Merge branch 'master' into bug/980/fuzzy-processing

19 files changed, 427 insertions, 177 deletions

diff --git a/bot/__main__.py b/bot/__main__.py
index 37e62c2f1..49388455a 100644
--- a/bot/__main__.py
+++ b/bot/__main__.py
@@ -54,6 +54,7 @@ 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.information")
diff --git a/bot/cogs/dm_relay.py b/bot/cogs/dm_relay.py
new file mode 100644
index 000000000..0dc15d4b1
--- /dev/null
+++ b/bot/cogs/dm_relay.py
@@ -0,0 +1,124 @@
+import logging
+from typing import Optional
+
+import discord
+from discord import Color
+from discord.ext import commands
+from discord.ext.commands import Cog
+
+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.messages import send_attachments
+from bot.utils.webhooks import send_webhook
+
+log = logging.getLogger(__name__)
+
+
+class DMRelay(Cog):
+    """Relay direct messages to and from the bot."""
+
+    # RedisCache[str, t.Union[discord.User.id, discord.Member.id]]
+    dm_cache = RedisCache()
+
+    def __init__(self, bot: Bot):
+        self.bot = bot
+        self.webhook_id = constants.Webhooks.dm_log
+        self.webhook = None
+        self.bot.loop.create_task(self.fetch_webhook())
+
+    @commands.command(aliases=("reply",))
+    async def send_dm(self, ctx: commands.Context, member: Optional[UserMentionOrID], *, message: str) -> None:
+        """
+        Allows you to send a DM to a user from the bot.
+
+        If `member` is not provided, it will send to the last user who DM'd the bot.
+
+        This feature should be used extremely sparingly. Use ModMail if you need to have a serious
+        conversation with a user. This is just for responding to extraordinary DMs, having a little
+        fun with users, and telling people they are DMing the wrong bot.
+
+        NOTE: This feature will be removed if it is overused.
+        """
+        if not member:
+            user_id = await self.dm_cache.get("last_user")
+            member = ctx.guild.get_member(user_id) if user_id else None
+
+        # If we still don't have a Member at this point, give up
+        if not member:
+            log.debug("This bot has never gotten a DM, or the RedisCache has been cleared.")
+            await ctx.message.add_reaction("❌")
+            return
+
+        try:
+            await member.send(message)
+        except discord.errors.Forbidden:
+            log.debug("User has disabled DMs.")
+            await ctx.message.add_reaction("❌")
+        else:
+            await ctx.message.add_reaction("✅")
+            self.bot.stats.incr("dm_relay.dm_sent")
+
+    async def fetch_webhook(self) -> None:
+        """Fetches the webhook object, so we can post to it."""
+        await self.bot.wait_until_guild_available()
+
+        try:
+            self.webhook = await self.bot.fetch_webhook(self.webhook_id)
+        except discord.HTTPException:
+            log.exception(f"Failed to fetch webhook with id `{self.webhook_id}`")
+
+    @Cog.listener()
+    async def on_message(self, message: discord.Message) -> None:
+        """Relays the message's content and attachments to the dm_log channel."""
+        # Only relay DMs from humans
+        if message.author.bot or message.guild or self.webhook is None:
+            return
+
+        if message.clean_content:
+            await send_webhook(
+                webhook=self.webhook,
+                content=message.clean_content,
+                username=f"{message.author.display_name} ({message.author.id})",
+                avatar_url=message.author.avatar_url
+            )
+            await self.dm_cache.set("last_user", message.author.id)
+            self.bot.stats.incr("dm_relay.dm_received")
+
+        # Handle any attachments
+        if message.attachments:
+            try:
+                await send_attachments(message, self.webhook)
+            except (discord.errors.Forbidden, discord.errors.NotFound):
+                e = discord.Embed(
+                    description=":x: **This message contained an attachment, but it could not be retrieved**",
+                    color=Color.red()
+                )
+                await send_webhook(
+                    webhook=self.webhook,
+                    embed=e,
+                    username=message.author.display_name,
+                    avatar_url=message.author.avatar_url
+                )
+            except discord.HTTPException:
+                log.exception("Failed to send an attachment to the webhook")
+
+    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),
+            in_whitelist_check(
+                ctx,
+                channels=[constants.Channels.dm_log],
+                redirect=None,
+                fail_silently=True,
+            )
+        ]
+        return all(checks)
+
+
+def setup(bot: Bot) -> None:
+    """Load the DMRelay  cog."""
+    bot.add_cog(DMRelay(bot))
diff --git a/bot/cogs/duck_pond.py b/bot/cogs/duck_pond.py
index 5b6a7fd62..7021069fa 100644
--- a/bot/cogs/duck_pond.py
+++ b/bot/cogs/duck_pond.py
@@ -1,5 +1,5 @@
 import logging
-from typing import Optional, Union
+from typing import Union
 
 import discord
 from discord import Color, Embed, Member, Message, RawReactionActionEvent, User, errors
@@ -7,7 +7,8 @@ from discord.ext.commands import Cog
 
 from bot import constants
 from bot.bot import Bot
-from bot.utils.messages import send_attachments, sub_clyde
+from bot.utils.messages import send_attachments
+from bot.utils.webhooks import send_webhook
 
 log = logging.getLogger(__name__)
 
