Merge branch 'main' into undeprecate-bookmark

88 files changed, 1094 insertions, 1241 deletions

diff --git a/.github/workflows/lint.yaml b/.github/workflows/lint.yaml
index 1a5e4bff..68d35d82 100644
--- a/.github/workflows/lint.yaml
+++ b/.github/workflows/lint.yaml
@@ -42,25 +42,16 @@ jobs:
       - name: Attempt bot setup
         run: "python -m bot"
         env:
-          USE_FAKEREDIS: true
-          IN_CI: true
+          REDIS_USE_FAKEREDIS: true
+          CLIENT_IN_CI: true
+          CLIENT_TOKEN: ""
 
-      # We will not run `flake8` here, as we will use a separate flake8
-      # action.
       - name: Run pre-commit hooks
-        run: SKIP=flake8 pre-commit run --all-files
+        run: SKIP=ruff pre-commit run --all-files
 
-      # Run flake8 and have it format the linting errors in the format of
-      # the GitHub Workflow command to register error annotations. This
-      # means that our flake8 output is automatically added as an error
-      # annotation to both the run result and in the "Files" tab of a
-      # pull request.
-      #
-      # Format used:
-      # ::error file={filename},line={line},col={col}::{message}
-      - name: Run flake8
-        run: "flake8 \
-        --format='::error file=%(path)s,line=%(row)d,col=%(col)d::[flake8] %(code)s: %(text)s'"
+      # Run `ruff` using github formatting to enable automatic inline annotations.
+      - name: Run ruff
+        run: "ruff check --format=github ."
 
       # Prepare the Pull Request Payload artifact. If this fails, we
       # we fail silently using the `continue-on-error` option. It's
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 7895d208..3fdd30bf 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -1,6 +1,6 @@
 repos:
   - repo: https://github.com/pre-commit/pre-commit-hooks
-    rev: v2.5.0
+    rev: v4.4.0
     hooks:
       - id: check-merge-conflict
       - id: check-toml
@@ -8,21 +8,22 @@ repos:
       - id: end-of-file-fixer
       - id: trailing-whitespace
         args: [--markdown-linebreak-ext=md]
-  - repo: https://github.com/pre-commit/pygrep-hooks
-    rev: v1.5.1
-    hooks:
-      - id: python-check-blanket-noqa
-  - repo: https://github.com/pycqa/isort
-    rev: 5.12.0
-    hooks:
-      - id: isort
-        name: isort (python)
+
   - repo: local
     hooks:
-      - id: flake8
-        name: Flake8
-        description: This hook runs flake8 within our project's poetry environment.
-        entry: poetry run flake8
+      - id: isort
+        name: isort
+        description: This hook runs isort within our project's environment.
+        entry: poetry run isort
         language: system
         types: [python]
         require_serial: true
+
+      - id: ruff
+        name: ruff
+        description: Run ruff linting
+        entry: poetry run ruff check --force-exclude
+        language: system
+        'types_or': [python, pyi]
+        require_serial: true
+        args: [--fix, --exit-non-zero-on-fix]
diff --git a/bot/__init__.py b/bot/__init__.py
index 454e235e..9ae64c2e 100644
--- a/bot/__init__.py
+++ b/bot/__init__.py
@@ -1,6 +1,6 @@
 try:
     from dotenv import load_dotenv
-    print("Found .env file, loading environment variables from it.")
+    print("Found .env file, loading environment variables from it.")  # noqa: T201
     load_dotenv(override=True)
 except ModuleNotFoundError:
     pass
diff --git a/bot/__main__.py b/bot/__main__.py
index d39e93bf..1b6b9f1e 100644
--- a/bot/__main__.py
+++ b/bot/__main__.py
@@ -19,11 +19,11 @@ log = logging.getLogger(__name__)
 async def _create_redis_session() -> RedisSession:
     """Create and connect to a redis session."""
     redis_session = RedisSession(
-        host=constants.RedisConfig.host,
-        port=constants.RedisConfig.port,
-        password=constants.RedisConfig.password,
+        host=constants.Redis.host,
+        port=constants.Redis.port,
+        password=constants.Redis.password.get_secret_value(),
         max_connections=20,
-        use_fakeredis=constants.RedisConfig.use_fakeredis,
+        use_fakeredis=constants.Redis.use_fakeredis,
         global_namespace="bot",
         decode_responses=True,
     )
@@ -81,7 +81,7 @@ async def main() -> None:
             if constants.Client.in_ci:
                 await test_bot_in_ci(_bot)
             else:
-                await _bot.start(constants.Client.token)
+                await _bot.start(constants.Client.token.get_secret_value())
 
 
 asyncio.run(main())
diff --git a/bot/bot.py b/bot/bot.py
index da19bdd9..0b20ac54 100644
--- a/bot/bot.py
+++ b/bot/bot.py
@@ -1,5 +1,4 @@
 import logging
-from typing import Optional
 
 import discord
 from discord import DiscordException, Embed
@@ -26,7 +25,7 @@ class Bot(BotBase):
     name = constants.Client.name
 
     @property
-    def member(self) -> Optional[discord.Member]:
+    def member(self) -> discord.Member | None:
         """Retrieves the guild member object for the bot."""
         guild = self.get_guild(constants.Client.guild)
         if not guild:
diff --git a/bot/constants.py b/bot/constants.py
index 7e5fa1d9..cd866a0b 100644
--- a/bot/constants.py
+++ b/bot/constants.py
@@ -1,11 +1,10 @@
 import enum
 import logging
 from os import environ
-from typing import NamedTuple
+
+from pydantic import BaseSettings, SecretStr
 
 __all__ = (
-    "Branding",
-    "Cats",
     "Channels",
     "Categories",
     "Client",
@@ -13,14 +12,12 @@ __all__ = (
     "Colours",
     "Emojis",
     "Icons",
-    "Lovefest",
     "Month",
     "Roles",
     "Tokens",
     "Wolfram",
     "Reddit",
-    "RedisConfig",
-    "RedirectOutput",
+    "Redis",
     "PYTHON_PREFIX",
     "MODERATION_ROLES",
     "STAFF_ROLES",
@@ -36,21 +33,25 @@ log = logging.getLogger(__name__)
 PYTHON_PREFIX = "!"
 
 
-class Branding:
-    cycle_frequency = int(environ.get("CYCLE_FREQUENCY", 3))  # 0: never, 1: every day, 2: every other day, ...
+class EnvConfig(BaseSettings):
+    """Our default configuration for models that should load from .env files."""
+
+    class Config:
+        """Specify what .env files to load, and how to load them."""
 
+        env_file = ".env",
+        env_file_encoding = "utf-8"
 
-class Cats:
-    cats = ["ᓚᘏᗢ", "ᘡᘏᗢ", "🐈", "ᓕᘏᗢ", "ᓇᘏᗢ", "ᓂᘏᗢ", "ᘣᘏᗢ", "ᕦᘏᗢ", "ᕂᘏᗢ"]
 
+class _Channels(EnvConfig):
+    EnvConfig.Config.env_prefix = "channels_"
 
-class Channels(NamedTuple):
     algos_and_data_structs = 650401909852864553
     bot_commands = 267659945086812160
     community_meta = 267659945086812160
     organisation = 551789653284356126
     data_science_and_ai = 366673247892275221
-    devlog = int(environ.get("CHANNEL_DEVLOG", 622895325144940554))
+    devlog = 622895325144940554
     dev_contrib = 635950537262759947
     mod_meta = 775412552795947058
     mod_tools = 775413915391098921
@@ -58,43 +59,60 @@ class Channels(NamedTuple):
     off_topic_1 = 463035241142026251
     off_topic_2 = 463035268514185226
     python_help = 1035199133436354600
-    sir_lancebot_playground = int(environ.get("CHANNEL_COMMUNITY_BOT_COMMANDS", 607247579608121354))
+    sir_lancebot_playground = 607247579608121354
     voice_chat_0 = 412357430186344448
     voice_chat_1 = 799647045886541885
     staff_voice = 541638762007101470
-    reddit = int(environ.get("CHANNEL_REDDIT", 458224812528238616))
+    reddit = 458224812528238616
+
+
+Channels = _Channels()
 
 
-class Categories(NamedTuple):
-    help_in_use = 696958401460043776
+class _Categories(EnvConfig):
+    EnvConfig.Config.env_prefix = "categories_"
+
+    python_help_system = 691405807388196926
     development = 411199786025484308
     devprojects = 787641585624940544
     media = 799054581991997460
     staff = 364918151625965579
 
 
-codejam_categories_name = "Code Jam"  # Name of the codejam team categories
+Categories = _Categories()
+
 
+class _Client(EnvConfig):
+    EnvConfig.Config.env_prefix = "client_"
 
-class Client(NamedTuple):
     name = "Sir Lancebot"
-    guild = int(environ.get("BOT_GUILD", 267624335836053506))
-    prefix = environ.get("PREFIX", ".")
-    token = environ.get("BOT_TOKEN")
-    debug = environ.get("BOT_DEBUG", "true").lower() == "true"
-    in_ci = environ.get("IN_CI", "false").lower() == "true"
-    github_bot_repo = "https://github.com/python-discord/sir-lancebot"
+    guild = 267624335836053506
+    prefix = "."
+    token: SecretStr
+    debug = True
+    in_ci = False
+    github_repo = "https://github.com/python-discord/sir-lancebot"
     # Override seasonal locks: 1 (January) to 12 (December)
-    month_override = int(environ["MONTH_OVERRIDE"]) if "MONTH_OVERRIDE" in environ else None
+    month_override: int | None = None
+
 
+Client = _Client()
+
+
+class _Logging(EnvConfig):
+    EnvConfig.Config.env_prefix = "logging_"
 
-class Logging(NamedTuple):
     debug = Client.debug
-    file_logs = environ.get("FILE_LOGS", "false").lower() == "true"
-    trace_loggers = environ.get("BOT_TRACE_LOGGERS")
+    file_logs = False
+    trace_loggers = ""
+
+
+Logging = _Logging()
 
 
 class Colours:
+    """Lookups for commonly used colours."""
+
     blue = 0x0279FD
     twitter_blue = 0x1DA1F2
     bright_green = 0x01D277
@@ -129,6 +147,8 @@ class Colours:
 
 
 class Emojis:
+    """Commonly used emojis."""
+
     cross_mark = "\u274C"
     check = "\u2611"
     envelope = "\U0001F4E8"
@@ -201,6 +221,8 @@ class Emojis:
 
 
 class Icons:
+    """URLs to commonly used icons."""
+
     questionmark = "https://cdn.discordapp.com/emojis/512367613339369475.png"
     bookmark = (
         "https://images-ext-2.discordapp.net/external/zl4oDwcmxUILY7sD9ZWE2fU5R7n6QcxEmPYSE5eddbg/"
@@ -208,11 +230,9 @@ class Icons:
     )
 
 
-class Lovefest:
-    role_id = int(environ.get("LOVEFEST_ROLE_ID", 542431903886606399))
-
-
 class Month(enum.IntEnum):
+    """Month of the year lookup. Used for in_month checks."""
+
     JANUARY = 1
     FEBRUARY = 2
     MARCH = 3
@@ -236,57 +256,72 @@ if Client.month_override is not None:
     Month(Client.month_override)
 
 
-class Roles(NamedTuple):
+class _Roles(EnvConfig):
+
+    EnvConfig.Config.env_prefix = "roles_"
+
     owners = 267627879762755584
-    admins = int(environ.get("BOT_ADMIN_ROLE_ID", 267628507062992896))
+    admins = 267628507062992896
     moderation_team = 267629731250176001
-    helpers = int(environ.get("ROLE_HELPERS", 267630620367257601))
+    helpers = 267630620367257601
     core_developers = 587606783669829632
-    everyone = int(environ.get("BOT_GUILD", 267624335836053506))
+    everyone = Client.guild
+
+    lovefest = 542431903886606399
+
 
+Roles = _Roles()
 
-class Tokens(NamedTuple):
-    giphy = environ.get("GIPHY_TOKEN")
-    aoc_session_cookie = environ.get("AOC_SESSION_COOKIE")
-    omdb = environ.get("OMDB_API_KEY")
-    youtube = environ.get("YOUTUBE_API_KEY")
-    tmdb = environ.get("TMDB_API_KEY")
-    nasa = environ.get("NASA_API_KEY")
-    igdb_client_id = environ.get("IGDB_CLIENT_ID")
-    igdb_client_secret = environ.get("IGDB_CLIENT_SECRET")
-    github = environ.get("GITHUB_TOKEN")
-    unsplash_access_key = environ.get("UNSPLASH_KEY")
 
+class _Tokens(EnvConfig):
+    EnvConfig.Config.env_prefix = "tokens_"
 
-class Wolfram(NamedTuple):
-    user_limit_day = int(environ.get("WOLFRAM_USER_LIMIT_DAY", 10))
-    guild_limit_day = int(environ.get("WOLFRAM_GUILD_LIMIT_DAY", 67))
-    key = environ.get("WOLFRAM_API_KEY")
+    giphy: SecretStr = ""
+    youtube: SecretStr = ""
+    tmdb: SecretStr = ""
+    nasa: SecretStr = ""
+    igdb_client_id: SecretStr = ""
+    igdb_client_secret: SecretStr = ""
+    github: SecretStr = ""
+    unsplash: SecretStr = ""
 
