url=utils.INFRACTION_ICONS["superstar"][0],
+            icon_url=_utils.INFRACTION_ICONS["superstar"][0],
             reason=f"Your nickname didn't comply with our [nickname policy]({NICKNAME_POLICY_URL})."
         )
 
@@ -176,7 +175,7 @@ class Superstarify(InfractionScheduler, Cog):
         # Log to the mod log channel.
         log.trace(f"Sending apply mod log for superstar #{id_}.")
         await self.mod_log.send_log_message(
-            icon_url=utils.INFRACTION_ICONS["superstar"][0],
+            icon_url=_utils.INFRACTION_ICONS["superstar"][0],
             colour=Colour.gold(),
             title="Member achieved superstardom",
             thumbnail=member.avatar_url_as(static_format="png"),
@@ -196,7 +195,7 @@ class Superstarify(InfractionScheduler, Cog):
         """Remove the superstarify infraction and allow the user to change their nickname."""
         await self.pardon_infraction(ctx, "superstar", member)
 
-    async def _pardon_action(self, infraction: utils.Infraction) -> t.Optional[t.Dict[str, str]]:
+    async def _pardon_action(self, infraction: _utils.Infraction) -> t.Optional[t.Dict[str, str]]:
         """Pardon a superstar infraction and return a log dict."""
         if infraction["type"] != "superstar":
             return
@@ -213,11 +212,11 @@ class Superstarify(InfractionScheduler, Cog):
             return {}
 
         # DM the user about the expiration.
-        notified = await utils.notify_pardon(
+        notified = await _utils.notify_pardon(
             user=user,
             title="You are no longer superstarified",
             content="You may now change your nickname on the server.",
-            icon_url=utils.INFRACTION_ICONS["superstar"][1]
+            icon_url=_utils.INFRACTION_ICONS["superstar"][1]
         )
 
         return {
@@ -234,6 +233,11 @@ class Superstarify(InfractionScheduler, Cog):
         return rng.choice(STAR_NAMES)
 
     # This cannot be static (must have a __func__ attribute).
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators to invoke the commands in this cog."""
-        return with_role_check(ctx, *constants.MODERATION_ROLES)
+        return await has_any_role(*constants.MODERATION_ROLES).predicate(ctx)
+
+
+def setup(bot: Bot) -> None:
+    """Load the Superstarify cog."""
+    bot.add_cog(Superstarify(bot))
diff --git a/bot/cogs/moderation/modlog.py b/bot/exts/moderation/modlog.py
index 5f30d3744..b0d9b5b2b 100644
--- a/bot/cogs/moderation/modlog.py
+++ b/bot/exts/moderation/modlog.py
@@ -834,3 +834,8 @@ class ModLog(Cog, name="ModLog"):
             thumbnail=member.avatar_url_as(static_format="png"),
             channel_id=Channels.voice_log
         )
+
+
+def setup(bot: Bot) -> None:
+    """Load the ModLog cog."""
+    bot.add_cog(ModLog(bot))
diff --git a/bot/cogs/moderation/silence.py b/bot/exts/moderation/silence.py
index f8a6592bc..ac0c1c85e 100644
--- a/bot/cogs/moderation/silence.py
+++ b/bot/exts/moderation/silence.py
@@ -10,7 +10,6 @@ from discord.ext.commands import Context
 from bot.bot import Bot
 from bot.constants import Channels, Emojis, Guild, MODERATION_ROLES, Roles
 from bot.converters import HushDurationConverter
-from bot.utils.checks import with_role_check
 from bot.utils.scheduling import Scheduler
 
 log = logging.getLogger(__name__)
@@ -160,6 +159,11 @@ class Silence(commands.Cog):
             asyncio.create_task(self._mod_alerts_channel.send(message))
 
     # This cannot be static (must have a __func__ attribute).
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators to invoke the commands in this cog."""
-        return with_role_check(ctx, *MODERATION_ROLES)
+        return await commands.has_any_role(*MODERATION_ROLES).predicate(ctx)
+
+
+def setup(bot: Bot) -> None:
+    """Load the Silence cog."""
+    bot.add_cog(Silence(bot))
diff --git a/bot/cogs/moderation/slowmode.py b/bot/exts/moderation/slowmode.py
index 1d055afac..efd862aa5 100644
--- a/bot/cogs/moderation/slowmode.py
+++ b/bot/exts/moderation/slowmode.py
@@ -4,12 +4,11 @@ from typing import Optional
 
 from dateutil.relativedelta import relativedelta
 from discord import TextChannel
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.bot import Bot
 from bot.constants import Emojis, MODERATION_ROLES
 from bot.converters import DurationDelta
-from bot.decorators import with_role_check
 from bot.utils import time
 
 log = logging.getLogger(__name__)
@@ -87,9 +86,9 @@ class Slowmode(Cog):
             f'{Emojis.check_mark} The slowmode delay for {channel.mention} has been reset to 0 seconds.'
         )
 