@@ -18,6 +19,7 @@ class DuckPond(Cog):
     def __init__(self, bot: Bot):
         self.bot = bot
         self.webhook_id = constants.Webhooks.duck_pond
+        self.webhook = None
         self.bot.loop.create_task(self.fetch_webhook())
 
     async def fetch_webhook(self) -> None:
@@ -47,24 +49,6 @@ class DuckPond(Cog):
                         return True
         return False
 
-    async def send_webhook(
-        self,
-        content: Optional[str] = None,
-        username: Optional[str] = None,
-        avatar_url: Optional[str] = None,
-        embed: Optional[Embed] = None,
-    ) -> None:
-        """Send a webhook to the duck_pond channel."""
-        try:
-            await self.webhook.send(
-                content=content,
-                username=sub_clyde(username),
-                avatar_url=avatar_url,
-                embed=embed
-            )
-        except discord.HTTPException:
-            log.exception("Failed to send a message to the Duck Pool webhook")
-
     async def count_ducks(self, message: Message) -> int:
         """
         Count the number of ducks in the reactions of a specific message.
@@ -94,10 +78,9 @@ class DuckPond(Cog):
 
     async def relay_message(self, message: Message) -> None:
         """Relays the message's content and attachments to the duck pond channel."""
-        clean_content = message.clean_content
-
-        if clean_content:
-            await self.send_webhook(
+        if message.clean_content:
+            await send_webhook(
+                webhook=self.webhook,
                 content=message.clean_content,
                 username=message.author.display_name,
                 avatar_url=message.author.avatar_url
@@ -111,7 +94,8 @@ class DuckPond(Cog):
                     description=":x: **This message contained an attachment, but it could not be retrieved**",
                     color=Color.red()
                 )
-                await self.send_webhook(
+                await send_webhook(
+                    webhook=self.webhook,
                     embed=e,
                     username=message.author.display_name,
                     avatar_url=message.author.avatar_url
diff --git a/bot/cogs/error_handler.py b/bot/cogs/error_handler.py
index 5de961116..233851e41 100644
--- a/bot/cogs/error_handler.py
+++ b/bot/cogs/error_handler.py
@@ -170,7 +170,7 @@ class ErrorHandler(Cog):
             await prepared_help_command
             self.bot.stats.incr("errors.too_many_arguments")
         elif isinstance(e, errors.BadArgument):
-            await ctx.send(f"Bad argument: {e}\n")
+            await ctx.send("Bad argument: Please double-check your input arguments and try again.\n")
             await prepared_help_command
             self.bot.stats.incr("errors.bad_argument")
         elif isinstance(e, errors.BadUnionArgument):
diff --git a/bot/cogs/filtering.py b/bot/cogs/filtering.py
index 099606b82..bd665f424 100644
--- a/bot/cogs/filtering.py
+++ b/bot/cogs/filtering.py
@@ -2,7 +2,7 @@ import asyncio
 import logging
 import re
 from datetime import datetime, timedelta
-from typing import List, Mapping, Optional, Union
+from typing import List, Mapping, Optional, Tuple, Union
 
 import dateutil
 import discord.errors
@@ -198,24 +198,67 @@ class Filtering(Cog):
             # Update time when alert sent
             await self.name_alerts.set(member.id, datetime.utcnow().timestamp())
 
-    async def _filter_message(self, msg: Message, delta: Optional[int] = None) -> None:
-        """Filter the input message to see if it violates any of our rules, and then respond accordingly."""
+    async def filter_eval(self, result: str, msg: Message) -> bool:
+        """
+        Filter the result of an !eval to see if it violates any of our rules, and then respond accordingly.
+
+        Also requires the original message, to check whether to filter and for mod logs.
+        Returns whether a filter was triggered or not.
+        """
+        filter_triggered = False
         # Should we filter this message?
-        role_whitelisted = False
+        if self._check_filter(msg):
+            for filter_name, _filter in self.filters.items():
+                # Is this specific filter enabled in the config?
+                # We also do not need to worry about filters that take the full message,
+                # since all we have is an arbitrary string.
+                if _filter["enabled"] and _filter["content_only"]:
+                    match = await _filter["function"](result)
 
-        if type(msg.author) is Member:  # Only Member has roles, not User.
-            for role in msg.author.roles:
-                if role.id in Filter.role_whitelist:
-                    role_whitelisted = True
+                    if match:
+                        # If this is a filter (not a watchlist), we set the variable so we know
+                        # that it has been triggered
+                        if _filter["type"] == "filter":
+                            filter_triggered = True
 
-        filter_message = (
-            msg.channel.id not in Filter.channel_whitelist  # Channel not in whitelist
-            and not role_whitelisted                        # Role not in whitelist
-            and not msg.author.bot                          # Author not a bot
-        )
+                        # We do not have to check against DM channels since !eval cannot be used there.
+                        channel_str = f"in {msg.channel.mention}"
+
+                        message_content, additional_embeds, additional_embeds_msg = self._add_stats(
+                            filter_name, match, result
+                        )
+
+                        message = (
+                            f"The {filter_name} {_filter['type']} was triggered "
+                            f"by **{msg.author}** "
+                            f"(`{msg.author.id}`) {channel_str} using !eval with "
+                            f"[the following message]({msg.jump_url}):\n\n"
+                            f"{message_content}"
+                        )
+
+                        log.debug(message)
 