 
-class RedisConfig(NamedTuple):
-    host = environ.get("REDIS_HOST", "redis.default.svc.cluster.local")
-    port = environ.get("REDIS_PORT", 6379)
-    password = environ.get("REDIS_PASSWORD")
-    use_fakeredis = environ.get("USE_FAKEREDIS", "false").lower() == "true"
+Tokens = _Tokens()
 
 
-class Source:
-    github = "https://github.com/python-discord/sir-lancebot"
-    github_avatar_url = "https://avatars1.githubusercontent.com/u/9919"
+class _Wolfram(EnvConfig):
+    EnvConfig.Config.env_prefix = "wolfram_"
+    user_limit_day = 10
+    guild_limit_day = 67
+    key: SecretStr = ""
 
 
-class RedirectOutput:
-    delete_delay: int = 10
+Wolfram = _Wolfram()
 
 
-class Reddit:
+class _Redis(EnvConfig):
+    EnvConfig.Config.env_prefix = "redis_"
+
+    host = "redis.default.svc.cluster.local"
+    port = 6379
+    password: SecretStr = ""
+    use_fakeredis = False
+
+
+Redis = _Redis()
+
+
+class _Reddit(EnvConfig):
+    EnvConfig.Config.env_prefix = "reddit_"
+
     subreddits = ["r/Python"]
 
-    client_id = environ.get("REDDIT_CLIENT_ID")
-    secret = environ.get("REDDIT_SECRET")
-    webhook = int(environ.get("REDDIT_WEBHOOK", 635408384794951680))
+    client_id: SecretStr = ""
+    secret: SecretStr = ""
+    webhook = 635408384794951680
+
 
+Reddit = _Reddit()
 
 # Default role combinations
 MODERATION_ROLES = {Roles.moderation_team, Roles.admins, Roles.owners}
diff --git a/bot/exts/avatar_modification/_effects.py b/bot/exts/avatar_modification/_effects.py
index f1c2e6d1..fcc62ebb 100644
--- a/bot/exts/avatar_modification/_effects.py
+++ b/bot/exts/avatar_modification/_effects.py
@@ -1,8 +1,8 @@
 import math
 import random
+from collections.abc import Callable
 from io import BytesIO
 from pathlib import Path
-from typing import Callable, Optional
 
 import discord
 from PIL import Image, ImageDraw, ImageOps
@@ -55,7 +55,7 @@ class PfpEffects:
 
     @staticmethod
     def crop_avatar_circle(avatar: Image.Image) -> Image.Image:
-        """This crops the avatar given into a circle."""
+        """Crop the avatar given into a circle."""
         mask = Image.new("L", avatar.size, 0)
         draw = ImageDraw.Draw(mask)
         draw.ellipse((0, 0) + avatar.size, fill=255)
@@ -64,7 +64,7 @@ class PfpEffects:
 
     @staticmethod
     def crop_ring(ring: Image.Image, px: int) -> Image.Image:
-        """This crops the given ring into a circle."""
+        """Crop the given ring into a circle."""
         mask = Image.new("L", ring.size, 0)
         draw = ImageDraw.Draw(mask)
         draw.ellipse((0, 0) + ring.size, fill=255)
@@ -108,7 +108,7 @@ class PfpEffects:
         return image
 
     @staticmethod
-    def easterify_effect(image: Image.Image, overlay_image: Optional[Image.Image] = None) -> Image.Image:
+    def easterify_effect(image: Image.Image, overlay_image: Image.Image | None = None) -> Image.Image:
         """
         Applies the easter effect to the given image.
 
diff --git a/bot/exts/avatar_modification/avatar_modify.py b/bot/exts/avatar_modification/avatar_modify.py
index 6d1f26f6..4eae269f 100644
--- a/bot/exts/avatar_modification/avatar_modify.py
+++ b/bot/exts/avatar_modification/avatar_modify.py
@@ -4,9 +4,10 @@ import logging
 import math
 import string
 import unicodedata
+from collections.abc import Callable
 from concurrent.futures import ThreadPoolExecutor
 from pathlib import Path
-from typing import Callable, Optional, TypeVar, Union
+from typing import TypeVar
 
 import discord
 from discord.ext import commands
@@ -64,7 +65,7 @@ class AvatarModify(commands.Cog):
     def __init__(self, bot: Bot):
         self.bot = bot
 
-    async def _fetch_user(self, user_id: int) -> Optional[discord.User]:
+    async def _fetch_user(self, user_id: int) -> discord.User | None:
         """
         Fetches a user and handles errors.
 
@@ -120,7 +121,7 @@ class AvatarModify(commands.Cog):
         await ctx.send(embed=embed, file=file)
 
     @avatar_modify.command(name="reverse", root_aliases=("reverse",))
-    async def reverse(self, ctx: commands.Context, *, text: Optional[str]) -> None:
+    async def reverse(self, ctx: commands.Context, *, text: str | None) -> None:
         """
         Reverses the sent text.
 
@@ -157,9 +158,9 @@ class AvatarModify(commands.Cog):
             await ctx.send(embed=embed, file=file)
 
     @avatar_modify.command(aliases=("easterify",), root_aliases=("easterify", "avatareasterify"))
-    async def avatareasterify(self, ctx: commands.Context, *colours: Union[discord.Colour, str]) -> None:
+    async def avatareasterify(self, ctx: commands.Context, *colours: discord.Colour | str) -> None:
         """
-        This "Easterifies" the user's avatar.
+        Easterify the user's avatar.
 
         Given colours will produce a personalised egg in the corner, similar to the egg_decorate command.
         If colours are not given, a nice little chocolate bunny will sit in the corner.
@@ -168,13 +169,14 @@ class AvatarModify(commands.Cog):
         """
         async def send(*args, **kwargs) -> str:
             """
-            This replaces the original ctx.send.
+            Replace the original ctx.send.
 
             When invoking the egg decorating command, the egg itself doesn't print to to the channel.
-            Returns the message content so that if any errors occur, the error message can be output.
+            Return the message content so that if any errors occur, the error message can be output.
             """
             if args:
                 return args[0]
+            return None
 
         async with ctx.typing():
             user = await self._fetch_user(ctx.author.id)
@@ -248,11 +250,11 @@ class AvatarModify(commands.Cog):
     )
     async def prideavatar(self, ctx: commands.Context, option: str = "lgbt", pixels: int = 64) -> None:
         """
-        This surrounds an avatar with a border of a specified LGBT flag.
+        Surround an avatar with a border of a specified LGBT flag.
 
-        This defaults to the LGBT rainbow flag if none is given.
+        Default to the LGBT rainbow flag if none is given.
         The amount of pixels can be given which determines the thickness of the flag border.
-        This has a maximum of 512px and defaults to a 64px border.
+        A maximum of 512px is enforced, defaults to a 64px border.
         The full image is 1024x1024.
         """
         option = option.lower()
@@ -272,7 +274,7 @@ class AvatarModify(commands.Cog):
 
     @prideavatar.command()
     async def flags(self, ctx: commands.Context) -> None:
-        """This lists the flags that can be used with the prideavatar command."""
+        """Lists the flags that can be used with the prideavatar command."""
         choices = sorted(set(GENDER_OPTIONS.values()))
         options = "• " + "\n• ".join(choices)
         embed = discord.Embed(
@@ -288,7 +290,7 @@ class AvatarModify(commands.Cog):
         brief="Spookify a user's avatar."
     )
     async def spookyavatar(self, ctx: commands.Context) -> None:
-        """This "spookifies" the user's avatar, with a random *spooky* effect."""
+        """Spookify the user's avatar, with a random *spooky* effect."""
         user = await self._fetch_user(ctx.author.id)
         if not user:
             await ctx.send(f"{Emojis.cross_mark} Could not get user info.")
diff --git a/bot/exts/core/error_handler.py b/bot/exts/core/error_handler.py
index 04ab55d7..81b923fd 100644
--- a/bot/exts/core/error_handler.py
+++ b/bot/exts/core/error_handler.py
@@ -2,14 +2,13 @@ import logging
 import math
 import random
 from collections.abc import Iterable
-from typing import Union
 
 from discord import Embed, Message
 from discord.ext import commands
 from sentry_sdk import push_scope
 
 from bot.bot import Bot
-from bot.constants import Channels, Colours, ERROR_REPLIES, NEGATIVE_REPLIES, RedirectOutput
+from bot.constants import Channels, Colours, ERROR_REPLIES, NEGATIVE_REPLIES
 from bot.utils.commands import get_command_suggestions
 from bot.utils.decorators import InChannelCheckFailure, InMonthCheckFailure
 from bot.utils.exceptions import APIError, MovedCommandError, UserNotPlayingError
@@ -17,6 +16,7 @@ from bot.utils.exceptions import APIError, MovedCommandError, UserNotPlayingErro
 log = logging.getLogger(__name__)
 
 
+DELETE_DELAY = 10
 QUESTION_MARK_ICON = "https://cdn.discordapp.com/emojis/512367613339369475.png"
 
 
@@ -35,7 +35,7 @@ class CommandErrorHandler(commands.Cog):
             logging.debug("Cooldown counter reverted as the command was not used correctly.")
 
     @staticmethod
-    def error_embed(message: str, title: Union[Iterable, str] = ERROR_REPLIES) -> Embed:
+    def error_embed(message: str, title: Iterable | str = ERROR_REPLIES) -> Embed:
         """Build a basic embed with red colour and either a random error title or a title provided."""
         embed = Embed(colour=Colours.soft_red)
         if isinstance(title, str):
@@ -59,7 +59,7 @@ class CommandErrorHandler(commands.Cog):
 
         error = getattr(error, "original", error)
         logging.debug(
-            f"Error Encountered: {type(error).__name__} - {str(error)}, "
+            f"Error Encountered: {type(error).__name__} - {error!s}, "
             f"Command: {ctx.command}, "
             f"Author: {ctx.author}, "
             f"Channel: {ctx.channel}"
@@ -71,7 +71,7 @@ class CommandErrorHandler(commands.Cog):
                 await self.send_command_suggestion(ctx, ctx.invoked_with)
             return
 
-        if isinstance(error, (InChannelCheckFailure, InMonthCheckFailure)):
+        if isinstance(error, InChannelCheckFailure | InMonthCheckFailure):
             await ctx.send(embed=self.error_embed(str(error), NEGATIVE_REPLIES), delete_after=7.5)
             return
 
@@ -156,7 +156,7 @@ class CommandErrorHandler(commands.Cog):
             if ctx.guild is not None:
                 scope.set_extra("jump_to", ctx.message.jump_url)
 
-            log.exception(f"Unhandled command error: {str(error)}", exc_info=error)
+            log.exception(f"Unhandled command error: {error!s}", exc_info=error)
 
     async def send_command_suggestion(self, ctx: commands.Context, command_name: str) -> None:
         """Sends user similar commands if any can be found."""
@@ -185,7 +185,7 @@ class CommandErrorHandler(commands.Cog):
             e.description = "\n".join(
                 misspelled_content.replace(command_name, cmd, 1) for cmd in command_suggestions
             )
-            await ctx.send(embed=e, delete_after=RedirectOutput.delete_delay)
+            await ctx.send(embed=e, delete_after=DELETE_DELAY)
 
 
 async def setup(bot: Bot) -> None:
diff --git a/bot/exts/core/extensions.py b/bot/exts/core/extensions.py
index 1d22cf37..87ef2ed1 100644
--- a/bot/exts/core/extensions.py
+++ b/bot/exts/core/extensions.py
@@ -2,7 +2,6 @@ import functools
 import logging
 from collections.abc import Mapping
 from enum import Enum
-from typing import Optional
 
 from discord import Colour, Embed
 from discord.ext import commands
@@ -48,7 +47,7 @@ class Extension(commands.Converter):
 
         if argument in ctx.bot.all_extensions:
             return argument
-        elif (qualified_arg := f"{exts.__name__}.{argument}") in ctx.bot.all_extensions:
+        if (qualified_arg := f"{exts.__name__}.{argument}") in ctx.bot.all_extensions:
             return qualified_arg
 
         matches = []
@@ -63,10 +62,9 @@ class Extension(commands.Converter):
                 f":x: `{argument}` is an ambiguous extension name. "
                 f"Please use one of the following fully-qualified names.```\n{names}\n```"
             )
-        elif matches:
+        if matches:
             return matches[0]
-        else:
-            raise commands.BadArgument(f":x: Could not find the extension `{argument}`.")
+        raise commands.BadArgument(f":x: Could not find the extension `{argument}`.")
 
 
 class Extensions(commands.Cog):
@@ -86,7 +84,7 @@ class Extensions(commands.Cog):
         Load extensions given their fully qualified or unqualified names.
 
         If '\*' or '\*\*' is given as the name, all unloaded extensions will be loaded.
-        """  # noqa: W605
+        """
         if not extensions:
             await self.bot.invoke_help_command(ctx)
             return
@@ -103,7 +101,7 @@ class Extensions(commands.Cog):
         Unload currently loaded extensions given their fully qualified or unqualified names.
 