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators to invoke the commands in this cog."""
-        return with_role_check(ctx, *MODERATION_ROLES)
+        return await has_any_role(*MODERATION_ROLES).predicate(ctx)
 
 
 def setup(bot: Bot) -> None:
diff --git a/bot/cogs/verification.py b/bot/exts/moderation/verification.py
index 9ae92a228..8ec68ac1e 100644
--- a/bot/cogs/verification.py
+++ b/bot/exts/moderation/verification.py
@@ -6,14 +6,14 @@ from datetime import datetime, timedelta
 
 import discord
 from discord.ext import tasks
-from discord.ext.commands import Cog, Context, command, group
+from discord.ext.commands import Cog, Context, command, group, has_any_role
 from discord.utils import snowflake_time
 
 from bot import constants
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
-from bot.decorators import in_whitelist, with_role, without_role
-from bot.utils.checks import InWhitelistCheckFailure, without_role_check
+from bot.decorators import has_no_roles, in_whitelist
+from bot.exts.moderation.modlog import ModLog
+from bot.utils.checks import InWhitelistCheckFailure, has_no_roles_check
 from bot.utils.redis_cache import RedisCache
 
 log = logging.getLogger(__name__)
@@ -568,7 +568,7 @@ class Verification(Cog):
     # endregion
     # region: task management commands
 
-    @with_role(*constants.MODERATION_ROLES)
+    @has_any_role(*constants.MODERATION_ROLES)
     @group(name="verification")
     async def verification_group(self, ctx: Context) -> None:
         """Manage internal verification tasks."""
@@ -653,7 +653,7 @@ class Verification(Cog):
         self.bot.stats.incr(f"verification.{category}")
 
     @command(name='accept', aliases=('verify', 'verified', 'accepted'), hidden=True)
-    @without_role(constants.Roles.verified)
+    @has_no_roles(constants.Roles.verified)
     @in_whitelist(channels=(constants.Channels.verification,))
     async def accept_command(self, ctx: Context, *_) -> None:  # We don't actually care about the args
         """Accept our rules and gain access to the rest of the server."""
@@ -736,9 +736,10 @@ class Verification(Cog):
             error.handled = True
 
     @staticmethod
-    def bot_check(ctx: Context) -> bool:
+    async def bot_check(ctx: Context) -> bool:
         """Block any command within the verification channel that is not !accept."""
-        if ctx.channel.id == constants.Channels.verification and without_role_check(ctx, *constants.MODERATION_ROLES):
+        is_verification = ctx.channel.id == constants.Channels.verification
+        if is_verification and await has_no_roles_check(ctx, *constants.MODERATION_ROLES):
             return ctx.command.name == "accept"
         else:
             return True
diff --git a/bot/exts/moderation/watchchannels/__init__.py b/bot/exts/moderation/watchchannels/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/bot/exts/moderation/watchchannels/__init__.py
diff --git a/bot/cogs/watchchannels/watchchannel.py b/bot/exts/moderation/watchchannels/_watchchannel.py
index a58b604c0..7118dee02 100644
--- a/bot/cogs/watchchannels/watchchannel.py
+++ b/bot/exts/moderation/watchchannels/_watchchannel.py
@@ -14,10 +14,10 @@ from discord.ext.commands import Cog, Context
 
 from bot.api import ResponseCodeError
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
-from bot.cogs.token_remover import TokenRemover
-from bot.cogs.webhook_remover import WEBHOOK_URL_RE
 from bot.constants import BigBrother as BigBrotherConfig, Guild as GuildConfig, Icons
+from bot.exts.filters.token_remover import TokenRemover
+from bot.exts.filters.webhook_remover import WEBHOOK_URL_RE
+from bot.exts.moderation.modlog import ModLog
 from bot.pagination import LinePaginator
 from bot.utils import CogABCMeta, messages
 from bot.utils.time import time_since
diff --git a/bot/cogs/watchchannels/bigbrother.py b/bot/exts/moderation/watchchannels/bigbrother.py
index 11ab8917a..3b44056d3 100644
--- a/bot/cogs/watchchannels/bigbrother.py
+++ b/bot/exts/moderation/watchchannels/bigbrother.py
@@ -2,14 +2,13 @@ import logging
 import textwrap
 from collections import ChainMap
 
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.bot import Bot
-from bot.cogs.moderation.utils import post_infraction
 from bot.constants import Channels, MODERATION_ROLES, Webhooks
 from bot.converters import FetchedMember
-from bot.decorators import with_role
-from .watchchannel import WatchChannel
+from bot.exts.moderation.infraction._utils import post_infraction
+from bot.exts.moderation.watchchannels._watchchannel import WatchChannel
 
 log = logging.getLogger(__name__)
 
@@ -28,13 +27,13 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         )
 
     @group(name='bigbrother', aliases=('bb',), invoke_without_command=True)
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def bigbrother_group(self, ctx: Context) -> None:
         """Monitors users by relaying their messages to the Big Brother watch channel."""
         await ctx.send_help(ctx.command)
 
     @bigbrother_group.command(name='watched', aliases=('all', 'list'))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def watched_command(
         self, ctx: Context, oldest_first: bool = False, update_cache: bool = True
     ) -> None:
@@ -49,7 +48,7 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         await self.list_watched_users(ctx, oldest_first=oldest_first, update_cache=update_cache)
 