-        # If none of the above, we can start filtering.
-        if filter_message:
+                        # Send pretty mod log embed to mod-alerts
+                        await self.mod_log.send_log_message(
+                            icon_url=Icons.filtering,
+                            colour=Colour(Colours.soft_red),
+                            title=f"{_filter['type'].title()} triggered!",
+                            text=message,
+                            thumbnail=msg.author.avatar_url_as(static_format="png"),
+                            channel_id=Channels.mod_alerts,
+                            ping_everyone=Filter.ping_everyone,
+                            additional_embeds=additional_embeds,
+                            additional_embeds_msg=additional_embeds_msg
+                        )
+
+                        break  # We don't want multiple filters to trigger
+
+        return filter_triggered
+
+    async def _filter_message(self, msg: Message, delta: Optional[int] = None) -> None:
+        """Filter the input message to see if it violates any of our rules, and then respond accordingly."""
+        # Should we filter this message?
+        if self._check_filter(msg):
             for filter_name, _filter in self.filters.items():
                 # Is this specific filter enabled in the config?
                 if _filter["enabled"]:
@@ -274,16 +317,9 @@ class Filtering(Cog):
                         else:
                             channel_str = f"in {msg.channel.mention}"
 
-                        # Word and match stats for watch_regex
-                        if filter_name == "watch_regex":
-                            surroundings = match.string[max(match.start() - 10, 0): match.end() + 10]
-                            message_content = (
-                                f"**Match:** '{match[0]}'\n"
-                                f"**Location:** '...{escape_markdown(surroundings)}...'\n"
-                                f"\n**Original Message:**\n{escape_markdown(msg.content)}"
-                            )
-                        else:  # Use content of discord Message
-                            message_content = msg.content
+                        message_content, additional_embeds, additional_embeds_msg = self._add_stats(
+                            filter_name, match, msg.content
+                        )
 
                         message = (
                             f"The {filter_name} {_filter['type']} was triggered "
@@ -295,30 +331,6 @@ class Filtering(Cog):
 
                         log.debug(message)
 
-                        self.bot.stats.incr(f"filters.{filter_name}")
-
-                        additional_embeds = None
-                        additional_embeds_msg = None
-
-                        # The function returns True for invalid invites.
-                        # They have no data so additional embeds can't be created for them.
-                        if filter_name == "filter_invites" and match is not True:
-                            additional_embeds = []
-                            for invite, data in match.items():
-                                embed = discord.Embed(description=(
-                                    f"**Members:**\n{data['members']}\n"
-                                    f"**Active:**\n{data['active']}"
-                                ))
-                                embed.set_author(name=data["name"])
-                                embed.set_thumbnail(url=data["icon"])
-                                embed.set_footer(text=f"Guild Invite Code: {invite}")
-                                additional_embeds.append(embed)
-                            additional_embeds_msg = "For the following guild(s):"
-
-                        elif filter_name == "watch_rich_embeds":
-                            additional_embeds = msg.embeds
-                            additional_embeds_msg = "With the following embed(s):"
-
                         # Send pretty mod log embed to mod-alerts
                         await self.mod_log.send_log_message(
                             icon_url=Icons.filtering,
@@ -334,6 +346,63 @@ class Filtering(Cog):
 
                         break  # We don't want multiple filters to trigger
 
+    def _add_stats(self, name: str, match: Union[re.Match, dict, bool, List[discord.Embed]], content: str) -> Tuple[
+        str, Optional[List[discord.Embed]], Optional[str]
+    ]:
+        """Adds relevant statistical information to the relevant filter and increments the bot's stats."""
+        # Word and match stats for watch_regex
+        if name == "watch_regex":
+            surroundings = match.string[max(match.start() - 10, 0): match.end() + 10]
+            message_content = (
+                f"**Match:** '{match[0]}'\n"
+                f"**Location:** '...{escape_markdown(surroundings)}...'\n"
+                f"\n**Original Message:**\n{escape_markdown(content)}"
+            )
+        else:  # Use original content
+            message_content = content
+
+        additional_embeds = None
+        additional_embeds_msg = None
+
+        self.bot.stats.incr(f"filters.{name}")
+
+        # The function returns True for invalid invites.
+        # They have no data so additional embeds can't be created for them.
+        if name == "filter_invites" and match is not True:
+            additional_embeds = []
+            for invite, data in match.items():
+                embed = discord.Embed(description=(
+                    f"**Members:**\n{data['members']}\n"
+                    f"**Active:**\n{data['active']}"
+                ))
+                embed.set_author(name=data["name"])
+                embed.set_thumbnail(url=data["icon"])
+                embed.set_footer(text=f"Guild Invite Code: {invite}")
+                additional_embeds.append(embed)
+            additional_embeds_msg = "For the following guild(s):"
+
+        elif name == "watch_rich_embeds":
+            additional_embeds = match
+            additional_embeds_msg = "With the following embed(s):"
+
+        return message_content, additional_embeds, additional_embeds_msg
+
+    @staticmethod
+    def _check_filter(msg: Message) -> bool:
+        """Check whitelists to see if we should filter this message."""
+        role_whitelisted = False
+
+        if type(msg.author) is Member:  # Only Member has roles, not User.
+            for role in msg.author.roles:
+                if role.id in Filter.role_whitelist:
+                    role_whitelisted = True
+
+        return (
+            msg.channel.id not in Filter.channel_whitelist  # Channel not in whitelist
+            and not role_whitelisted                        # Role not in whitelist
+            and not msg.author.bot                          # Author not a bot
+        )
+
     @staticmethod
     async def _has_watch_regex_match(text: str) -> Union[bool, re.Match]:
         """
@@ -426,7 +495,7 @@ class Filtering(Cog):
         return invite_data if invite_data else False
 