         If '\*' or '\*\*' is given as the name, all loaded extensions will be unloaded.
-        """  # noqa: W605
+        """
         if not extensions:
             await self.bot.invoke_help_command(ctx)
             return
@@ -129,7 +127,7 @@ class Extensions(commands.Cog):
 
         If '\*' is given as the name, all currently loaded extensions will be reloaded.
         If '\*\*' is given as the name, all extensions, including unloaded ones, will be reloaded.
-        """  # noqa: W605
+        """
         if not extensions:
             await self.bot.invoke_help_command(ctx)
             return
@@ -220,7 +218,7 @@ class Extensions(commands.Cog):
 
         return msg
 
-    async def manage(self, action: Action, ext: str) -> tuple[str, Optional[str]]:
+    async def manage(self, action: Action, ext: str) -> tuple[str, str | None]:
         """Apply an action to an extension and return the status message and any error message."""
         verb = action.name.lower()
         error_msg = None
diff --git a/bot/exts/core/help.py b/bot/exts/core/help.py
index 30deaff4..9f96a333 100644
--- a/bot/exts/core/help.py
+++ b/bot/exts/core/help.py
@@ -3,7 +3,7 @@ import asyncio
 import itertools
 import logging
 from contextlib import suppress
-from typing import NamedTuple, Optional, Union
+from typing import NamedTuple
 
 from discord import Colour, Embed, HTTPException, Message, Reaction, User
 from discord.ext import commands
@@ -38,7 +38,7 @@ class Cog(NamedTuple):
 log = logging.getLogger(__name__)
 
 
-class HelpQueryNotFound(ValueError):
+class HelpQueryNotFoundError(ValueError):
     """
     Raised when a HelpSession Query doesn't match a command or cog.
 
@@ -49,7 +49,7 @@ class HelpQueryNotFound(ValueError):
     """
 
     def __init__(
-            self, arg: str, possible_matches: Optional[list[str]] = None, *, parent_command: Optional[Command] = None
+            self, arg: str, possible_matches: list[str] | None = None, *, parent_command: Command | None = None
     ) -> None:
         super().__init__(arg)
         self.possible_matches = possible_matches
@@ -117,7 +117,7 @@ class HelpSession:
         self._timeout_task = None
         self.reset_timeout()
 
-    def _get_query(self, query: str) -> Union[Command, Cog]:
+    def _get_query(self, query: str) -> Command | Cog | None:
         """Attempts to match the provided query with a valid command or cog."""
         command = self._bot.get_command(query)
         if command:
@@ -151,6 +151,7 @@ class HelpSession:
             )
 
         self._handle_not_found(query)
+        return None
 
     def _handle_not_found(self, query: str) -> None:
         """
@@ -164,11 +165,11 @@ class HelpSession:
             parent_command = self._bot.get_command(parent)
 
             if parent_command:
-                raise HelpQueryNotFound('Invalid Subcommand.', parent_command=parent_command)
+                raise HelpQueryNotFoundError("Invalid Subcommand.", parent_command=parent_command)
 
         similar_commands = get_command_suggestions(list(self._bot.all_commands.keys()), query)
 
-        raise HelpQueryNotFound(f'Query "{query}" not found.', similar_commands)
+        raise HelpQueryNotFoundError(f'Query "{query}" not found.', similar_commands)
 
     async def timeout(self, seconds: int = 30) -> None:
         """Waits for a set number of seconds, then stops the help session."""
@@ -178,9 +179,8 @@ class HelpSession:
     def reset_timeout(self) -> None:
         """Cancels the original timeout task and sets it again from the start."""
         # cancel original if it exists
-        if self._timeout_task:
-            if not self._timeout_task.cancelled():
-                self._timeout_task.cancel()
+        if self._timeout_task and not self._timeout_task.cancelled():
+            self._timeout_task.cancel()
 
         # recreate the timeout task
         self._timeout_task = self._bot.loop.create_task(self.timeout())
@@ -252,8 +252,7 @@ class HelpSession:
                 pass
 
             return f"**{cmd.cog_name}**"
-        else:
-            return "**\u200bNo Category:**"
+        return "**\u200bNo Category:**"
 
     def _get_command_params(self, cmd: Command) -> str:
         """
@@ -286,8 +285,7 @@ class HelpSession:
             # if required
             else:
                 results.append(f"<{name}>")
-
-        return f"{cmd.qualified_name} {' '.join(results)}"
+        return " ".join([cmd.qualified_name, *results])
 
     async def build_pages(self) -> None:
         """Builds the list of content pages to be paginated through in the help message, as a list of str."""
@@ -305,7 +303,7 @@ class HelpSession:
             paginator.add_line(f"*{self.description}*")
 
         # list all children commands of the queried object
-        if isinstance(self.query, (commands.GroupMixin, Cog)):
+        if isinstance(self.query, commands.GroupMixin | Cog):
             await self._list_child_commands(paginator)
 
         self._pages = paginator.pages
@@ -418,7 +416,7 @@ class HelpSession:
         """Returns an Embed with the requested page formatted within."""
         embed = Embed()
 
-        if isinstance(self.query, (commands.Command, Cog)) and page_number > 0:
+        if isinstance(self.query, commands.Command | Cog) and page_number > 0:
             title = f'Command Help | "{self.query.name}"'
         else:
             title = self.title
@@ -518,7 +516,7 @@ class Help(DiscordCog):
         """Shows Command Help."""
         try:
             await HelpSession.start(ctx, *commands)
-        except HelpQueryNotFound as error:
+        except HelpQueryNotFoundError as error:
 
             # Send help message of parent command if subcommand is invalid.
             if cmd := error.parent_command:
diff --git a/bot/exts/core/internal_eval/_helpers.py b/bot/exts/core/internal_eval/_helpers.py
index 5b2f8f5d..34ef7fef 100644
--- a/bot/exts/core/internal_eval/_helpers.py
+++ b/bot/exts/core/internal_eval/_helpers.py
@@ -8,7 +8,7 @@ import logging
 import sys
 import traceback
 import types
-from typing import Any, Optional, Union
+from typing import Any
 
 log = logging.getLogger(__name__)
 
@@ -120,7 +120,7 @@ class EvalContext:
         log.trace(f"Updating {self._locals} with {locals_}")
         self._locals.update(locals_)
 
-    def prepare_eval(self, code: str) -> Optional[str]:
+    def prepare_eval(self, code: str) -> str | None:
         """Prepare an evaluation by processing the code and setting up the context."""
         self.code = code
 
@@ -149,7 +149,7 @@ class EvalContext:
         compiled_code = compile(self.eval_tree, filename=INTERNAL_EVAL_FRAMENAME, mode="exec")
 
         log.trace("Executing the compiled code with the desired namespace environment")
-        exec(compiled_code, self.locals)  # noqa: B102,S102
+        exec(compiled_code, self.locals)  # noqa: S102
 
         log.trace("Awaiting the created evaluation wrapper coroutine.")
         await self.function()
@@ -212,7 +212,7 @@ class CaptureLastExpression(ast.NodeTransformer):
         self.tree = tree
         self.last_node = list(ast.iter_child_nodes(tree))[-1]
 
-    def visit_Expr(self, node: ast.Expr) -> Union[ast.Expr, ast.Assign]:  # noqa: N802
+    def visit_Expr(self, node: ast.Expr) -> ast.Expr | ast.Assign:  # noqa: N802
         """
         Replace the Expr node that is last child node of Module with an assignment.
 
@@ -230,7 +230,7 @@ class CaptureLastExpression(ast.NodeTransformer):
         right_hand_side = list(ast.iter_child_nodes(node))[0]
 
         assignment = ast.Assign(
-            targets=[ast.Name(id='_value_last_expression', ctx=ast.Store())],
+            targets=[ast.Name(id="_value_last_expression", ctx=ast.Store())],
             value=right_hand_side,
             lineno=node.lineno,
             col_offset=0,
diff --git a/bot/exts/core/internal_eval/_internal_eval.py b/bot/exts/core/internal_eval/_internal_eval.py
index 2daf8ef9..f5188c1f 100644
--- a/bot/exts/core/internal_eval/_internal_eval.py
+++ b/bot/exts/core/internal_eval/_internal_eval.py
@@ -1,7 +1,6 @@
 import logging
 import re
 import textwrap
-from typing import Optional
 
 import discord
 from discord.ext import commands
@@ -84,7 +83,7 @@ class InternalEval(commands.Cog):
 
         return shortened_output
 
-    async def _upload_output(self, output: str) -> Optional[str]:
+    async def _upload_output(self, output: str) -> str | None:
         """Upload `internal eval` output to our pastebin and return the url."""
         data = self.shorten_output(output, max_length=MAX_LENGTH)
         try:
diff --git a/bot/exts/core/source.py b/bot/exts/core/source.py
index f771eaca..7c67bcb5 100644
--- a/bot/exts/core/source.py
+++ b/bot/exts/core/source.py
@@ -1,15 +1,17 @@
 import inspect
 from pathlib import Path
-from typing import Optional
 
 from discord import Embed
 from discord.ext import commands
 
 from bot.bot import Bot
-from bot.constants import Channels, Source, WHITELISTED_CHANNELS
+from bot.constants import Channels, WHITELISTED_CHANNELS
 from bot.utils.converters import SourceConverter, SourceType
 from bot.utils.decorators import whitelist_override
 
+GITHUB_BOT_URL = "https://github.com/python-discord/sir-lancebot"
+BOT_AVATAR_URL = "https://avatars1.githubusercontent.com/u/9919"
+
 
 class BotSource(commands.Cog):
     """Displays information about the bot's source code."""
@@ -20,15 +22,15 @@ class BotSource(commands.Cog):
         """Display information and a GitHub link to the source code of a command, tag, or cog."""
         if not source_item:
             embed = Embed(title="Sir Lancebot's GitHub Repository")
-            embed.add_field(name="Repository", value=f"[Go to GitHub]({Source.github})")
-            embed.set_thumbnail(url=Source.github_avatar_url)
+            embed.add_field(name="Repository", value=f"[Go to GitHub]({GITHUB_BOT_URL})")
+            embed.set_thumbnail(url=BOT_AVATAR_URL)
             await ctx.send(embed=embed)
             return
 
         embed = await self.build_embed(source_item)
         await ctx.send(embed=embed)
 
-    def get_source_link(self, source_item: SourceType) -> tuple[str, str, Optional[int]]:
+    def get_source_link(self, source_item: SourceType) -> tuple[str, str, int | None]:
         """
         Build GitHub link of source item, return this link, file location and first line number.
 
@@ -58,11 +60,11 @@ class BotSource(commands.Cog):
 
         file_location = Path(filename).relative_to(Path.cwd()).as_posix()
 
-        url = f"{Source.github}/blob/main/{file_location}{lines_extension}"
+        url = f"{GITHUB_BOT_URL}/blob/main/{file_location}{lines_extension}"
 
         return url, file_location, first_line_no or None
 
-    async def build_embed(self, source_object: SourceType) -> Optional[Embed]:
+    async def build_embed(self, source_object: SourceType) -> Embed | None:
         """Build embed based on source object."""
         url, location, first_line = self.get_source_link(source_object)
 
@@ -74,7 +76,7 @@ class BotSource(commands.Cog):
             description = source_object.description.splitlines()[0]
 
         embed = Embed(title=title, description=description)
-        embed.set_thumbnail(url=Source.github_avatar_url)
+        embed.set_thumbnail(url=BOT_AVATAR_URL)
         embed.add_field(name="Source Code", value=f"[Go to GitHub]({url})")
         line_text = f":{first_line}" if first_line else ""
         embed.set_footer(text=f"{location}{line_text}")
diff --git a/bot/exts/events/hacktoberfest/hacktober-issue-finder.py b/bot/exts/events/hacktoberfest/hacktober_issue_finder.py
index aeffc8d7..69aa3924 100644
--- a/bot/exts/events/hacktoberfest/hacktober-issue-finder.py
+++ b/bot/exts/events/hacktoberfest/hacktober_issue_finder.py
@@ -1,7 +1,6 @@
-import datetime
 import logging
 import random
-from typing import Optional
+from datetime import UTC, datetime
 
 import discord
 from discord.ext import commands
@@ -18,7 +17,7 @@ REQUEST_HEADERS = {
     "User-Agent": "Python Discord Hacktoberbot",
     "Accept": "application / vnd.github.v3 + json"
 }
-if GITHUB_TOKEN := Tokens.github:
+if GITHUB_TOKEN := Tokens.github.get_secret_value():
     REQUEST_HEADERS["Authorization"] = f"token {GITHUB_TOKEN}"
 
 
@@ -28,9 +27,9 @@ class HacktoberIssues(commands.Cog):
     def __init__(self, bot: Bot):
         self.bot = bot
         self.cache_normal = None
-        self.cache_timer_normal = datetime.datetime(1, 1, 1)
+        self.cache_timer_normal = datetime(1, 1, 1, tzinfo=UTC)
         self.cache_beginner = None
-        self.cache_timer_beginner = datetime.datetime(1, 1, 1)
+        self.cache_timer_beginner = datetime(1, 1, 1, tzinfo=UTC)
 
     @in_month(Month.OCTOBER)
     @commands.command()
@@ -49,7 +48,7 @@ class HacktoberIssues(commands.Cog):
             embed = self.format_embed(issue)
         await ctx.send(embed=embed)
 