     @bigbrother_group.command(name='oldest')
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def oldest_command(self, ctx: Context, update_cache: bool = True) -> None:
         """
         Shows Big Brother monitored users ordered by oldest watched.
@@ -60,7 +59,7 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         await ctx.invoke(self.watched_command, oldest_first=True, update_cache=update_cache)
 
     @bigbrother_group.command(name='watch', aliases=('w',), root_aliases=('watch',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def watch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """
         Relay messages sent by the given `user` to the `#big-brother` channel.
@@ -71,7 +70,7 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
         await self.apply_watch(ctx, user, reason)
 
     @bigbrother_group.command(name='unwatch', aliases=('uw',), root_aliases=('unwatch',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def unwatch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """Stop relaying messages by the given `user`."""
         await self.apply_unwatch(ctx, user, reason)
@@ -163,3 +162,8 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
             message = ":x: The specified user is currently not being watched."
 
         await ctx.send(message)
+
+
+def setup(bot: Bot) -> None:
+    """Load the BigBrother cog."""
+    bot.add_cog(BigBrother(bot))
diff --git a/bot/cogs/watchchannels/talentpool.py b/bot/exts/moderation/watchchannels/talentpool.py
index 76d6fe9bd..a77dbe156 100644
--- a/bot/cogs/watchchannels/talentpool.py
+++ b/bot/exts/moderation/watchchannels/talentpool.py
@@ -4,16 +4,15 @@ from collections import ChainMap
 from typing import Union
 
 from discord import Color, Embed, Member, User
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.api import ResponseCodeError
 from bot.bot import Bot
 from bot.constants import Channels, Guild, MODERATION_ROLES, STAFF_ROLES, Webhooks
 from bot.converters import FetchedMember
-from bot.decorators import with_role
+from bot.exts.moderation.watchchannels._watchchannel import WatchChannel
 from bot.pagination import LinePaginator
 from bot.utils import time
-from .watchchannel import WatchChannel
 
 log = logging.getLogger(__name__)
 
@@ -32,13 +31,13 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         )
 
     @group(name='talentpool', aliases=('tp', 'talent', 'nomination', 'n'), invoke_without_command=True)
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def nomination_group(self, ctx: Context) -> None:
         """Highlights the activity of helper nominees by relaying their messages to the talent pool channel."""
         await ctx.send_help(ctx.command)
 
     @nomination_group.command(name='watched', aliases=('all', 'list'), root_aliases=("nominees",))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def watched_command(
         self, ctx: Context, oldest_first: bool = False, update_cache: bool = True
     ) -> None:
@@ -53,7 +52,7 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         await self.list_watched_users(ctx, oldest_first=oldest_first, update_cache=update_cache)
 
     @nomination_group.command(name='oldest')
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def oldest_command(self, ctx: Context, update_cache: bool = True) -> None:
         """
         Shows talent pool monitored users ordered by oldest nomination.
@@ -64,7 +63,7 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         await ctx.invoke(self.watched_command, oldest_first=True, update_cache=update_cache)
 
     @nomination_group.command(name='watch', aliases=('w', 'add', 'a'), root_aliases=("nominate",))
-    @with_role(*STAFF_ROLES)
+    @has_any_role(*STAFF_ROLES)
     async def watch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """
         Relay messages sent by the given `user` to the `#talent-pool` channel.
@@ -129,7 +128,7 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         await ctx.send(msg)
 
     @nomination_group.command(name='history', aliases=('info', 'search'))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def history_command(self, ctx: Context, user: FetchedMember) -> None:
         """Shows the specified user's nomination history."""
         result = await self.bot.api_client.get(
@@ -158,7 +157,7 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
         )
 
     @nomination_group.command(name='unwatch', aliases=('end', ), root_aliases=("unnominate",))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def unwatch_command(self, ctx: Context, user: FetchedMember, *, reason: str) -> None:
         """
         Ends the active nomination of the specified user with the given reason.
@@ -171,13 +170,13 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
             await ctx.send(":x: The specified user does not have an active nomination")
 
     @nomination_group.group(name='edit', aliases=('e',), invoke_without_command=True)
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def nomination_edit_group(self, ctx: Context) -> None:
         """Commands to edit nominations."""
         await ctx.send_help(ctx.command)
 
     @nomination_edit_group.command(name='reason')
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def edit_reason_command(self, ctx: Context, nomination_id: int, *, reason: str) -> None:
         """
         Edits the reason/unnominate reason for the nomination with the given `id` depending on the status.
@@ -278,3 +277,8 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
             )
 
         return lines.strip()
+
+
+def setup(bot: Bot) -> None:
+    """Load the TalentPool cog."""
+    bot.add_cog(TalentPool(bot))
diff --git a/bot/exts/utils/__init__.py b/bot/exts/utils/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/bot/exts/utils/__init__.py
diff --git a/bot/cogs/bot.py b/bot/exts/utils/bot.py
index ddd1cef8d..7ed487d47 100644
--- a/bot/cogs/bot.py
+++ b/bot/exts/utils/bot.py
@@ -5,13 +5,12 @@ import time
 from typing import Optional, Tuple
 
 from discord import Embed, Message, RawMessageUpdateEvent, TextChannel
-from discord.ext.commands import Cog, Context, command, group
+from discord.ext.commands import Cog, Context, command, group, has_any_role
 
 from bot.bot import Bot
-from bot.cogs.token_remover import TokenRemover
-from bot.cogs.webhook_remover import WEBHOOK_URL_RE
 from bot.constants import Categories, Channels, DEBUG_MODE, Guild, MODERATION_ROLES, Roles, URLs
-from bot.decorators import with_role
+from bot.exts.filters.token_remover import TokenRemover
+from bot.exts.filters.webhook_remover import WEBHOOK_URL_RE
 from bot.utils.messages import wait_for_deletion
 
 log = logging.getLogger(__name__)
@@ -39,13 +38,13 @@ class BotCog(Cog, name="Bot"):
         self.codeblock_message_ids = {}
 