     @staticmethod
-    async def _has_rich_embed(msg: Message) -> bool:
+    async def _has_rich_embed(msg: Message) -> Union[bool, List[discord.Embed]]:
         """Determines if `msg` contains any rich embeds not auto-generated from a URL."""
         if msg.embeds:
             for embed in msg.embeds:
@@ -435,7 +504,7 @@ class Filtering(Cog):
                     if not embed.url or embed.url not in urls:
                         # If `embed.url` does not exist or if `embed.url` is not part of the content
                         # of the message, it's unlikely to be an auto-generated embed by Discord.
-                        return True
+                        return msg.embeds
                     else:
                         log.trace(
                             "Found a rich embed sent by a regular user account, "
diff --git a/bot/cogs/help.py b/bot/cogs/help.py
index 5f3fc4750..3d1d6fd10 100644
--- a/bot/cogs/help.py
+++ b/bot/cogs/help.py
@@ -37,13 +37,12 @@ async def help_cleanup(bot: Bot, author: Member, message: Message) -> None:
 
     await message.add_reaction(DELETE_EMOJI)
 
-    try:
-        await bot.wait_for("reaction_add", check=check, timeout=300)
-        await message.delete()
-    except TimeoutError:
-        await message.remove_reaction(DELETE_EMOJI, bot.user)
-    except NotFound:
-        pass
+    with suppress(NotFound):
+        try:
+            await bot.wait_for("reaction_add", check=check, timeout=300)
+            await message.delete()
+        except TimeoutError:
+            await message.remove_reaction(DELETE_EMOJI, bot.user)
 
 
 class HelpQueryNotFound(ValueError):
diff --git a/bot/cogs/help_channels.py b/bot/cogs/help_channels.py
index 4d0c534b0..0c8cbb417 100644
--- a/bot/cogs/help_channels.py
+++ b/bot/cogs/help_channels.py
@@ -34,9 +34,6 @@ and will be yours until it has been inactive for {constants.HelpChannels.idle_mi
 is closed manually with `!close`. When that happens, it will be set to **dormant** and moved into \
 the **Help: Dormant** category.
 
-You may claim a new channel once every {constants.HelpChannels.claim_minutes} minutes. If you \
-currently cannot send a message in this channel, it means you are on cooldown and need to wait.
-
 Try to write the best question you can by providing a detailed description and telling us what \
 you've tried already. For more information on asking a good question, \
 check out our guide on [asking good questions]({ASKING_GUIDE_URL}).
diff --git a/bot/cogs/moderation/infractions.py b/bot/cogs/moderation/infractions.py
index 3b28526b2..8df642428 100644
--- a/bot/cogs/moderation/infractions.py
+++ b/bot/cogs/moderation/infractions.py
@@ -64,7 +64,7 @@ class Infractions(InfractionScheduler, commands.Cog):
     @command()
     async def kick(self, ctx: Context, user: Member, *, reason: t.Optional[str] = None) -> None:
         """Kick a user for the given reason."""
-        await self.apply_kick(ctx, user, reason, active=False)
+        await self.apply_kick(ctx, user, reason)
 
     @command()
     async def ban(self, ctx: Context, user: FetchedMember, *, reason: t.Optional[str] = None) -> None:
@@ -134,7 +134,7 @@ class Infractions(InfractionScheduler, commands.Cog):
     @command(hidden=True, aliases=['shadowkick', 'skick'])
     async def shadow_kick(self, ctx: Context, user: Member, *, reason: t.Optional[str] = None) -> None:
         """Kick a user for the given reason without notifying the user."""
-        await self.apply_kick(ctx, user, reason, hidden=True, active=False)
+        await self.apply_kick(ctx, user, reason, hidden=True)
 
     @command(hidden=True, aliases=['shadowban', 'sban'])
     async def shadow_ban(self, ctx: Context, user: FetchedMember, *, reason: t.Optional[str] = None) -> None:
diff --git a/bot/cogs/python_news.py b/bot/cogs/python_news.py
index adefd5c7c..0ab5738a4 100644
--- a/bot/cogs/python_news.py
+++ b/bot/cogs/python_news.py
@@ -10,7 +10,7 @@ from discord.ext.tasks import loop
 
 from bot import constants
 from bot.bot import Bot
-from bot.utils.messages import sub_clyde
+from bot.utils.webhooks import send_webhook
 