-    async def get_issues(self, ctx: commands.Context, option: str) -> Optional[dict]:
+    async def get_issues(self, ctx: commands.Context, option: str) -> dict | None:
         """Get a list of the python issues with the label 'hacktoberfest' from the Github api."""
         if option == "beginner":
             if (ctx.message.created_at.replace(tzinfo=None) - self.cache_timer_beginner).seconds <= 60:
diff --git a/bot/exts/events/hacktoberfest/hacktoberstats.py b/bot/exts/events/hacktoberfest/hacktoberstats.py
index c29e24b0..c7fd3601 100644
--- a/bot/exts/events/hacktoberfest/hacktoberstats.py
+++ b/bot/exts/events/hacktoberfest/hacktoberstats.py
@@ -2,8 +2,7 @@ import logging
 import random
 import re
 from collections import Counter
-from datetime import datetime, timedelta
-from typing import Optional, Union
+from datetime import UTC, datetime, timedelta
 from urllib.parse import quote_plus
 
 import discord
@@ -16,7 +15,7 @@ from bot.utils.decorators import in_month
 
 log = logging.getLogger(__name__)
 
-CURRENT_YEAR = datetime.now().year  # Used to construct GH API query
+CURRENT_YEAR = datetime.now(tz=UTC).year  # Used to construct GH API query
 PRS_FOR_SHIRT = 4  # Minimum number of PRs before a shirt is awarded
 REVIEW_DAYS = 14  # number of days needed after PR can be mature
 
@@ -24,8 +23,8 @@ REQUEST_HEADERS = {"User-Agent": "Python Discord Hacktoberbot"}
 # using repo topics API during preview period requires an accept header
 GITHUB_TOPICS_ACCEPT_HEADER = {"Accept": "application/vnd.github.mercy-preview+json"}
 if GITHUB_TOKEN := Tokens.github:
-    REQUEST_HEADERS["Authorization"] = f"token {GITHUB_TOKEN}"
-    GITHUB_TOPICS_ACCEPT_HEADER["Authorization"] = f"token {GITHUB_TOKEN}"
+    REQUEST_HEADERS["Authorization"] = f"token {GITHUB_TOKEN.get_secret_value()}"
+    GITHUB_TOPICS_ACCEPT_HEADER["Authorization"] = f"token {GITHUB_TOKEN.get_secret_value()}"
 
 GITHUB_NONEXISTENT_USER_MESSAGE = (
     "The listed users cannot be searched either because the users do not exist "
@@ -185,7 +184,7 @@ class HacktoberStats(commands.Cog):
         logging.info(f"Hacktoberfest PR built for GitHub user '{github_username}'")
         return stats_embed
 
-    async def get_october_prs(self, github_username: str) -> Optional[list[dict]]:
+    async def get_october_prs(self, github_username: str) -> list[dict] | None:
         """
         Query GitHub's API for PRs created during the month of October by github_username.
 
@@ -234,9 +233,8 @@ class HacktoberStats(commands.Cog):
             # Ignore logging non-existent users or users we do not have permission to see
             if api_message == GITHUB_NONEXISTENT_USER_MESSAGE:
                 log.debug(f"No GitHub user found named '{github_username}'")
-                return
-            else:
-                log.error(f"GitHub API request for '{github_username}' failed with message: {api_message}")
+                return None
+            log.error(f"GitHub API request for '{github_username}' failed with message: {api_message}")
             return []  # No October PRs were found due to error
 
         if jsonresp["total_count"] == 0:
@@ -246,7 +244,7 @@ class HacktoberStats(commands.Cog):
 
         logging.info(f"Found {len(jsonresp['items'])} Hacktoberfest PRs for GitHub user: '{github_username}'")
         outlist = []  # list of pr information dicts that will get returned
-        oct3 = datetime(int(CURRENT_YEAR), 10, 3, 23, 59, 59, tzinfo=None)
+        oct3 = datetime(int(CURRENT_YEAR), 10, 3, 23, 59, 59, tzinfo=UTC)
         hackto_topics = {}  # cache whether each repo has the appropriate topic (bool values)
         for item in jsonresp["items"]:
             shortname = self._get_shortname(item["repository_url"])
@@ -255,15 +253,14 @@ class HacktoberStats(commands.Cog):
                 "repo_shortname": shortname,
                 "created_at": datetime.strptime(
                     item["created_at"], "%Y-%m-%dT%H:%M:%SZ"
-                ),
+                ).replace(tzinfo=UTC),
                 "number": item["number"]
             }
 
             # If the PR has 'invalid' or 'spam' labels, the PR must be
             # either merged or approved for it to be included
-            if self._has_label(item, ["invalid", "spam"]):
-                if not await self._is_accepted(itemdict):
-                    continue
+            if self._has_label(item, ["invalid", "spam"]) and not await self._is_accepted(itemdict):
+                continue
 
             # PRs before oct 3 no need to check for topics
             # continue the loop if 'hacktoberfest-accepted' is labelled then
@@ -302,7 +299,7 @@ class HacktoberStats(commands.Cog):
             return await resp.json()
 
     @staticmethod
-    def _has_label(pr: dict, labels: Union[list[str], str]) -> bool:
+    def _has_label(pr: dict, labels: list[str] | str) -> bool:
         """
         Check if a PR has label 'labels'.
 
@@ -313,7 +310,7 @@ class HacktoberStats(commands.Cog):
             return False
         if isinstance(labels, str) and any(label["name"].casefold() == labels for label in pr["labels"]):
             return True
-        for item in labels:
+        for item in labels:  # noqa: SIM110
             if any(label["name"].casefold() == item for label in pr["labels"]):
                 return True
         return False
@@ -350,10 +347,7 @@ class HacktoberStats(commands.Cog):
             return False
 
         # loop through reviews and check for approval
-        for item in jsonresp2:
-            if item.get("status") == "APPROVED":
-                return True
-        return False
+        return any(item.get("status") == "APPROVED" for item in jsonresp2)
 
     @staticmethod
     def _get_shortname(in_url: str) -> str:
@@ -378,8 +372,8 @@ class HacktoberStats(commands.Cog):
         PRs that are accepted must either be merged, approved, or labelled
         'hacktoberfest-accepted.
         """
-        now = datetime.now()
-        oct3 = datetime(CURRENT_YEAR, 10, 3, 23, 59, 59, tzinfo=None)
+        now = datetime.now(tz=UTC)
+        oct3 = datetime(CURRENT_YEAR, 10, 3, 23, 59, 59, tzinfo=UTC)
         in_review = []
         accepted = []
         for pr in prs:
@@ -420,8 +414,7 @@ class HacktoberStats(commands.Cog):
         """Return "contribution" or "contributions" based on the value of n."""
         if n == 1:
             return "contribution"
-        else:
-            return "contributions"
+        return "contributions"
 
     @staticmethod
     def _author_mention_from_context(ctx: commands.Context) -> tuple[str, str]:
@@ -434,4 +427,6 @@ class HacktoberStats(commands.Cog):
 
 async def setup(bot: Bot) -> None:
     """Load the Hacktober Stats Cog."""
+    if not Tokens.github:
+        log.warning("No GitHub token was provided. The HacktoberStats Cog won't be fully functional.")
     await bot.add_cog(HacktoberStats(bot))
diff --git a/bot/exts/events/hacktoberfest/timeleft.py b/bot/exts/events/hacktoberfest/timeleft.py
index f470e932..8f46d798 100644
--- a/bot/exts/events/hacktoberfest/timeleft.py
+++ b/bot/exts/events/hacktoberfest/timeleft.py
@@ -1,5 +1,5 @@
 import logging
-from datetime import datetime
+from datetime import UTC, datetime
 
 from discord.ext import commands
 
@@ -9,25 +9,25 @@ log = logging.getLogger(__name__)
 
 
 class TimeLeft(commands.Cog):
-    """A Cog that tells you how long left until Hacktober is over!"""
+    """A Cog that tells users how long left until Hacktober is over!"""
 
     def in_hacktober(self) -> bool:
         """Return True if the current time is within Hacktoberfest."""
         _, end, start = self.load_date()
 
-        now = datetime.utcnow()
+        now = datetime.now(tz=UTC)
 
         return start <= now <= end
 
     @staticmethod
     def load_date() -> tuple[datetime, datetime, datetime]:
-        """Return of a tuple of the current time and the end and start times of the next October."""
-        now = datetime.utcnow()
+        """Return of a tuple of the current time and the end and start times of the next Hacktober."""
+        now = datetime.now(tz=UTC)
         year = now.year
         if now.month > 10:
             year += 1
-        end = datetime(year, 11, 1, 12)  # November 1st 12:00 (UTC-12:00)
-        start = datetime(year, 9, 30, 10)  # September 30th 10:00 (UTC+14:00)
+        end = datetime(year, 11, 1, 12, tzinfo=UTC)  # November 1st 12:00 (UTC-12:00)
+        start = datetime(year, 9, 30, 10, tzinfo=UTC)  # September 30th 10:00 (UTC+14:00)
         return now, end, start
 
     @commands.command()
diff --git a/bot/exts/events/trivianight/_game.py b/bot/exts/events/trivianight/_game.py
index 8b012a17..15126f60 100644
--- a/bot/exts/events/trivianight/_game.py
+++ b/bot/exts/events/trivianight/_game.py
@@ -1,7 +1,8 @@
 import time
+from collections.abc import Iterable
 from random import randrange
 from string import ascii_uppercase
-from typing import Iterable, NamedTuple, Optional, TypedDict
+from typing import NamedTuple, TypedDict
 
 DEFAULT_QUESTION_POINTS = 10
 DEFAULT_QUESTION_TIME = 20
@@ -14,8 +15,8 @@ class QuestionData(TypedDict):
     description: str
     answers: list[str]
     correct: str
-    points: Optional[int]
-    time: Optional[int]
+    points: int | None
+    time: int | None
 
 
 class UserGuess(NamedTuple):
@@ -26,15 +27,15 @@ class UserGuess(NamedTuple):
     elapsed: float
 
 
-class QuestionClosed(RuntimeError):
+class QuestionClosedError(RuntimeError):
     """Exception raised when the question is not open for guesses anymore."""
 
 
-class AlreadyUpdated(RuntimeError):
+class AlreadyUpdatedError(RuntimeError):
     """Exception raised when the user has already updated their guess once."""
 
 
-class AllQuestionsVisited(RuntimeError):
+class AllQuestionsVisitedError(RuntimeError):
     """Exception raised when all of the questions have been visited."""
 
 
@@ -90,10 +91,10 @@ class Question:
     def _update_guess(self, user: int, answer: str) -> UserGuess:
         """Update an already existing guess."""
         if self._started is None:
-            raise QuestionClosed("Question is not open for answers.")
+            raise QuestionClosedError("Question is not open for answers.")
 
         if self._guesses[user][1] is False:
-            raise AlreadyUpdated(f"User({user}) has already updated their guess once.")
+            raise AlreadyUpdatedError(f"User({user}) has already updated their guess once.")
 
         self._guesses[user] = (answer, False, time.perf_counter() - self._started)
         return self._guesses[user]
@@ -104,7 +105,7 @@ class Question:
             return self._update_guess(user, answer)
 
         if self._started is None:
-            raise QuestionClosed("Question is not open for answers.")
+            raise QuestionClosedError("Question is not open for answers.")
 
         self._guesses[user] = (answer, True, time.perf_counter() - self._started)
         return self._guesses[user]
@@ -126,7 +127,7 @@ class TriviaNightGame:
         self._questions = [Question(q) for q in data]
         # A copy of the questions to keep for `.trivianight list`
         self._all_questions = list(self._questions)
-        self.current_question: Optional[Question] = None
+        self.current_question: Question | None = None
         self._points = {}
         self._speed = {}
 
@@ -148,7 +149,7 @@ class TriviaNightGame:
             except IndexError:
                 raise ValueError(f"Question number {number} does not exist.")
         elif len(self._questions) == 0:
-            raise AllQuestionsVisited("All of the questions have been visited.")
+            raise AllQuestionsVisitedError("All of the questions have been visited.")
         else:
             question = self._questions.pop(randrange(len(self._questions)))
 
diff --git a/bot/exts/events/trivianight/_questions.py b/bot/exts/events/trivianight/_questions.py
index 5f1046dc..a0dd545e 100644
--- a/bot/exts/events/trivianight/_questions.py
+++ b/bot/exts/events/trivianight/_questions.py
@@ -7,7 +7,7 @@ from discord.ui import Button, View
 
 from bot.constants import Colours, NEGATIVE_REPLIES
 
-from ._game import AlreadyUpdated, Question, QuestionClosed
+from ._game import AlreadyUpdatedError, Question, QuestionClosedError
 from ._scoreboard import Scoreboard
 
 
@@ -29,7 +29,7 @@ class AnswerButton(Button):
         """
         try:
             guess = self.question.guess(interaction.user.id, self.label)
-        except AlreadyUpdated:
+        except AlreadyUpdatedError:
             await interaction.response.send_message(
                 embed=Embed(
                     title=choice(NEGATIVE_REPLIES),
@@ -39,7 +39,7 @@ class AnswerButton(Button):
                 ephemeral=True
             )
             return
-        except QuestionClosed:
+        except QuestionClosedError:
             await interaction.response.send_message(
                 embed=Embed(
                     title=choice(NEGATIVE_REPLIES),
@@ -91,7 +91,7 @@ class QuestionView(View):
             - text: A string that represents the question description to 'unicodeify'
         """
         return "".join(
-            f"{letter}\u200b" if letter not in ('\n', '\t', '`', 'p', 'y') else letter
+            f"{letter}\u200b" if letter not in ("\n", "\t", "`", "p", "y") else letter
             for idx, letter in enumerate(text)
         )
 