     @group(invoke_without_command=True, name="bot", hidden=True)
-    @with_role(Roles.verified)
+    @has_any_role(Roles.verified)
     async def botinfo_group(self, ctx: Context) -> None:
         """Bot informational commands."""
         await ctx.send_help(ctx.command)
 
     @botinfo_group.command(name='about', aliases=('info',), hidden=True)
-    @with_role(Roles.verified)
+    @has_any_role(Roles.verified)
     async def about_command(self, ctx: Context) -> None:
         """Get information about the bot."""
         embed = Embed(
@@ -63,7 +62,7 @@ class BotCog(Cog, name="Bot"):
         await ctx.send(embed=embed)
 
     @command(name='echo', aliases=('print',))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def echo_command(self, ctx: Context, channel: Optional[TextChannel], *, text: str) -> None:
         """Repeat the given message in either a specified channel or the current channel."""
         if channel is None:
@@ -72,7 +71,7 @@ class BotCog(Cog, name="Bot"):
             await channel.send(text)
 
     @command(name='embed')
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def embed_command(self, ctx: Context, channel: Optional[TextChannel], *, text: str) -> None:
         """Send the input within an embed to either a specified channel or the current channel."""
         embed = Embed(description=text)
diff --git a/bot/cogs/clean.py b/bot/exts/utils/clean.py
index f436e531a..236603dba 100644
--- a/bot/cogs/clean.py
+++ b/bot/exts/utils/clean.py
@@ -5,14 +5,13 @@ from typing import Iterable, Optional
 
 from discord import Colour, Embed, Message, TextChannel, User
 from discord.ext import commands
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.bot import Bot
-from bot.cogs.moderation import ModLog
 from bot.constants import (
     Channels, CleanMessages, Colours, Event, Icons, MODERATION_ROLES, NEGATIVE_REPLIES
 )
-from bot.decorators import with_role
+from bot.exts.moderation.modlog import ModLog
 
 log = logging.getLogger(__name__)
 
@@ -192,13 +191,13 @@ class Clean(Cog):
         )
 
     @group(invoke_without_command=True, name="clean", aliases=["purge"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_group(self, ctx: Context) -> None:
         """Commands for cleaning messages in channels."""
         await ctx.send_help(ctx.command)
 
     @clean_group.command(name="user", aliases=["users"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_user(
         self,
         ctx: Context,
@@ -210,7 +209,7 @@ class Clean(Cog):
         await self._clean_messages(amount, ctx, user=user, channels=channels)
 
     @clean_group.command(name="all", aliases=["everything"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_all(
         self,
         ctx: Context,
@@ -221,7 +220,7 @@ class Clean(Cog):
         await self._clean_messages(amount, ctx, channels=channels)
 
     @clean_group.command(name="bots", aliases=["bot"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_bots(
         self,
         ctx: Context,
@@ -232,7 +231,7 @@ class Clean(Cog):
         await self._clean_messages(amount, ctx, bots_only=True, channels=channels)
 
     @clean_group.command(name="regex", aliases=["word", "expression"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_regex(
         self,
         ctx: Context,
@@ -244,7 +243,7 @@ class Clean(Cog):
         await self._clean_messages(amount, ctx, regex=regex, channels=channels)
 
     @clean_group.command(name="message", aliases=["messages"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_message(self, ctx: Context, message: Message) -> None:
         """Delete all messages until certain message, stop cleaning after hitting the `message`."""
         await self._clean_messages(
@@ -255,7 +254,7 @@ class Clean(Cog):
         )
 
     @clean_group.command(name="stop", aliases=["cancel", "abort"])
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def clean_cancel(self, ctx: Context) -> None:
         """If there is an ongoing cleaning process, attempt to immediately cancel it."""
         self.cleaning = False
diff --git a/bot/cogs/eval.py b/bot/exts/utils/eval.py
index 23e5998d8..6419b320e 100644
--- a/bot/cogs/eval.py
+++ b/bot/exts/utils/eval.py
@@ -9,11 +9,10 @@ from io import StringIO
 from typing import Any, Optional, Tuple
 
 import discord
-from discord.ext.commands import Cog, Context, group
+from discord.ext.commands import Cog, Context, group, has_any_role
 
 from bot.bot import Bot
 from bot.constants import Roles
-from bot.decorators import with_role
 from bot.interpreter import Interpreter
 from bot.utils import find_nth_occurrence, send_to_paste_service
 