 PEPS_RSS_URL = "https://www.python.org/dev/peps/peps.rss/"
 
@@ -100,13 +100,21 @@ class PythonNews(Cog):
             ):
                 continue
 
-            msg = await self.send_webhook(
+            # Build an embed and send a webhook
+            embed = discord.Embed(
                 title=new["title"],
                 description=new["summary"],
                 timestamp=new_datetime,
                 url=new["link"],
-                webhook_profile_name=data["feed"]["title"],
-                footer=data["feed"]["title"]
+                colour=constants.Colours.soft_green
+            )
+            embed.set_footer(text=data["feed"]["title"], icon_url=AVATAR_URL)
+            msg = await send_webhook(
+                webhook=self.webhook,
+                username=data["feed"]["title"],
+                embed=embed,
+                avatar_url=AVATAR_URL,
+                wait=True,
             )
             payload["data"]["pep"].append(pep_nr)
 
@@ -161,15 +169,29 @@ class PythonNews(Cog):
 
                 content = email_information["content"]
                 link = THREAD_URL.format(id=thread["href"].split("/")[-2], list=maillist)
-                msg = await self.send_webhook(
+
+                # Build an embed and send a message to the webhook
+                embed = discord.Embed(
                     title=thread_information["subject"],
                     description=content[:500] + f"... [continue reading]({link})" if len(content) > 500 else content,
                     timestamp=new_date,
                     url=link,
-                    author=f"{email_information['sender_name']} ({email_information['sender']['address']})",
-                    author_url=MAILMAN_PROFILE_URL.format(id=email_information["sender"]["mailman_id"]),
-                    webhook_profile_name=self.webhook_names[maillist],
-                    footer=f"Posted to {self.webhook_names[maillist]}"
+                    colour=constants.Colours.soft_green
+                )
+                embed.set_author(
+                    name=f"{email_information['sender_name']} ({email_information['sender']['address']})",
+                    url=MAILMAN_PROFILE_URL.format(id=email_information["sender"]["mailman_id"]),
+                )
+                embed.set_footer(
+                    text=f"Posted to {self.webhook_names[maillist]}",
+                    icon_url=AVATAR_URL,
+                )
+                msg = await send_webhook(
+                    webhook=self.webhook,
+                    username=self.webhook_names[maillist],
+                    embed=embed,
+                    avatar_url=AVATAR_URL,
+                    wait=True,
                 )
                 payload["data"][maillist].append(thread_information["thread_id"])
 
@@ -182,38 +204,6 @@ class PythonNews(Cog):
 
         await self.bot.api_client.put("bot/bot-settings/news", json=payload)
 
-    async def send_webhook(self,
-                           title: str,
-                           description: str,
-                           timestamp: datetime,
-                           url: str,
-                           webhook_profile_name: str,
-                           footer: str,
-                           author: t.Optional[str] = None,
-                           author_url: t.Optional[str] = None,
-                           ) -> discord.Message:
-        """Send webhook entry and return sent message."""
-        embed = discord.Embed(
-            title=title,
-            description=description,
-            timestamp=timestamp,
-            url=url,
-            colour=constants.Colours.soft_green
-        )
-        if author and author_url:
-            embed.set_author(
-                name=author,
-                url=author_url
-            )
-        embed.set_footer(text=footer, icon_url=AVATAR_URL)
-
-        return await self.webhook.send(
-            embed=embed,
-            username=sub_clyde(webhook_profile_name),
-            avatar_url=AVATAR_URL,
-            wait=True
-        )
-
     async def get_thread_and_first_mail(self, maillist: str, thread_identifier: str) -> t.Tuple[t.Any, t.Any]:
         """Get mail thread and first mail from mail.python.org based on `maillist` and `thread_identifier`."""
         async with self.bot.http_session.get(
diff --git a/bot/cogs/snekbox.py b/bot/cogs/snekbox.py
index a2a7574d4..662f90869 100644
--- a/bot/cogs/snekbox.py
+++ b/bot/cogs/snekbox.py
@@ -212,7 +212,14 @@ class Snekbox(Cog):
             else:
                 self.bot.stats.incr("snekbox.python.success")
 
-            response = await ctx.send(msg)
+            filter_cog = self.bot.get_cog("Filtering")
+            filter_triggered = False
+            if filter_cog:
+                filter_triggered = await filter_cog.filter_eval(msg, ctx.message)
+            if filter_triggered:
+                response = await ctx.send("Attempt to circumvent filter detected. Moderator team has been alerted.")
+            else:
+                response = await ctx.send(msg)
             self.bot.loop.create_task(
                 wait_for_deletion(response, user_ids=(ctx.author.id,), client=ctx.bot)
             )
diff --git a/bot/cogs/watchchannels/bigbrother.py b/bot/cogs/watchchannels/bigbrother.py
index 702d371f4..4d27a6333 100644
--- a/bot/cogs/watchchannels/bigbrother.py
+++ b/bot/cogs/watchchannels/bigbrother.py
@@ -35,14 +35,29 @@ class BigBrother(WatchChannel, Cog, name="Big Brother"):
 
     @bigbrother_group.command(name='watched', aliases=('all', 'list'))
     @with_role(*MODERATION_ROLES)
-    async def watched_command(self, ctx: Context, update_cache: bool = True) -> None:
+    async def watched_command(
+        self, ctx: Context, oldest_first: bool = False, update_cache: bool = True
+    ) -> None:
         """
         Shows the users that are currently being monitored by Big Brother.
 