@@ -127,13 +127,13 @@ class QuestionView(View):
         if len(guesses) != 0:
             answers_chosen = {
                 answer_choice: len(
-                    tuple(filter(lambda x: x[0] == answer_choice, guesses.values()))  # noqa: B023
+                    tuple(filter(lambda x: x[0] == answer_choice, guesses.values()))
                 )
                 for answer_choice in labels
             }
 
             answers_chosen = dict(
-                sorted(list(answers_chosen.items()), key=lambda item: item[1], reverse=True)
+                sorted(answers_chosen.items(), key=lambda item: item[1], reverse=True)
             )
 
             for answer, people_answered in answers_chosen.items():
diff --git a/bot/exts/events/trivianight/trivianight.py b/bot/exts/events/trivianight/trivianight.py
index 10435551..e0db45d8 100644
--- a/bot/exts/events/trivianight/trivianight.py
+++ b/bot/exts/events/trivianight/trivianight.py
@@ -1,7 +1,6 @@
 import asyncio
 from json import JSONDecodeError, loads
 from random import choice
-from typing import Optional
 
 from discord import Embed
 from discord.ext import commands
@@ -10,7 +9,7 @@ from bot.bot import Bot
 from bot.constants import Colours, NEGATIVE_REPLIES, POSITIVE_REPLIES, Roles
 from bot.utils.pagination import LinePaginator
 
-from ._game import AllQuestionsVisited, TriviaNightGame
+from ._game import AllQuestionsVisitedError, TriviaNightGame
 from ._questions import QuestionView
 from ._scoreboard import Scoreboard
 
@@ -23,8 +22,8 @@ class TriviaNightCog(commands.Cog):
 
     def __init__(self, bot: Bot):
         self.bot = bot
-        self.game: Optional[TriviaNightGame] = None
-        self.scoreboard: Optional[Scoreboard] = None
+        self.game: TriviaNightGame | None = None
+        self.scoreboard: Scoreboard | None = None
         self.question_closed: asyncio.Event = None
 
     @commands.group(aliases=["tn"], invoke_without_command=True)
@@ -46,7 +45,7 @@ class TriviaNightCog(commands.Cog):
 
     @trivianight.command()
     @commands.has_any_role(*TRIVIA_NIGHT_ROLES)
-    async def load(self, ctx: commands.Context, *, to_load: Optional[str]) -> None:
+    async def load(self, ctx: commands.Context, *, to_load: str | None) -> None:
         """
         Loads a JSON file from the provided attachment or argument.
 
@@ -76,8 +75,7 @@ class TriviaNightCog(commands.Cog):
         elif not to_load:
             raise commands.BadArgument("You didn't attach an attachment nor link a message!")
         elif (
-            to_load.startswith("https://discord.com/channels")
-            or to_load.startswith("https://discordapp.com/channels")
+            to_load.startswith(("https://discord.com/channels", "https://discordapp.com/channels"))
         ):
             channel_id, message_id = to_load.split("/")[-2:]
             channel = await ctx.guild.fetch_channel(int(channel_id))
@@ -92,7 +90,7 @@ class TriviaNightCog(commands.Cog):
         try:
             serialized_json = loads(json_text)
         except JSONDecodeError as error:
-            raise commands.BadArgument(f"Looks like something went wrong:\n{str(error)}")
+            raise commands.BadArgument(f"Looks like something went wrong:\n{error!s}")
 
         self.game = TriviaNightGame(serialized_json)
         self.question_closed = asyncio.Event()
@@ -107,7 +105,7 @@ class TriviaNightCog(commands.Cog):
 
         await ctx.send(embed=success_embed)
 
-    @trivianight.command(aliases=('next',))
+    @trivianight.command(aliases=("next",))
     @commands.has_any_role(*TRIVIA_NIGHT_ROLES)
     async def question(self, ctx: commands.Context, question_number: str = None) -> None:
         """
@@ -135,7 +133,7 @@ class TriviaNightCog(commands.Cog):
 
         try:
             next_question = self.game.next_question(question_number)
-        except AllQuestionsVisited:
+        except AllQuestionsVisitedError:
             error_embed = Embed(
                 title=choice(NEGATIVE_REPLIES),
                 description="All of the questions have been used.",
diff --git a/bot/exts/fun/anagram.py b/bot/exts/fun/anagram.py
index d8ea6a55..8210d1d5 100644
--- a/bot/exts/fun/anagram.py
+++ b/bot/exts/fun/anagram.py
@@ -15,7 +15,7 @@ log = logging.getLogger(__name__)
 TIME_LIMIT = 60
 
 # anagram.json file contains all the anagrams
-with open(Path("bot/resources/fun/anagram.json"), "r") as f:
+with open(Path("bot/resources/fun/anagram.json")) as f:
     ANAGRAMS_ALL = json.load(f)
 
 
diff --git a/bot/exts/fun/battleship.py b/bot/exts/fun/battleship.py
index a8039cf2..4a552605 100644
--- a/bot/exts/fun/battleship.py
+++ b/bot/exts/fun/battleship.py
@@ -4,7 +4,6 @@ import random
 import re
 from dataclasses import dataclass
 from functools import partial
-from typing import Optional
 
 import discord
 from discord.ext import commands
@@ -19,7 +18,7 @@ log = logging.getLogger(__name__)
 class Square:
     """Each square on the battleship grid - if they contain a boat and if they've been aimed at."""
 
-    boat: Optional[str]
+    boat: str | None
     aimed: bool
 
 
@@ -31,8 +30,8 @@ EmojiSet = dict[tuple[bool, bool], str]
 class Player:
     """Each player in the game - their messages for the boards and their current grid."""
 
-    user: Optional[discord.Member]
-    board: Optional[discord.Message]
+    user: discord.Member | None
+    board: discord.Message | None
     opponent_board: discord.Message
     grid: Grid
 
@@ -110,10 +109,10 @@ class Game:
 
         self.gameover: bool = False
 
-        self.turn: Optional[Player] = None
-        self.next: Optional[Player] = None
+        self.turn: Player | None = None
+        self.next: Player | None = None
 
-        self.match: Optional[re.Match] = None
+        self.match: re.Match | None = None
         self.surrender: bool = False
 
         self.setup_grids()
@@ -135,7 +134,7 @@ class Game:
             for row in player.grid
         ]
 
-        rows = ["".join([number] + row) for number, row in zip(NUMBERS, grid)]
+        rows = ["".join([number] + row) for number, row in zip(NUMBERS, grid, strict=True)]
         return "\n".join([LETTERS] + rows)
 
     @staticmethod
@@ -215,7 +214,7 @@ class Game:
             (self.p1, "board"), (self.p2, "board")
         )
 
-        for board, location in zip(boards, locations):
+        for board, location in zip(boards, locations, strict=True):
             player, attr = location
             if getattr(player, attr):
                 await getattr(player, attr).edit(content=board)
@@ -232,8 +231,9 @@ class Game:
             if not self.match:
                 self.bot.loop.create_task(message.add_reaction(CROSS_EMOJI))
             return bool(self.match)
+        return None
 
-    async def take_turn(self) -> Optional[Square]:
+    async def take_turn(self) -> Square | None:
         """Lets the player who's turn it is choose a square."""
         square = None
         turn_message = await self.turn.user.send(
diff --git a/bot/exts/fun/catify.py b/bot/exts/fun/catify.py
index 6e8c75ba..c1677cd8 100644
--- a/bot/exts/fun/catify.py
+++ b/bot/exts/fun/catify.py
@@ -1,21 +1,22 @@
 import random
 from contextlib import suppress
-from typing import Optional
 
 from discord import AllowedMentions, Embed, Forbidden
 from discord.ext import commands
 
 from bot.bot import Bot
-from bot.constants import Cats, Colours, NEGATIVE_REPLIES
+from bot.constants import Colours, NEGATIVE_REPLIES
 from bot.utils import helpers
 
+CATS = ["ᓚᘏᗢ", "ᘡᘏᗢ", "🐈", "ᓕᘏᗢ", "ᓇᘏᗢ", "ᓂᘏᗢ", "ᘣᘏᗢ", "ᕦᘏᗢ", "ᕂᘏᗢ"]
+
 
 class Catify(commands.Cog):
     """Cog for the catify command."""
 
     @commands.command(aliases=("ᓚᘏᗢify", "ᓚᘏᗢ"))
     @commands.cooldown(1, 5, commands.BucketType.user)
-    async def catify(self, ctx: commands.Context, *, text: Optional[str]) -> None:
+    async def catify(self, ctx: commands.Context, *, text: str | None) -> None:
         """
         Convert the provided text into a cat themed sentence by interspercing cats throughout text.
 
@@ -36,13 +37,12 @@ class Catify(commands.Cog):
                 await ctx.send(embed=embed)
                 return
 
-            else:
-                display_name += f" | {random.choice(Cats.cats)}"
+            display_name += f" | {random.choice(CATS)}"
 
-                await ctx.send(f"Your catified nickname is: `{display_name}`", allowed_mentions=AllowedMentions.none())
+            await ctx.send(f"Your catified nickname is: `{display_name}`", allowed_mentions=AllowedMentions.none())
 
-                with suppress(Forbidden):
-                    await ctx.author.edit(nick=display_name)
+            with suppress(Forbidden):
+                await ctx.author.edit(nick=display_name)
         else:
             if len(text) >= 1500:
                 embed = Embed(
@@ -58,21 +58,21 @@ class Catify(commands.Cog):
                 name = name.lower()
                 if "cat" in name:
                     if random.randint(0, 5) == 5:
-                        string_list[index] = name.replace("cat", f"**{random.choice(Cats.cats)}**")
+                        string_list[index] = name.replace("cat", f"**{random.choice(CATS)}**")
                     else:
-                        string_list[index] = name.replace("cat", random.choice(Cats.cats))
-                for element in Cats.cats:
-                    if element in name:
-                        string_list[index] = name.replace(element, "cat")
+                        string_list[index] = name.replace("cat", random.choice(CATS))
+                for cat in CATS:
+                    if cat in name:
+                        string_list[index] = name.replace(cat, "cat")
 
             string_len = len(string_list) // 3 or len(string_list)
 
             for _ in range(random.randint(1, string_len)):
                 # insert cat at random index
                 if random.randint(0, 5) == 5:
-                    string_list.insert(random.randint(0, len(string_list)), f"**{random.choice(Cats.cats)}**")
+                    string_list.insert(random.randint(0, len(string_list)), f"**{random.choice(CATS)}**")
                 else:
-                    string_list.insert(random.randint(0, len(string_list)), random.choice(Cats.cats))
+                    string_list.insert(random.randint(0, len(string_list)), random.choice(CATS))
 
             text = helpers.suppress_links(" ".join(string_list))
             await ctx.send(
diff --git a/bot/exts/fun/connect_four.py b/bot/exts/fun/connect_four.py
index 0d870a6e..6544dc48 100644
--- a/bot/exts/fun/connect_four.py
+++ b/bot/exts/fun/connect_four.py
@@ -1,7 +1,6 @@
 import asyncio
 import random
 from functools import partial
-from typing import Optional, Union
 
 import discord
 import emojis
@@ -14,8 +13,8 @@ from bot.constants import Emojis
 NUMBERS = list(Emojis.number_emojis.values())
 CROSS_EMOJI = Emojis.incident_unactioned
 
-Coordinate = Optional[tuple[int, int]]
-EMOJI_CHECK = Union[discord.Emoji, str]
+Coordinate = tuple[int, int] | None
+EMOJI_CHECK = discord.Emoji | str
 
 
 class Game:
@@ -26,7 +25,7 @@ class Game:
         bot: Bot,
         channel: discord.TextChannel,
         player1: discord.Member,
-        player2: Optional[discord.Member],
+        player2: discord.Member | None,
         tokens: list[str],
         size: int = 7
     ):
@@ -73,7 +72,7 @@ class Game:
             await self.message.edit(content=None, embed=embed)
 
     async def game_over(
-        self, action: str, player1: Union[ClientUser, Member], player2: Union[ClientUser, Member]
+        self, action: str, player1: ClientUser | Member, player2: ClientUser | Member
     ) -> None:
         """Announces to public chat."""
         if action == "win":
@@ -134,12 +133,12 @@ class Game:
                 reaction, user = await self.bot.wait_for("reaction_add", check=self.predicate, timeout=30.0)
             except asyncio.TimeoutError:
                 await self.channel.send(f"{self.player_active.mention}, you took too long. Game over!")
-                return
+                return None
             else:
                 await message.delete()
                 if str(reaction.emoji) == CROSS_EMOJI:
                     await self.game_over("quit", self.player_active, self.player_inactive)
-                    return
+                    return None
 
                 await self.message.remove_reaction(reaction, user)
 
@@ -197,7 +196,7 @@ class AI:
                     break
         return possible_coords
 
-    def check_ai_win(self, coord_list: list[Coordinate]) -> Optional[Coordinate]:
+    def check_ai_win(self, coord_list: list[Coordinate]) -> Coordinate:
         """
         Check AI win.
 