@@ -199,14 +198,14 @@ async def func():  # (None,) -> Any
         await ctx.send(f"```py\n{out}```", embed=embed)
 
     @group(name='internal', aliases=('int',))
-    @with_role(Roles.owners, Roles.admins)
+    @has_any_role(Roles.owners, Roles.admins)
     async def internal_group(self, ctx: Context) -> None:
         """Internal commands. Top secret!"""
         if not ctx.invoked_subcommand:
             await ctx.send_help(ctx.command)
 
     @internal_group.command(name='eval', aliases=('e',))
-    @with_role(Roles.admins, Roles.owners)
+    @has_any_role(Roles.admins, Roles.owners)
     async def eval(self, ctx: Context, *, code: str) -> None:
         """Run eval in a REPL-like format."""
         code = code.strip("`")
diff --git a/bot/cogs/extensions.py b/bot/exts/utils/extensions.py
index 396e406b0..418db0150 100644
--- a/bot/cogs/extensions.py
+++ b/bot/exts/utils/extensions.py
@@ -2,25 +2,22 @@ import functools
 import logging
 import typing as t
 from enum import Enum
-from pkgutil import iter_modules
 
 from discord import Colour, Embed
 from discord.ext import commands
 from discord.ext.commands import Context, group
 
+from bot import exts
 from bot.bot import Bot
 from bot.constants import Emojis, MODERATION_ROLES, Roles, URLs
 from bot.pagination import LinePaginator
-from bot.utils.checks import with_role_check
+from bot.utils.extensions import EXTENSIONS, unqualify
 
 log = logging.getLogger(__name__)
 
-UNLOAD_BLACKLIST = {"bot.cogs.extensions", "bot.cogs.modlog"}
-EXTENSIONS = frozenset(
-    ext.name
-    for ext in iter_modules(("bot/cogs",), "bot.cogs.")
-    if ext.name[-1] != "_"
-)
+
+UNLOAD_BLACKLIST = {f"{exts.__name__}.utils.extensions", f"{exts.__name__}.moderation.modlog"}
+BASE_PATH_LEN = len(exts.__name__.split("."))
 
 
 class Action(Enum):
@@ -47,11 +44,25 @@ class Extension(commands.Converter):
 
         argument = argument.lower()
 
-        if "." not in argument:
-            argument = f"bot.cogs.{argument}"
-
         if argument in EXTENSIONS:
             return argument
+        elif (qualified_arg := f"{exts.__name__}.{argument}") in EXTENSIONS:
+            return qualified_arg
+
+        matches = []
+        for ext in EXTENSIONS:
+            if argument == unqualify(ext):
+                matches.append(ext)
+
+        if len(matches) > 1:
+            matches.sort()
+            names = "\n".join(matches)
+            raise commands.BadArgument(
+                f":x: `{argument}` is an ambiguous extension name. "
+                f"Please use one of the following fully-qualified names.```\n{names}```"
+            )
+        elif matches:
+            return matches[0]
         else:
             raise commands.BadArgument(f":x: Could not find the extension `{argument}`.")
 
@@ -139,27 +150,44 @@ class Extensions(commands.Cog):
         Grey indicates that the extension is unloaded.
         Green indicates that the extension is currently loaded.
         """
-        embed = Embed()
-        lines = []
-
-        embed.colour = Colour.blurple()
+        embed = Embed(colour=Colour.blurple())
         embed.set_author(
             name="Extensions List",
             url=URLs.github_bot_repo,
             icon_url=URLs.bot_avatar
         )
 
-        for ext in sorted(list(EXTENSIONS)):
+        lines = []
+        categories = self.group_extension_statuses()
+        for category, extensions in sorted(categories.items()):
+            # Treat each category as a single line by concatenating everything.
+            # This ensures the paginator will not cut off a page in the middle of a category.
+            category = category.replace("_", " ").title()
+            extensions = "\n".join(sorted(extensions))
+            lines.append(f"**{category}**\n{extensions}\n")
+
+        log.debug(f"{ctx.author} requested a list of all cogs. Returning a paginated list.")
+        await LinePaginator.paginate(lines, ctx, embed, scale_to_size=700, empty=False)
+
+    def group_extension_statuses(self) -> t.Mapping[str, str]:
+        """Return a mapping of extension names and statuses to their categories."""
+        categories = {}
+
+        for ext in EXTENSIONS:
             if ext in self.bot.extensions:
                 status = Emojis.status_online
             else:
                 status = Emojis.status_offline
 
-            ext = ext.rsplit(".", 1)[1]
-            lines.append(f"{status}  {ext}")
+            path = ext.split(".")
+            if len(path) > BASE_PATH_LEN + 1:
+                category = " - ".join(path[BASE_PATH_LEN:-1])
+            else:
+                category = "uncategorised"
 
-        log.debug(f"{ctx.author} requested a list of all cogs. Returning a paginated list.")
-        await LinePaginator.paginate(lines, ctx, embed, max_size=300, empty=False)
+            categories.setdefault(category, []).append(f"{status}  {path[-1]}")
+
+        return categories
 
     def batch_manage(self, action: Action, *extensions: str) -> str:
         """
@@ -219,9 +247,9 @@ class Extensions(commands.Cog):
         return msg, error_msg
 