+        The optional kwarg `oldest_first` can be used to order the list by oldest watched.
+
+        The optional kwarg `update_cache` can be used to update the user
+        cache using the API before listing the users.
+        """
+        await self.list_watched_users(ctx, oldest_first=oldest_first, update_cache=update_cache)
+
+    @bigbrother_group.command(name='oldest')
+    @with_role(*MODERATION_ROLES)
+    async def oldest_command(self, ctx: Context, update_cache: bool = True) -> None:
+        """
+        Shows Big Brother monitored users ordered by oldest watched.
+
         The optional kwarg `update_cache` can be used to update the user
         cache using the API before listing the users.
         """
-        await self.list_watched_users(ctx, update_cache)
+        await ctx.invoke(self.watched_command, oldest_first=True, update_cache=update_cache)
 
     @bigbrother_group.command(name='watch', aliases=('w',))
     @with_role(*MODERATION_ROLES)
diff --git a/bot/cogs/watchchannels/talentpool.py b/bot/cogs/watchchannels/talentpool.py
index 33550f68e..89256e92e 100644
--- a/bot/cogs/watchchannels/talentpool.py
+++ b/bot/cogs/watchchannels/talentpool.py
@@ -38,14 +38,29 @@ class TalentPool(WatchChannel, Cog, name="Talentpool"):
 
     @nomination_group.command(name='watched', aliases=('all', 'list'))
     @with_role(*MODERATION_ROLES)
-    async def watched_command(self, ctx: Context, update_cache: bool = True) -> None:
+    async def watched_command(
+        self, ctx: Context, oldest_first: bool = False, update_cache: bool = True
+    ) -> None:
         """
         Shows the users that are currently being monitored in the talent pool.
 
+        The optional kwarg `oldest_first` can be used to order the list by oldest nomination.
+
+        The optional kwarg `update_cache` can be used to update the user
+        cache using the API before listing the users.
+        """
+        await self.list_watched_users(ctx, oldest_first=oldest_first, update_cache=update_cache)
+
+    @nomination_group.command(name='oldest')
+    @with_role(*MODERATION_ROLES)
+    async def oldest_command(self, ctx: Context, update_cache: bool = True) -> None:
+        """
+        Shows talent pool monitored users ordered by oldest nomination.
+
         The optional kwarg `update_cache` can be used to update the user
         cache using the API before listing the users.
         """
-        await self.list_watched_users(ctx, update_cache)
+        await ctx.invoke(self.watched_command, oldest_first=True, update_cache=update_cache)
 
     @nomination_group.command(name='watch', aliases=('w', 'add', 'a'))
     @with_role(*STAFF_ROLES)
diff --git a/bot/cogs/watchchannels/watchchannel.py b/bot/cogs/watchchannels/watchchannel.py
index 7c58a0fb5..044077350 100644
--- a/bot/cogs/watchchannels/watchchannel.py
+++ b/bot/cogs/watchchannels/watchchannel.py
@@ -287,10 +287,14 @@ class WatchChannel(metaclass=CogABCMeta):
 
         await self.webhook_send(embed=embed, username=msg.author.display_name, avatar_url=msg.author.avatar_url)
 
-    async def list_watched_users(self, ctx: Context, update_cache: bool = True) -> None:
+    async def list_watched_users(
+        self, ctx: Context, oldest_first: bool = False, update_cache: bool = True
+    ) -> None:
         """
         Gives an overview of the watched user list for this channel.
 
+        The optional kwarg `oldest_first` orders the list by oldest entry.
+
         The optional kwarg `update_cache` specifies whether the cache should
         be refreshed by polling the API.
         """
@@ -305,7 +309,11 @@ class WatchChannel(metaclass=CogABCMeta):
             time_delta = self._get_time_delta(inserted_at)
             lines.append(f"• <@{user_id}> (added {time_delta})")
 
+        if oldest_first:
+            lines.reverse()
+
         lines = lines or ("There's nothing here yet.",)
+
         embed = Embed(
             title=f"{self.__class__.__name__} watched users ({'updated' if update_cache else 'cached'})",
             color=Color.blue()
diff --git a/bot/constants.py b/bot/constants.py
index a1b392c82..778bc093c 100644
--- a/bot/constants.py
+++ b/bot/constants.py
@@ -395,6 +395,7 @@ class Channels(metaclass=YAMLGetter):
     dev_contrib: int
     dev_core: int
     dev_log: int
+    dm_log: int
     esoteric: int
     helpers: int
     how_to_get_help: int
@@ -427,6 +428,7 @@ class Webhooks(metaclass=YAMLGetter):
     reddit: int
     duck_pond: int
     dev_log: int
+    dm_log: int
 
 
 class Roles(metaclass=YAMLGetter):
@@ -460,6 +462,7 @@ class Guild(metaclass=YAMLGetter):
     staff_channels: List[int]
     staff_roles: List[int]
 