@@ -205,12 +204,13 @@ class AI:
         with 10% chance of not winning and returning None
         """
         if random.randint(1, 10) == 1:
-            return
+            return None
         for coords in coord_list:
             if self.game.check_win(coords, 2):
                 return coords
+        return None
 
-    def check_player_win(self, coord_list: list[Coordinate]) -> Optional[Coordinate]:
+    def check_player_win(self, coord_list: list[Coordinate]) -> Coordinate | None:
         """
         Check Player win.
 
@@ -218,17 +218,18 @@ class AI:
         from winning with 25% of not blocking them  and returning None.
         """
         if random.randint(1, 4) == 1:
-            return
+            return None
         for coords in coord_list:
             if self.game.check_win(coords, 1):
                 return coords
+        return None
 
     @staticmethod
     def random_coords(coord_list: list[Coordinate]) -> Coordinate:
         """Picks a random coordinate from the possible ones."""
         return random.choice(coord_list)
 
-    def play(self) -> Union[Coordinate, bool]:
+    def play(self) -> Coordinate | bool:
         """
         Plays for the AI.
 
@@ -331,7 +332,7 @@ class ConnectFour(commands.Cog):
     @staticmethod
     def check_emojis(
         e1: EMOJI_CHECK, e2: EMOJI_CHECK
-    ) -> tuple[bool, Optional[str]]:
+    ) -> tuple[bool, str | None]:
         """Validate the emojis, the user put."""
         if isinstance(e1, str) and emojis.count(e1) != 1:
             return False, e1
@@ -342,7 +343,7 @@ class ConnectFour(commands.Cog):
     async def _play_game(
         self,
         ctx: commands.Context,
-        user: Optional[discord.Member],
+        user: discord.Member | None,
         board_size: int,
         emoji1: str,
         emoji2: str
diff --git a/bot/exts/fun/duck_game.py b/bot/exts/fun/duck_game.py
index a2612e51..fbdc9ea2 100644
--- a/bot/exts/fun/duck_game.py
+++ b/bot/exts/fun/duck_game.py
@@ -42,7 +42,7 @@ CARD_HEIGHT = 97
 
 EMOJI_WRONG = "\u274C"
 
-ANSWER_REGEX = re.compile(r'^\D*(\d+)\D+(\d+)\D+(\d+)\D*$')
+ANSWER_REGEX = re.compile(r"^\D*(\d+)\D+(\d+)\D+(\d+)\D*$")
 
 HELP_TEXT = """
 **Each card has 4 features**
@@ -97,7 +97,7 @@ def get_card_image(card: tuple[int]) -> Image:
 
 def as_trinary(card: tuple[int]) -> int:
     """Find the card's unique index by interpreting its features as trinary."""
-    return int(''.join(str(x) for x in card), base=3)
+    return int("".join(str(x) for x in card), base=3)
 
 
 class DuckGame:
@@ -156,7 +156,7 @@ class DuckGame:
                     # which is prevented by the triangle iteration.
                     completion = tuple(
                         feat_a if feat_a == feat_b else 3-feat_a-feat_b
-                        for feat_a, feat_b in zip(card_a, card_b)
+                        for feat_a, feat_b in zip(card_a, card_b, strict=True)
                     )
                     try:
                         idx_c = self.board.index(completion)
@@ -178,8 +178,8 @@ class DuckGamesDirector(commands.Cog):
         self.current_games = {}
 
     @commands.group(
-        name='duckduckduckgoose',
-        aliases=['dddg', 'ddg', 'duckduckgoose', 'duckgoose'],
+        name="duckduckduckgoose",
+        aliases=["dddg", "ddg", "duckduckgoose", "duckgoose"],
         invoke_without_command=True
     )
     @commands.cooldown(rate=1, per=2, type=commands.BucketType.channel)
@@ -218,7 +218,7 @@ class DuckGamesDirector(commands.Cog):
             return
 
         game = self.current_games[channel.id]
-        if msg.content.strip().lower() == 'goose':
+        if msg.content.strip().lower() == "goose":
             # If all of the solutions have been claimed, i.e. the "goose" call is correct.
             if len(game.solutions) == len(game.claimed_answers):
                 try:
@@ -248,7 +248,7 @@ class DuckGamesDirector(commands.Cog):
         if answer in game.solutions:
             game.claimed_answers[answer] = msg.author
             game.scores[msg.author] += CORRECT_SOLN
-            await self.append_to_found_embed(game, f"{str(answer):12s}  -  {msg.author.display_name}")
+            await self.append_to_found_embed(game, f"{answer!s:12s}  -  {msg.author.display_name}")
         else:
             await msg.add_reaction(EMOJI_WRONG)
             game.scores[msg.author] += INCORRECT_SOLN
diff --git a/bot/exts/fun/game.py b/bot/exts/fun/game.py
index a8b0b3a0..b2b18f04 100644
--- a/bot/exts/fun/game.py
+++ b/bot/exts/fun/game.py
@@ -2,9 +2,9 @@ import difflib
 import logging
 import random
 import re
-from datetime import datetime as dt, timedelta
+from datetime import UTC, datetime, timedelta
 from enum import IntEnum
-from typing import Any, Optional
+from typing import Any
 
 from aiohttp import ClientSession
 from discord import Embed
@@ -20,8 +20,8 @@ from bot.utils.pagination import ImagePaginator, LinePaginator
 # Base URL of IGDB API
 BASE_URL = "https://api.igdb.com/v4"
 
-CLIENT_ID = Tokens.igdb_client_id
-CLIENT_SECRET = Tokens.igdb_client_secret
+CLIENT_ID = Tokens.igdb_client_id.get_secret_value()
+CLIENT_SECRET = Tokens.igdb_client_secret.get_secret_value()
 
 # The number of seconds before expiry that we attempt to re-fetch a new access token
 ACCESS_TOKEN_RENEWAL_WINDOW = 60*60*24*2
@@ -255,7 +255,7 @@ class Games(Cog):
                 self.genres[genre_name] = genre
 
     @group(name="games", aliases=("game",), invoke_without_command=True)
-    async def games(self, ctx: Context, amount: Optional[int] = 5, *, genre: Optional[str]) -> None:
+    async def games(self, ctx: Context, amount: int | None = 5, *, genre: str | None) -> None:
         """
         Get random game(s) by genre from IGDB. Use .games genres command to get all available genres.
 
@@ -293,7 +293,8 @@ class Games(Cog):
                     f"{f'Maybe you meant `{display_possibilities}`?' if display_possibilities else ''}"
                 )
                 return
-            elif len(possibilities) == 1:
+
+            if len(possibilities) == 1:
                 games = await self.get_games_list(
                     amount, self.genres[possibilities[0][1]], offset=random.randint(0, 150)
                 )
@@ -368,8 +369,8 @@ class Games(Cog):
     async def get_games_list(
         self,
         amount: int,
-        genre: Optional[str] = None,
-        sort: Optional[str] = None,
+        genre: str | None = None,
+        sort: str | None = None,
         additional_body: str = "",
         offset: int = 0
     ) -> list[dict[str, Any]]:
@@ -398,10 +399,13 @@ class Games(Cog):
     async def create_page(self, data: dict[str, Any]) -> tuple[str, str]:
         """Create content of Game Page."""
         # Create cover image URL from template
-        url = COVER_URL.format(**{"image_id": data["cover"]["image_id"] if "cover" in data else ""})
+        url = COVER_URL.format(image_id=data.get("cover", {}).get("image_id", ""))
 
         # Get release date separately with checking
-        release_date = dt.utcfromtimestamp(data["first_release_date"]).date() if "first_release_date" in data else "?"
+        if "first_release_date" in data:
+            release_date = datetime.fromtimestamp(data["first_release_date"], tz=UTC).date()
+        else:
+            release_date = "?"
 
         # Create Age Ratings value
         rating = ", ".join(
@@ -434,7 +438,7 @@ class Games(Cog):
         lines = []
 
         # Define request body of IGDB API request and do request
-        body = SEARCH_BODY.format(**{"term": search_term})
+        body = SEARCH_BODY.format(term=search_term)
 
         async with self.http_session.post(url=f"{BASE_URL}/games", data=body, headers=self.headers) as resp:
             data = await resp.json()
@@ -460,10 +464,10 @@ class Games(Cog):
         returning results.
         """
         # Create request body from template
-        body = COMPANIES_LIST_BODY.format(**{
-            "limit": limit,
-            "offset": offset
-        })
+        body = COMPANIES_LIST_BODY.format(
+            limit=limit,
+            offset=offset,
+        )
 
         async with self.http_session.post(url=f"{BASE_URL}/companies", data=body, headers=self.headers) as resp:
             return await resp.json()
@@ -471,10 +475,10 @@ class Games(Cog):
     async def create_company_page(self, data: dict[str, Any]) -> tuple[str, str]:
         """Create good formatted Game Company page."""
         # Generate URL of company logo
-        url = LOGO_URL.format(**{"image_id": data["logo"]["image_id"] if "logo" in data else ""})
+        url = LOGO_URL.format(image_id=data.get("logo", {}).get("image_id", ""))
 
         # Try to get found date of company
-        founded = dt.utcfromtimestamp(data["start_date"]).date() if "start_date" in data else "?"
+        founded = datetime.fromtimestamp(data["start_date"], tz=UTC).date() if "start_date" in data else "?"
 
         # Generate list of games, that company have developed or published
         developed = ", ".join(game["name"] for game in data["developed"]) if "developed" in data else "?"
diff --git a/bot/exts/fun/hangman.py b/bot/exts/fun/hangman.py
index f385a955..7a02a552 100644
--- a/bot/exts/fun/hangman.py
+++ b/bot/exts/fun/hangman.py
@@ -89,7 +89,7 @@ class Hangman(commands.Cog):
         word = choice(filtered_words)
         # `pretty_word` is used for comparing the indices where the guess of the user is similar to the word
         # The `user_guess` variable is prettified by adding spaces between every dash, and so is the `pretty_word`
-        pretty_word = ''.join([f"{letter} " for letter in word])[:-1]
+        pretty_word = "".join([f"{letter} " for letter in word])[:-1]
         user_guess = ("_ " * len(word))[:-1]
         tries = 6
         guessed_letters = set()
@@ -104,7 +104,7 @@ class Hangman(commands.Cog):
         ))
 
         # Game loop
-        while user_guess.replace(' ', '') != word:
+        while user_guess.replace(" ", "") != word:
             # Edit the message to the current state of the game
             await original_message.edit(embed=self.create_embed(tries, user_guess))
 
@@ -136,7 +136,7 @@ class Hangman(commands.Cog):
                 continue
 
             # Checks for repeated guesses
-            elif normalized_content in guessed_letters:
+            if normalized_content in guessed_letters:
                 already_guessed_embed = Embed(
                     title=choice(NEGATIVE_REPLIES),
                     description=f"You have already guessed `{normalized_content}`, try again!",
@@ -146,12 +146,11 @@ class Hangman(commands.Cog):
                 continue
 
             # Checks for correct guesses from the user
-            elif normalized_content in word:
+            if normalized_content in word:
                 positions = {idx for idx, letter in enumerate(pretty_word) if letter == normalized_content}
                 user_guess = "".join(
                     [normalized_content if index in positions else dash for index, dash in enumerate(user_guess)]
                 )
-
             else:
                 tries -= 1
 
diff --git a/bot/exts/fun/latex.py b/bot/exts/fun/latex.py
index 8af05413..12f2d0b6 100644
--- a/bot/exts/fun/latex.py
+++ b/bot/exts/fun/latex.py
@@ -1,19 +1,22 @@
 import hashlib
+import logging
 import os
 import re
 import string
 from io import BytesIO
 from pathlib import Path
-from typing import BinaryIO, Optional
+from typing import BinaryIO
 
 import discord
 from PIL import Image
+from aiohttp import web
 from discord.ext import commands
 
 from bot.bot import Bot
 from bot.constants import Channels, WHITELISTED_CHANNELS
 from bot.utils.decorators import whitelist_override
 
+log = logging.getLogger(__name__)
 FORMATTED_CODE_REGEX = re.compile(
     r"(?P<delim>(?P<block>```)|``?)"        # code delimiter: 1-3 backticks; (?P=block) only matches if it's a block
     r"(?(block)(?:(?P<lang>[a-z]+)\n)?)"    # if we're in a block, match optional language (only letters plus newline)
@@ -45,8 +48,7 @@ def _prepare_input(text: str) -> str:
     """Extract latex from a codeblock, if it is in one."""
     if match := FORMATTED_CODE_REGEX.match(text):
         return match.group("code")
-    else:
-        return text
+    return text
 
 
 def _process_image(data: bytes, out_file: BinaryIO) -> None:
@@ -65,7 +67,7 @@ def _process_image(data: bytes, out_file: BinaryIO) -> None:
 class InvalidLatexError(Exception):
     """Represents an error caused by invalid latex."""
 