     # This cannot be static (must have a __func__ attribute).
-    def cog_check(self, ctx: Context) -> bool:
+    async def cog_check(self, ctx: Context) -> bool:
         """Only allow moderators and core developers to invoke the commands in this cog."""
-        return with_role_check(ctx, *MODERATION_ROLES, Roles.core_developers)
+        return await commands.has_any_role(*MODERATION_ROLES, Roles.core_developers).predicate(ctx)
 
     # This cannot be static (must have a __func__ attribute).
     async def cog_command_error(self, ctx: Context, error: Exception) -> None:
diff --git a/bot/cogs/jams.py b/bot/exts/utils/jams.py
index b3102db2f..1c0988343 100644
--- a/bot/cogs/jams.py
+++ b/bot/exts/utils/jams.py
@@ -7,7 +7,6 @@ from more_itertools import unique_everseen
 
 from bot.bot import Bot
 from bot.constants import Roles
-from bot.decorators import with_role
 
 log = logging.getLogger(__name__)
 
@@ -22,7 +21,7 @@ class CodeJams(commands.Cog):
         self.bot = bot
 
     @commands.command()
-    @with_role(Roles.admins)
+    @commands.has_any_role(Roles.admins)
     async def createteam(self, ctx: commands.Context, team_name: str, members: commands.Greedy[Member]) -> None:
         """
         Create team channels (voice and text) in the Code Jams category, assign roles, and add overwrites for the team.
diff --git a/bot/cogs/reminders.py b/bot/exts/utils/reminders.py
index 08bce2153..6806f2889 100644
--- a/bot/cogs/reminders.py
+++ b/bot/exts/utils/reminders.py
@@ -15,7 +15,7 @@ from bot.bot import Bot
 from bot.constants import Guild, Icons, MODERATION_ROLES, POSITIVE_REPLIES, Roles, STAFF_ROLES
 from bot.converters import Duration
 from bot.pagination import LinePaginator
-from bot.utils.checks import with_role_check, without_role_check
+from bot.utils.checks import has_any_role_check, has_no_roles_check
 from bot.utils.messages import send_denial
 from bot.utils.scheduling import Scheduler
 from bot.utils.time import humanize_delta
@@ -117,9 +117,9 @@ class Reminders(Cog):
 
         If mentions aren't allowed, also return the type of mention(s) disallowed.
         """
-        if without_role_check(ctx, *STAFF_ROLES):
+        if await has_no_roles_check(ctx, *STAFF_ROLES):
             return False, "members/roles"
-        elif without_role_check(ctx, *MODERATION_ROLES):
+        elif await has_no_roles_check(ctx, *MODERATION_ROLES):
             return all(isinstance(mention, discord.Member) for mention in mentions), "roles"
         else:
             return True, ""
@@ -240,7 +240,7 @@ class Reminders(Cog):
         Expiration is parsed per: http://strftime.org/
         """
         # If the user is not staff, we need to verify whether or not to make a reminder at all.
-        if without_role_check(ctx, *STAFF_ROLES):
+        if await has_no_roles_check(ctx, *STAFF_ROLES):
 
             # If they don't have permission to set a reminder in this channel
             if ctx.channel.id not in WHITELISTED_CHANNELS:
@@ -431,7 +431,7 @@ class Reminders(Cog):
 
         The check passes when the user is an admin, or if they created the reminder.
         """
-        if with_role_check(ctx, Roles.admins):
+        if await has_any_role_check(ctx, Roles.admins):
             return True
 
         api_response = await self.bot.api_client.get(f"bot/reminders/{reminder_id}")
diff --git a/bot/cogs/snekbox.py b/bot/exts/utils/snekbox.py
index 03bf454ac..b3baffba2 100644
--- a/bot/cogs/snekbox.py
+++ b/bot/exts/utils/snekbox.py
@@ -150,6 +150,7 @@ class Snekbox(Cog):
             output = output.replace("<!@", "<!@\u200B")  # Zero-width space
 
         if ESCAPE_REGEX.findall(output):
+            paste_link = await self.upload_output(original_output)
             return "Code block escape attempt detected; will not output result", paste_link
 
         truncated = False
diff --git a/bot/cogs/utils.py b/bot/exts/utils/utils.py
index d96abbd5a..6b6941064 100644
--- a/bot/cogs/utils.py
+++ b/bot/exts/utils/utils.py
@@ -7,11 +7,11 @@ from io import StringIO
 from typing import Tuple, Union
 
 from discord import Colour, Embed, utils
-from discord.ext.commands import BadArgument, Cog, Context, clean_content, command
+from discord.ext.commands import BadArgument, Cog, Context, clean_content, command, has_any_role
 
 from bot.bot import Bot
 from bot.constants import Channels, MODERATION_ROLES, STAFF_ROLES
-from bot.decorators import in_whitelist, with_role
+from bot.decorators import in_whitelist
 from bot.pagination import LinePaginator
 from bot.utils import messages
 
@@ -224,7 +224,7 @@ class Utils(Cog):
         await ctx.send(embed=embed)
 