+
 class Keys(metaclass=YAMLGetter):
     section = "keys"
 
diff --git a/bot/converters.py b/bot/converters.py
index 898822165..4a0633951 100644
--- a/bot/converters.py
+++ b/bot/converters.py
@@ -330,6 +330,25 @@ def proxy_user(user_id: str) -> discord.Object:
     return user
 
 
+class UserMentionOrID(UserConverter):
+    """
+    Converts to a `discord.User`, but only if a mention or userID is provided.
+
+    Unlike the default `UserConverter`, it does allow conversion from name, or name#descrim.
+
+    This is useful in cases where that lookup strategy would lead to ambiguity.
+    """
+
+    async def convert(self, ctx: Context, argument: str) -> discord.User:
+        """Convert the `arg` to a `discord.User`."""
+        match = self._get_id_match(argument) or re.match(r'<@!?([0-9]+)>$', argument)
+
+        if match is not None:
+            return await super().convert(ctx, argument)
+        else:
+            raise BadArgument(f"`{argument}` is not a User mention or a User ID.")
+
+
 class FetchedUser(UserConverter):
     """
     Converts to a `discord.User` or, if it fails, a `discord.Object`.
diff --git a/bot/utils/webhooks.py b/bot/utils/webhooks.py
new file mode 100644
index 000000000..66f82ec66
--- /dev/null
+++ b/bot/utils/webhooks.py
@@ -0,0 +1,34 @@
+import logging
+from typing import Optional
+
+import discord
+from discord import Embed
+
+from bot.utils.messages import sub_clyde
+
+log = logging.getLogger(__name__)
+
+
+async def send_webhook(
+        webhook: discord.Webhook,
+        content: Optional[str] = None,
+        username: Optional[str] = None,
+        avatar_url: Optional[str] = None,
+        embed: Optional[Embed] = None,
+        wait: Optional[bool] = False
+) -> discord.Message:
+    """
+    Send a message using the provided webhook.
+
+    This uses sub_clyde() and tries for an HTTPException to ensure it doesn't crash.
+    """
+    try:
+        return await webhook.send(
+            content=content,
+            username=sub_clyde(username),
+            avatar_url=avatar_url,
+            embed=embed,
+            wait=wait,
+        )
+    except discord.HTTPException:
+        log.exception("Failed to send a message to the webhook!")
diff --git a/config-default.yml b/config-default.yml
index 19d79fa76..f2eb17b89 100644
--- a/config-default.yml
+++ b/config-default.yml
@@ -150,6 +150,7 @@ guild:
         mod_log:            &MOD_LOG        282638479504965634
         user_log:                           528976905546760203
         voice_log:                          640292421988646961
+        dm_log:                             653713721625018428
 
         # Off-topic
         off_topic_0:    291284109232308226
@@ -251,10 +252,9 @@ guild:
         duck_pond:                      637821475327311927
         dev_log:                        680501655111729222
         python_news:    &PYNEWS_WEBHOOK 704381182279942324
-
+        dm_log:                         654567640664244225
 
 filter:
-
     # What do we filter?
     filter_zalgo:       false
     filter_invites:     true
diff --git a/tests/bot/cogs/test_duck_pond.py b/tests/bot/cogs/test_duck_pond.py
index a8c0107c6..cfe10aebf 100644
--- a/tests/bot/cogs/test_duck_pond.py
+++ b/tests/bot/cogs/test_duck_pond.py
@@ -129,38 +129,6 @@ class DuckPondTests(base.LoggingTestsMixin, unittest.IsolatedAsyncioTestCase):
             ):
                 self.assertEqual(expected_return, actual_return)
 
-    def test_send_webhook_correctly_passes_on_arguments(self):
-        """The `send_webhook` method should pass the arguments to the webhook correctly."""
-        self.cog.webhook = helpers.MockAsyncWebhook()
-
-        content = "fake content"
-        username = "fake username"
-        avatar_url = "fake avatar_url"
-        embed = "fake embed"
-
-        asyncio.run(self.cog.send_webhook(content, username, avatar_url, embed))
-
-        self.cog.webhook.send.assert_called_once_with(
-            content=content,
-            username=username,
-            avatar_url=avatar_url,
-            embed=embed
-        )
-
-    def test_send_webhook_logs_when_sending_message_fails(self):
-        """The `send_webhook` method should catch a `discord.HTTPException` and log accordingly."""
-        self.cog.webhook = helpers.MockAsyncWebhook()
-        self.cog.webhook.send.side_effect = discord.HTTPException(response=MagicMock(), message="Something failed.")
-
-        log = logging.getLogger('bot.cogs.duck_pond')
-        with self.assertLogs(logger=log, level=logging.ERROR) as log_watcher:
-            asyncio.run(self.cog.send_webhook())
-
-        self.assertEqual(len(log_watcher.records), 1)
-
-        record = log_watcher.records[0]
-        self.assertEqual(record.levelno, logging.ERROR)
-
     def _get_reaction(
         self,
         emoji: typing.Union[str, helpers.MockEmoji],
@@ -280,16 +248,20 @@ class DuckPondTests(base.LoggingTestsMixin, unittest.IsolatedAsyncioTestCase):
 