-    def __init__(self, logs: Optional[str]):
+    def __init__(self, logs: str | None):
         super().__init__(logs)
         self.logs = logs
 
@@ -89,7 +91,7 @@ class Latex(commands.Cog):
         ) as response:
             _process_image(await response.read(), out_file)
 
-    async def _upload_to_pastebin(self, text: str) -> Optional[str]:
+    async def _upload_to_pastebin(self, text: str) -> str | None:
         """Uploads `text` to the paste service, returning the url if successful."""
         try:
             async with self.bot.http_session.post(
@@ -100,9 +102,8 @@ class Latex(commands.Cog):
                 response_json = await response.json()
             if "key" in response_json:
                 return f"{PASTEBIN_URL}/{response_json['key']}.txt?noredirect"
-        except Exception:
-            # 400 (Bad Request) means there are too many characters
-            pass
+        except web.HTTPClientError as e:
+            log.info("Error when uploading latex output to pastebin. %s", e)
 
     @commands.command()
     @commands.max_concurrency(1, commands.BucketType.guild, wait=True)
@@ -112,7 +113,7 @@ class Latex(commands.Cog):
         query = _prepare_input(query)
 
         # the hash of the query is used as the filename in the cache.
-        query_hash = hashlib.md5(query.encode()).hexdigest()
+        query_hash = hashlib.md5(query.encode()).hexdigest()  # noqa: S324
         image_path = CACHE_DIRECTORY / f"{query_hash}.png"
         async with ctx.typing():
             if not image_path.exists():
diff --git a/bot/exts/fun/madlibs.py b/bot/exts/fun/madlibs.py
index 075dde75..c14e8a3a 100644
--- a/bot/exts/fun/madlibs.py
+++ b/bot/exts/fun/madlibs.py
@@ -117,7 +117,7 @@ class Madlibs(commands.Cog):
         self.checks.remove(author_check)
 
         story = []
-        for value, blank in zip(random_template["value"], blanks):
+        for value, blank in zip(random_template["value"], blanks, strict=True):
             story.append(f"{value}__{blank}__")
 
         # In each story template, there is always one more "value"
diff --git a/bot/exts/fun/minesweeper.py b/bot/exts/fun/minesweeper.py
index f16b1db2..69be88d3 100644
--- a/bot/exts/fun/minesweeper.py
+++ b/bot/exts/fun/minesweeper.py
@@ -2,7 +2,6 @@ import logging
 from collections.abc import Iterator
 from dataclasses import dataclass
 from random import randint, random
-from typing import Union
 
 import discord
 from discord.ext import commands
@@ -33,7 +32,7 @@ MESSAGE_MAPPING = {
 log = logging.getLogger(__name__)
 
 
-GameBoard = list[list[Union[str, int]]]
+GameBoard = list[list[str | int]]
 
 
 @dataclass
@@ -205,9 +204,9 @@ class Minesweeper(commands.Cog):
             for y in range(10)
         ):
             return False
-        else:
-            await self.won(ctx)
-            return True
+
+        await self.won(ctx)
+        return True
 
     async def reveal_one(
         self,
@@ -227,7 +226,7 @@ class Minesweeper(commands.Cog):
             await self.lost(ctx)
             revealed[y][x] = "x"  # mark bomb that made you lose with a x
             return True
-        elif board[y][x] == 0:
+        if board[y][x] == 0:
             self.reveal_zeros(revealed, board, x, y)
         return await self.check_if_won(ctx, revealed, board)
 
diff --git a/bot/exts/fun/movie.py b/bot/exts/fun/movie.py
index 422a83ac..3d36b119 100644
--- a/bot/exts/fun/movie.py
+++ b/bot/exts/fun/movie.py
@@ -22,7 +22,7 @@ THUMBNAIL_URL = "https://i.imgur.com/LtFtC8H.png"
 
 # Define movie params, that will be used for every movie request
 MOVIE_PARAMS = {
-    "api_key": Tokens.tmdb,
+    "api_key": Tokens.tmdb.get_secret_value(),
     "language": "en-US"
 }
 
@@ -63,17 +63,17 @@ class Movie(Cog):
     @group(name="movies", aliases=("movie",), invoke_without_command=True)
     async def movies(self, ctx: Context, genre: str = "", amount: int = 5) -> None:
         """
-        Get random movies by specifying genre. Also support amount parameter,\
-        that define how much movies will be shown.
+        Get random movies by specifying genre.
 
-        Default 5. Use .movies genres to get all available genres.
+        The amount parameter, that defines how many movies will be shown, defaults to 5.
+        Use `.movies genres` to get all available genres.
         """
         # Check is there more than 20 movies specified, due TMDB return 20 movies
         # per page, so this is max. Also you can't get less movies than 1, just logic
         if amount > 20:
             await ctx.send("You can't get more than 20 movies at once. (TMDB limits)")
             return
-        elif amount < 1:
+        if amount < 1:
             await ctx.send("You can't get less than 1 movie.")
             return
 
@@ -106,7 +106,7 @@ class Movie(Cog):
         """Return JSON of TMDB discover request."""
         # Define params of request
         params = {
-            "api_key": Tokens.tmdb,
+            "api_key": Tokens.tmdb.get_secret_value(),
             "language": "en-US",
             "sort_by": "popularity.desc",
             "include_adult": "false",
@@ -179,8 +179,8 @@ class Movie(Cog):
 
         text += "__**Some Numbers**__\n"
 
-        budget = f"{movie['budget']:,d}" if movie['budget'] else "?"
-        revenue = f"{movie['revenue']:,d}" if movie['revenue'] else "?"
+        budget = f"{movie['budget']:,d}" if movie["budget"] else "?"
+        revenue = f"{movie['revenue']:,d}" if movie["revenue"] else "?"
 
         if movie["runtime"] is not None:
             duration = divmod(movie["runtime"], 60)
@@ -208,4 +208,7 @@ class Movie(Cog):
 
 async def setup(bot: Bot) -> None:
     """Load the Movie Cog."""
+    if not Tokens.tmdb:
+        logger.warning("No TMDB token. Not loading Movie Cog.")
+        return
     await bot.add_cog(Movie(bot))
diff --git a/bot/exts/fun/quack.py b/bot/exts/fun/quack.py
index bb0cd731..9bb024fc 100644
--- a/bot/exts/fun/quack.py
+++ b/bot/exts/fun/quack.py
@@ -1,6 +1,6 @@
 import logging
 import random
-from typing import Literal, Optional
+from typing import Literal
 
 import discord
 from discord.ext import commands
@@ -8,7 +8,7 @@ from discord.ext import commands
 from bot.bot import Bot
 from bot.constants import Colours, NEGATIVE_REPLIES
 
-API_URL = 'https://quackstack.pythondiscord.com'
+API_URL = "https://quackstack.pythondiscord.com"
 
 log = logging.getLogger(__name__)
 
@@ -25,7 +25,7 @@ class Quackstack(commands.Cog):
         ctx: commands.Context,
         ducktype: Literal["duck", "manduck"] = "duck",
         *,
-        seed: Optional[str] = None
+        seed: str | None = None
     ) -> None:
         """
         Use the Quackstack API to generate a random duck.
diff --git a/bot/exts/fun/snakes/__init__.py b/bot/exts/fun/snakes/__init__.py
index 8aa39fb5..be71ac44 100644
--- a/bot/exts/fun/snakes/__init__.py
+++ b/bot/exts/fun/snakes/__init__.py
@@ -1,6 +1,7 @@
 import logging
 
 from bot.bot import Bot
+from bot.constants import Tokens
 from bot.exts.fun.snakes._snakes_cog import Snakes
 
 log = logging.getLogger(__name__)
@@ -8,4 +9,6 @@ log = logging.getLogger(__name__)
 
 async def setup(bot: Bot) -> None:
     """Load the Snakes Cog."""
+    if not Tokens.youtube:
+        log.warning("No Youtube token. All YouTube related commands in Snakes cog won't work.")
     await bot.add_cog(Snakes(bot))
diff --git a/bot/exts/fun/snakes/_snakes_cog.py b/bot/exts/fun/snakes/_snakes_cog.py
index d0542c23..eca462c6 100644
--- a/bot/exts/fun/snakes/_snakes_cog.py
+++ b/bot/exts/fun/snakes/_snakes_cog.py
@@ -9,7 +9,7 @@ import textwrap
 import urllib
 from functools import partial
 from io import BytesIO
-from typing import Any, Optional
+from typing import Any
 
 import async_timeout
 from PIL import Image, ImageDraw, ImageFont
@@ -274,7 +274,7 @@ class Snakes(Cog):
 
         return message
 
-    async def _fetch(self, url: str, params: Optional[dict] = None) -> dict:
+    async def _fetch(self, url: str, params: dict | None = None) -> dict:
         """Asynchronous web request helper method."""
         if params is None:
             params = {}
@@ -518,52 +518,51 @@ class Snakes(Cog):
                 log.debug("Antidote timed out waiting for a reaction")
                 break  # We're done, no reactions for the last 5 minutes
 
-            if antidote_tries < 10:
-                if antidote_guess_count < 4:
-                    if reaction.emoji in ANTIDOTE_EMOJI:
-                        antidote_guess_list.append(reaction.emoji)
-                        antidote_guess_count += 1
-
-                    if antidote_guess_count == 4:  # Guesses complete
-                        antidote_guess_count = 0
-                        page_guess_list[antidote_tries] = " ".join(antidote_guess_list)
-
-                        # Now check guess
-                        for i in range(0, len(antidote_answer)):
-                            if antidote_guess_list[i] == antidote_answer[i]:
-                                guess_result.append(TICK_EMOJI)
-                            elif antidote_guess_list[i] in antidote_answer:
-                                guess_result.append(BLANK_EMOJI)
-                            else:
-                                guess_result.append(CROSS_EMOJI)
-                        guess_result.sort()
-                        page_result_list[antidote_tries] = " ".join(guess_result)
-
-                        # Rebuild the board
-                        board = []
-                        for i in range(0, 10):
-                            board.append(f"`{i+1:02d}` "
-                                         f"{page_guess_list[i]} - "
-                                         f"{page_result_list[i]}")
-                            board.append(EMPTY_UNICODE)
-
-                        # Remove Reactions
-                        for emoji in antidote_guess_list:
-                            await board_id.remove_reaction(emoji, user)
-
-                        if antidote_guess_list == antidote_answer:
-                            win = True
-
-                        antidote_tries += 1
-                        guess_result = []
-                        antidote_guess_list = []
-
-                        antidote_embed.clear_fields()
-                        antidote_embed.add_field(name=f"{10 - antidote_tries} "
-                                                      f"guesses remaining",
-                                                 value="\n".join(board))
-                        # Redisplay the board
-                        await board_id.edit(embed=antidote_embed)
+            if antidote_tries < 10 and antidote_guess_count < 4:
+                if reaction.emoji in ANTIDOTE_EMOJI:
+                    antidote_guess_list.append(reaction.emoji)
+                    antidote_guess_count += 1
+
+                if antidote_guess_count == 4:  # Guesses complete
+                    antidote_guess_count = 0
+                    page_guess_list[antidote_tries] = " ".join(antidote_guess_list)
+
+                    # Now check guess
+                    for i in range(0, len(antidote_answer)):
+                        if antidote_guess_list[i] == antidote_answer[i]:
+                            guess_result.append(TICK_EMOJI)
+                        elif antidote_guess_list[i] in antidote_answer:
+                            guess_result.append(BLANK_EMOJI)
+                        else:
+                            guess_result.append(CROSS_EMOJI)
+                    guess_result.sort()
+                    page_result_list[antidote_tries] = " ".join(guess_result)
+
+                    # Rebuild the board
+                    board = []
+                    for i in range(0, 10):
+                        board.append(f"`{i+1:02d}` "
+                                     f"{page_guess_list[i]} - "
+                                     f"{page_result_list[i]}")
+                        board.append(EMPTY_UNICODE)
+
+                    # Remove Reactions
+                    for emoji in antidote_guess_list:
+                        await board_id.remove_reaction(emoji, user)
+
+                    if antidote_guess_list == antidote_answer:
+                        win = True
+
+                    antidote_tries += 1
+                    guess_result = []
+                    antidote_guess_list = []
+
+                    antidote_embed.clear_fields()
+                    antidote_embed.add_field(name=f"{10 - antidote_tries} "
+                                                  f"guesses remaining",
+                                             value="\n".join(board))
+                    # Redisplay the board
+                    await board_id.edit(embed=antidote_embed)
 
         # Winning / Ending Screen
         if win is True:
@@ -746,10 +745,10 @@ class Snakes(Cog):
         await message.delete()
 
         # Build and send the embed.
-        my_snake_embed = Embed(description=":tada: Congrats! You hatched: **{0}**".format(snake_name))
+        my_snake_embed = Embed(description=f":tada: Congrats! You hatched: **{snake_name}**")
         my_snake_embed.set_thumbnail(url=snake_image)
         my_snake_embed.set_footer(
-            text=" Owner: {0}#{1}".format(ctx.author.name, ctx.author.discriminator)
+            text=f" Owner: {ctx.author.name}#{ctx.author.discriminator}"
         )
 
         await ctx.send(embed=my_snake_embed)
@@ -773,7 +772,7 @@ class Snakes(Cog):
                     "query": "snake",
                     "page": page,
                     "language": "en-US",
-                    "api_key": Tokens.tmdb,
+                    "api_key": Tokens.tmdb.get_secret_value(),
                 }
             )
             data = await response.json()
@@ -785,7 +784,7 @@ class Snakes(Cog):
                 f"https://api.themoviedb.org/3/movie/{movie}",
                 params={
                     "language": "en-US",
-                    "api_key": Tokens.tmdb,
+                    "api_key": Tokens.tmdb.get_secret_value(),
                 }
             )
             data = await response.json()
@@ -832,7 +831,7 @@ class Snakes(Cog):
         # Prepare a question.
         question = random.choice(self.snake_quizzes)
         answer = question["answerkey"]
-        options = {key: question["options"][key] for key in ANSWERS_EMOJI.keys()}
+        options = {key: question["options"][key] for key in ANSWERS_EMOJI}
 