     @command(aliases=("poll",))
-    @with_role(*MODERATION_ROLES)
+    @has_any_role(*MODERATION_ROLES)
     async def vote(self, ctx: Context, title: clean_content(fix_channel_mentions=True), *options: str) -> None:
         """
         Build a quick voting poll with matching reactions with the provided options.
diff --git a/bot/rules/__init__.py b/bot/rules/__init__.py
index 8a69cadee..a01ceae73 100644
--- a/bot/rules/__init__.py
+++ b/bot/rules/__init__.py
@@ -10,4 +10,3 @@ from .links import apply as apply_links
 from .mentions import apply as apply_mentions
 from .newlines import apply as apply_newlines
 from .role_mentions import apply as apply_role_mentions
-from .everyone_ping import apply as apply_everyone_ping
diff --git a/bot/rules/everyone_ping.py b/bot/rules/everyone_ping.py
deleted file mode 100644
index 89d9fe570..000000000
--- a/bot/rules/everyone_ping.py
+++ /dev/null
@@ -1,41 +0,0 @@
-import random
-import re
-from typing import Dict, Iterable, List, Optional, Tuple
-
-from discord import Embed, Member, Message
-
-from bot.constants import Colours, Guild, NEGATIVE_REPLIES
-
-# Generate regex for checking for pings:
-guild_id = Guild.id
-EVERYONE_RE_INLINE_CODE = re.compile(rf"^(?!`).*@everyone.*(?!`)$|^(?!`).*<@&{guild_id}>.*(?!`)$")
-EVERYONE_RE_MULTILINE_CODE = re.compile(rf"^(?!```).*@everyone.*(?!```)$|^(?!```).*<@&{guild_id}>.*(?!```)$")
-
-
-async def apply(
-    last_message: Message,
-    recent_messages: List[Message],
-    config: Dict[str, int],
-) -> Optional[Tuple[str, Iterable[Member], Iterable[Message]]]:
-    """Detects if a user has sent an '@everyone' ping."""
-    relevant_messages = tuple(msg for msg in recent_messages if msg.author == last_message.author)
-
-    everyone_messages_count = 0
-    for msg in relevant_messages:
-        num_everyone_pings_inline = len(re.findall(EVERYONE_RE_INLINE_CODE, msg.content))
-        num_everyone_pings_multiline = len(re.findall(EVERYONE_RE_MULTILINE_CODE, msg.content))
-        if num_everyone_pings_inline and num_everyone_pings_multiline:
-            everyone_messages_count += 1
-
-    if everyone_messages_count > config["max"]:
-        # Send the channel an embed giving the user more info:
-        embed_text = f"Please don't try to ping {last_message.guild.member_count:,} people."
-        embed = Embed(title=random.choice(NEGATIVE_REPLIES), description=embed_text, colour=Colours.soft_red)
-        await last_message.channel.send(embed=embed)
-
-        return (
-            "pinged the everyone role",
-            (last_message.author,),
-            relevant_messages,
-        )
-    return None
diff --git a/bot/utils/checks.py b/bot/utils/checks.py
index f0ef36302..460a937d8 100644
--- a/bot/utils/checks.py
+++ b/bot/utils/checks.py
@@ -1,6 +1,6 @@
 import datetime
 import logging
-from typing import Callable, Container, Iterable, Optional
+from typing import Callable, Container, Iterable, Optional, Union
 
 from discord.ext.commands import (
     BucketType,
@@ -11,6 +11,8 @@ from discord.ext.commands import (
     Context,
     Cooldown,
     CooldownMapping,
+    NoPrivateMessage,
+    has_any_role,
 )
 
 from bot import constants
@@ -89,35 +91,32 @@ def in_whitelist_check(
     return False
 
 
-def with_role_check(ctx: Context, *role_ids: int) -> bool:
-    """Returns True if the user has any one of the roles in role_ids."""
-    if not ctx.guild:  # Return False in a DM
-        log.trace(f"{ctx.author} tried to use the '{ctx.command.name}'command from a DM. "
-                  "This command is restricted by the with_role decorator. Rejecting request.")
-        return False
+async def has_any_role_check(ctx: Context, *roles: Union[str, int]) -> bool:
+    """
+    Returns True if the context's author has any of the specified roles.
 
-    for role in ctx.author.roles:
-        if role.id in role_ids:
-            log.trace(f"{ctx.author} has the '{role.name}' role, and passes the check.")
-            return True
+    `roles` are the names or IDs of the roles for which to check.
+    False is always returns if the context is outside a guild.
+    """
+    try:
+        return await has_any_role(*roles).predicate(ctx)
+    except CheckFailure:
+        return False
 
-    log.trace(f"{ctx.author} does not have the required role to use "
-              f"the '{ctx.command.name}' command, so the request is rejected.")
-    return False
 
+async def has_no_roles_check(ctx: Context, *roles: Union[str, int]) -> bool:
+    """
+    Returns True if the context's author doesn't have any of the specified roles.
 