     async def test_relay_message_correctly_relays_content_and_attachments(self):
         """The `relay_message` method should correctly relay message content and attachments."""
-        send_webhook_path = f"{MODULE_PATH}.DuckPond.send_webhook"
+        send_webhook_path = f"{MODULE_PATH}.send_webhook"
         send_attachments_path = f"{MODULE_PATH}.send_attachments"
+        author = MagicMock(
+            display_name="x",
+            avatar_url="https://"
+        )
 
         self.cog.webhook = helpers.MockAsyncWebhook()
 
         test_values = (
-            (helpers.MockMessage(clean_content="", attachments=[]), False, False),
-            (helpers.MockMessage(clean_content="message", attachments=[]), True, False),
-            (helpers.MockMessage(clean_content="", attachments=["attachment"]), False, True),
-            (helpers.MockMessage(clean_content="message", attachments=["attachment"]), True, True),
+            (helpers.MockMessage(author=author, clean_content="", attachments=[]), False, False),
+            (helpers.MockMessage(author=author, clean_content="message", attachments=[]), True, False),
+            (helpers.MockMessage(author=author, clean_content="", attachments=["attachment"]), False, True),
+            (helpers.MockMessage(author=author, clean_content="message", attachments=["attachment"]), True, True),
         )
 
         for message, expect_webhook_call, expect_attachment_call in test_values:
@@ -314,14 +286,14 @@ class DuckPondTests(base.LoggingTestsMixin, unittest.IsolatedAsyncioTestCase):
 
         for side_effect in side_effects:  # pragma: no cover
             send_attachments.side_effect = side_effect
-            with patch(f"{MODULE_PATH}.DuckPond.send_webhook", new_callable=AsyncMock) as send_webhook:
+            with patch(f"{MODULE_PATH}.send_webhook", new_callable=AsyncMock) as send_webhook:
                 with self.subTest(side_effect=type(side_effect).__name__):
                     with self.assertNotLogs(logger=log, level=logging.ERROR):
                         await self.cog.relay_message(message)
 
                     self.assertEqual(send_webhook.call_count, 2)
 
-    @patch(f"{MODULE_PATH}.DuckPond.send_webhook", new_callable=AsyncMock)
+    @patch(f"{MODULE_PATH}.send_webhook", new_callable=AsyncMock)
     @patch(f"{MODULE_PATH}.send_attachments", new_callable=AsyncMock)
     async def test_relay_message_handles_attachment_http_error(self, send_attachments, send_webhook):
         """The `relay_message` method should handle irretrievable attachments."""
@@ -337,6 +309,7 @@ class DuckPondTests(base.LoggingTestsMixin, unittest.IsolatedAsyncioTestCase):
                 await self.cog.relay_message(message)
 
             send_webhook.assert_called_once_with(
+                webhook=self.cog.webhook,
                 content=message.clean_content,
                 username=message.author.display_name,
                 avatar_url=message.author.avatar_url
diff --git a/tests/bot/cogs/test_snekbox.py b/tests/bot/cogs/test_snekbox.py
index cf9adbee0..98dee7a1b 100644
--- a/tests/bot/cogs/test_snekbox.py
+++ b/tests/bot/cogs/test_snekbox.py
@@ -233,6 +233,10 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
         self.cog.get_status_emoji = MagicMock(return_value=':yay!:')
         self.cog.format_output = AsyncMock(return_value=('[No output]', None))
 
+        mocked_filter_cog = MagicMock()
+        mocked_filter_cog.filter_eval = AsyncMock(return_value=False)
+        self.bot.get_cog.return_value = mocked_filter_cog
+
         await self.cog.send_eval(ctx, 'MyAwesomeCode')
         ctx.send.assert_called_once_with(
             '@LemonLemonishBeard#0042 :yay!: Return code 0.\n\n```py\n[No output]\n```'
@@ -254,6 +258,10 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
         self.cog.get_status_emoji = MagicMock(return_value=':yay!:')
         self.cog.format_output = AsyncMock(return_value=('Way too long beard', 'lookatmybeard.com'))
 
+        mocked_filter_cog = MagicMock()
+        mocked_filter_cog.filter_eval = AsyncMock(return_value=False)
+        self.bot.get_cog.return_value = mocked_filter_cog
+
         await self.cog.send_eval(ctx, 'MyAwesomeCode')
         ctx.send.assert_called_once_with(
             '@LemonLemonishBeard#0042 :yay!: Return code 0.'
@@ -275,6 +283,10 @@ class SnekboxTests(unittest.IsolatedAsyncioTestCase):
         self.cog.get_status_emoji = MagicMock(return_value=':nope!:')
         self.cog.format_output = AsyncMock()  # This function isn't called
 
+        mocked_filter_cog = MagicMock()
+        mocked_filter_cog.filter_eval = AsyncMock(return_value=False)
+        self.bot.get_cog.return_value = mocked_filter_cog
+
         await self.cog.send_eval(ctx, 'MyAwesomeCode')
         ctx.send.assert_called_once_with(
             '@LemonLemonishBeard#0042 :nope!: Return code 127.\n\n```py\nBeard got stuck in the eval\n```'