-def without_role_check(ctx: Context, *role_ids: int) -> bool:
-    """Returns True if the user does not have any of the roles in role_ids."""
-    if not ctx.guild:  # Return False in a DM
-        log.trace(f"{ctx.author} tried to use the '{ctx.command.name}' command from a DM. "
-                  "This command is restricted by the without_role decorator. Rejecting request.")
+    `roles` are the names or IDs of the roles for which to check.
+    False is always returns if the context is outside a guild.
+    """
+    try:
+        return not await has_any_role(*roles).predicate(ctx)
+    except NoPrivateMessage:
         return False
-
-    author_roles = [role.id for role in ctx.author.roles]
-    check = all(role not in author_roles for role in role_ids)
-    log.trace(f"{ctx.author} tried to call the '{ctx.command.name}' command. "
-              f"The result of the without_role check was {check}.")
-    return check
+    except CheckFailure:
+        return True
 
 
 def cooldown_with_role_bypass(rate: int, per: float, type: BucketType = BucketType.default, *,
diff --git a/bot/utils/extensions.py b/bot/utils/extensions.py
new file mode 100644
index 000000000..50350ea8d
--- /dev/null
+++ b/bot/utils/extensions.py
@@ -0,0 +1,34 @@
+import importlib
+import inspect
+import pkgutil
+from typing import Iterator, NoReturn
+
+from bot import exts
+
+
+def unqualify(name: str) -> str:
+    """Return an unqualified name given a qualified module/package `name`."""
+    return name.rsplit(".", maxsplit=1)[-1]
+
+
+def walk_extensions() -> Iterator[str]:
+    """Yield extension names from the bot.exts subpackage."""
+
+    def on_error(name: str) -> NoReturn:
+        raise ImportError(name=name)  # pragma: no cover
+
+    for module in pkgutil.walk_packages(exts.__path__, f"{exts.__name__}.", onerror=on_error):
+        if unqualify(module.name).startswith("_"):
+            # Ignore module/package names starting with an underscore.
+            continue
+
+        if module.ispkg:
+            imported = importlib.import_module(module.name)
+            if not inspect.isfunction(getattr(imported, "setup", None)):
+                # If it lacks a setup function, it's not an extension.
+                continue
+
+        yield module.name
+
+
+EXTENSIONS = frozenset(walk_extensions())
diff --git a/config-default.yml b/config-default.yml
index fe15e5a87..c809a7340 100644
--- a/config-default.yml
+++ b/config-default.yml
@@ -271,17 +271,19 @@ guild:
 
 filter:
     # What do we filter?
-    filter_zalgo:       false
-    filter_invites:     true
-    filter_domains:     true
-    watch_regex:        true
-    watch_rich_embeds:  true
+    filter_zalgo:          false
+    filter_invites:        true
+    filter_domains:        true
+    filter_everyone_ping:  true
+    watch_regex:           true
+    watch_rich_embeds:     true
 
     # Notify user on filter?
     # Notifications are not expected for "watchlist" type filters
-    notify_user_zalgo:       false
-    notify_user_invites:     true
-    notify_user_domains:     false
+    notify_user_zalgo:          false
+    notify_user_invites:        true
+    notify_user_domains:        false
+    notify_user_everyone_ping:  true
 
     # Filter configuration
     ping_everyone:             true
@@ -387,12 +389,6 @@ anti_spam:
             interval: 10
             max: 3
 
-        # The everyone ping filter is temporarily disabled
-        # until we've fixed a couple of bugs.
-        # everyone_ping:
-        #    interval: 10
-        #    max: 0
-
 
 reddit:
     subreddits:
diff --git a/tests/bot/exts/__init__.py b/tests/bot/exts/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/__init__.py
diff --git a/tests/bot/exts/backend/__init__.py b/tests/bot/exts/backend/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ b/tests/bot/exts/backend/__init__.py
diff --git a/tests/bot/exts/backend/sync/__init__.py b/tests/bot/exts/backend/sync/__init__.py
new file mode 100644
index 000000000..e69de29bb
--- /dev/null
+++ 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 f50c0492d..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
 
 
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 3349caa73..a0ff8a877 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 tests.helpers import MockBot, MockMessage, autospec
 
 
@@ -132,7 +132,7 @@ 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 = ()
@@ -143,8 +143,8 @@ 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 = [
@@ -167,8 +167,8 @@ 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)]
@@ -230,7 +230,7 @@ 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 77b0ddf17..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'
 
@@ -339,8 +339,8 @@ class UserInfractionHelperMethodTests(unittest.TestCase):
         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."""
 
@@ -515,7 +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."""
 
@@ -554,7 +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]
@@ -567,7 +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]
@@ -580,7 +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]
@@ -593,7 +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 30a04422a..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)
 
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 f22952931..40b2202aa 100644
--- a/tests/bot/cogs/test_snekbox.py
+++ b/tests/bot/exts/utils/test_snekbox.py
@@ -5,8 +5,8 @@ from unittest.mock import AsyncMock, MagicMock, Mock, call, create_autospec, pat
 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
 
 
@@ -38,7 +38,7 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
         result = await self.cog.upload_output("-" * (snekbox.MAX_PASTE_LEN + 1))
         self.assertEqual(result, "too long to upload")
 
-    @patch("bot.cogs.snekbox.send_to_paste_service")
+    @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."""
         await self.cog.upload_output("Test output.")
@@ -69,14 +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(
@@ -117,12 +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'),
@@ -266,7 +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/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."""