         # Build and send the embed.
         embed = Embed(
@@ -879,10 +878,7 @@ class Snakes(Cog):
             snake_name = snake_name.split()[-1]
 
         # If no name is provided, use whoever called the command.
-        if name:
-            user_name = name
-        else:
-            user_name = ctx.author.display_name
+        user_name = name if name else ctx.author.display_name
 
         # Get the index of the vowel to slice the username at
         user_slice_index = len(user_name)
@@ -1095,7 +1091,7 @@ class Snakes(Cog):
                 "part": "snippet",
                 "q": urllib.parse.quote_plus(query),
                 "type": "video",
-                "key": Tokens.youtube
+                "key": Tokens.youtube.get_secret_value()
             }
         )
         response = await response.json()
@@ -1148,3 +1144,4 @@ class Snakes(Cog):
             embed.description = "Could not generate the snake card! Please try again."
             embed.title = random.choice(ERROR_REPLIES)
             await ctx.send(embed=embed)
+    # endregion
diff --git a/bot/exts/fun/snakes/_utils.py b/bot/exts/fun/snakes/_utils.py
index 182fa9d9..ffffcd34 100644
--- a/bot/exts/fun/snakes/_utils.py
+++ b/bot/exts/fun/snakes/_utils.py
@@ -6,7 +6,6 @@ import math
 import random
 from itertools import product
 from pathlib import Path
-from typing import Union
 
 from PIL import Image
 from PIL.ImageDraw import ImageDraw
@@ -132,7 +131,7 @@ def lerp(t: float, a: float, b: float) -> float:
     return a + t * (b - a)
 
 
-class PerlinNoiseFactory(object):
+class PerlinNoiseFactory:
     """
     Callable that produces Perlin noise for an arbitrary point in an arbitrary number of dimensions.
 
@@ -396,7 +395,7 @@ class SnakeAndLaddersGame:
 
         Listen for reactions until players have joined, and the game has been started.
         """
-        def startup_event_check(reaction_: Reaction, user_: Union[User, Member]) -> bool:
+        def startup_event_check(reaction_: Reaction, user_: User | Member) -> bool:
             """Make sure that this reaction is what we want to operate on."""
             return (
                 all((
@@ -445,14 +444,12 @@ class SnakeAndLaddersGame:
                         # Allow game author or non-playing moderation staff to cancel a waiting game
                         await self.cancel_game()
                         return
-                    else:
-                        await self.player_leave(user)
-                elif reaction.emoji == START_EMOJI:
-                    if self.ctx.author == user:
-                        self.started = True
-                        await self.start_game(user)
-                        await startup.delete()
-                        break
+                    await self.player_leave(user)
+                elif reaction.emoji == START_EMOJI and self.ctx.author == user:
+                    self.started = True
+                    await self.start_game(user)
+                    await startup.delete()
+                    break
 
                 await startup.remove_reaction(reaction.emoji, user)
 
@@ -461,7 +458,7 @@ class SnakeAndLaddersGame:
                 await self.cancel_game()
                 return  # We're done, no reactions for the last 5 minutes
 
-    async def _add_player(self, user: Union[User, Member]) -> None:
+    async def _add_player(self, user: User | Member) -> None:
         """Add player to game."""
         self.players.append(user)
         self.player_tiles[user.id] = 1
@@ -470,7 +467,7 @@ class SnakeAndLaddersGame:
         im = Image.open(io.BytesIO(avatar_bytes)).resize((BOARD_PLAYER_SIZE, BOARD_PLAYER_SIZE))
         self.avatar_images[user.id] = im
 
-    async def player_join(self, user: Union[User, Member]) -> None:
+    async def player_join(self, user: User | Member) -> None:
         """
         Handle players joining the game.
 
@@ -492,11 +489,11 @@ class SnakeAndLaddersGame:
 
         await self.channel.send(
             f"**Snakes and Ladders**: {user.mention} has joined the game.\n"
-            f"There are now {str(len(self.players))} players in the game.",
+            f"There are now {len(self.players)!s} players in the game.",
             delete_after=10
         )
 
-    async def player_leave(self, user: Union[User, Member]) -> bool:
+    async def player_leave(self, user: User | Member) -> bool:
         """
         Handle players leaving the game.
 
@@ -531,17 +528,17 @@ class SnakeAndLaddersGame:
         await self.channel.send("**Snakes and Ladders**: Game has been canceled.")
         self._destruct()
 
-    async def start_game(self, user: Union[User, Member]) -> None:
+    async def start_game(self, user: User | Member) -> None:
         """
         Allow the game author to begin the game.
 
         The game cannot be started if the game is in a waiting state.
         """
-        if not user == self.author:
+        if user != self.author:
             await self.channel.send(user.mention + " Only the author of the game can start it.", delete_after=10)
             return
 
-        if not self.state == "waiting":
+        if self.state != "waiting":
             await self.channel.send(user.mention + " The game cannot be started at this time.", delete_after=10)
             return
 
@@ -552,7 +549,7 @@ class SnakeAndLaddersGame:
 
     async def start_round(self) -> None:
         """Begin the round."""
-        def game_event_check(reaction_: Reaction, user_: Union[User, Member]) -> bool:
+        def game_event_check(reaction_: Reaction, user_: User | Member) -> bool:
             """Make sure that this reaction is what we want to operate on."""
             return (
                 all((
@@ -626,8 +623,7 @@ class SnakeAndLaddersGame:
                         # Only allow non-playing moderation staff to cancel a running game
                         await self.cancel_game()
                         return
-                    else:
-                        is_surrendered = await self.player_leave(user)
+                    is_surrendered = await self.player_leave(user)
 
                 await self.positions.remove_reaction(reaction.emoji, user)
 
@@ -645,7 +641,7 @@ class SnakeAndLaddersGame:
         if not is_surrendered:
             await self._complete_round()
 
-    async def player_roll(self, user: Union[User, Member]) -> None:
+    async def player_roll(self, user: User | Member) -> None:
         """Handle the player's roll."""
         if user.id not in self.player_tiles:
             await self.channel.send(user.mention + " You are not in the match.", delete_after=10)
@@ -692,7 +688,7 @@ class SnakeAndLaddersGame:
         await self.channel.send("**Snakes and Ladders**: " + winner.mention + " has won the game! :tada:")
         self._destruct()
 
-    def _check_winner(self) -> Union[User, Member]:
+    def _check_winner(self) -> User | Member:
         """Return a winning member if we're in the post-round state and there's a winner."""
         if self.state != "post_round":
             return None
@@ -717,6 +713,6 @@ class SnakeAndLaddersGame:
         return x_level, y_level
 
     @staticmethod
-    def _is_moderator(user: Union[User, Member]) -> bool:
+    def _is_moderator(user: User | Member) -> bool:
         """Return True if the user is a Moderator."""
-        return any(role.id in MODERATION_ROLES for role in getattr(user, 'roles', []))
+        return any(role.id in MODERATION_ROLES for role in getattr(user, "roles", []))
diff --git a/bot/exts/fun/space.py b/bot/exts/fun/space.py
index 22a89050..3a666bfc 100644
--- a/bot/exts/fun/space.py
+++ b/bot/exts/fun/space.py
@@ -1,7 +1,7 @@
 import logging
 import random
-from datetime import date, datetime
-from typing import Any, Optional
+from datetime import UTC, date, datetime
+from typing import Any
 from urllib.parse import urlencode
 
 from discord import Embed
@@ -53,7 +53,7 @@ class Space(Cog):
         await self.bot.invoke_help_command(ctx)
 
     @space.command(name="apod")
-    async def apod(self, ctx: Context, date: Optional[str]) -> None:
+    async def apod(self, ctx: Context, date: str | None) -> None:
         """
         Get Astronomy Picture of Day from NASA API. Date is optional parameter, what formatting is YYYY-MM-DD.
 
@@ -63,13 +63,13 @@ class Space(Cog):
         # Parse date to params, when provided. Show error message when invalid formatting
         if date:
             try:
-                apod_date = datetime.strptime(date, "%Y-%m-%d").date()
+                apod_date = datetime.strptime(date, "%Y-%m-%d").replace(tzinfo=UTC).date()
             except ValueError:
                 await ctx.send(f"Invalid date {date}. Please make sure your date is in format YYYY-MM-DD.")
                 return
 
-            now = datetime.now().date()
-            if APOD_MIN_DATE > apod_date or now < apod_date:
+            now = datetime.now(tz=UTC).date()
+            if apod_date < APOD_MIN_DATE or now < apod_date:
                 await ctx.send(f"Date must be between {APOD_MIN_DATE.isoformat()} and {now.isoformat()} (today).")
                 return
 
@@ -86,7 +86,7 @@ class Space(Cog):
         )
 
     @space.command(name="nasa")
-    async def nasa(self, ctx: Context, *, search_term: Optional[str]) -> None:
+    async def nasa(self, ctx: Context, *, search_term: str | None) -> None:
         """Get random NASA information/facts + image. Support `search_term` parameter for more specific search."""
         params = {
             "media_type": "image"
@@ -111,11 +111,11 @@ class Space(Cog):
         )
 
     @space.command(name="epic")
-    async def epic(self, ctx: Context, date: Optional[str]) -> None:
+    async def epic(self, ctx: Context, date: str | None) -> None:
         """Get a random image of the Earth from the NASA EPIC API. Support date parameter, format is YYYY-MM-DD."""
         if date:
             try:
-                show_date = datetime.strptime(date, "%Y-%m-%d").date().isoformat()
+                show_date = datetime.strptime(date, "%Y-%m-%d").replace(tzinfo=UTC).date().isoformat()
             except ValueError:
                 await ctx.send(f"Invalid date {date}. Please make sure your date is in format YYYY-MM-DD.")
                 return
@@ -147,7 +147,7 @@ class Space(Cog):
     async def mars(
         self,
         ctx: Context,
-        date: Optional[DateConverter],
+        date: DateConverter | None,
         rover: str = "curiosity"
     ) -> None:
         """
@@ -158,10 +158,8 @@ class Space(Cog):
         rover = rover.lower()
         if rover not in self.rovers:
             await ctx.send(
-                (
-                    f"Invalid rover `{rover}`.\n"
-                    f"**Rovers:** `{'`, `'.join(f'{r.capitalize()}' for r in self.rovers)}`"
-                )
+                f"Invalid rover `{rover}`.\n"
+                f"**Rovers:** `{'`, `'.join(f'{r.capitalize()}' for r in self.rovers)}`"
             )
             return
 
@@ -203,14 +201,14 @@ class Space(Cog):
     async def fetch_from_nasa(
         self,
         endpoint: str,
-        additional_params: Optional[dict[str, Any]] = None,
-        base: Optional[str] = NASA_BASE_URL,
+        additional_params: dict[str, Any] | None = None,
+        base: str | None = NASA_BASE_URL,
         use_api_key: bool = True
     ) -> dict[str, Any]:
         """Fetch information from NASA API, return result."""
         params = {}
         if use_api_key:
-            params["api_key"] = Tokens.nasa
+            params["api_key"] = Tokens.nasa.get_secret_value()
 
         # Add additional parameters to request parameters only when they provided by user
         if additional_params is not None:
@@ -219,7 +217,7 @@ class Space(Cog):
         async with self.http_session.get(url=f"{base}/{endpoint}?{urlencode(params)}") as resp:
             return await resp.json()
 
-    def create_nasa_embed(self, title: str, description: str, image: str, footer: Optional[str] = "") -> Embed:
+    def create_nasa_embed(self, title: str, description: str, image: str, footer: str | None = "") -> Embed:
         """Generate NASA commands embeds. Required: title, description and image URL, footer (addition) is optional."""
         return Embed(
             title=title,
diff --git a/bot/exts/fun/tic_tac_toe.py b/bot/exts/fun/tic_tac_toe.py
index fa2a7531..d4ae7107 100644
--- a/bot/exts/fun/tic_tac_toe.py
+++ b/bot/exts/fun/tic_tac_toe.py
@@ -1,6 +1,6 @@
 import asyncio
 import random
-from typing import Callable, Optional, Union
+from collections.abc import Callable
 
 import discord
 from discord.ext.commands import Cog, Context, check, group
@@ -42,7 +42,7 @@ class Player:
         self.ctx = ctx
         self.symbol = symbol
 
-    async def get_move(self, board: dict[int, str], msg: discord.Message) -> tuple[bool, Optional[int]]:
+    async def get_move(self, board: dict[int, str], msg: discord.Message) -> tuple[bool, int | None]:
         """
         Get move from user.
 
@@ -106,7 +106,7 @@ class AI:
 class Game:
     """Class that contains information and functions about Tic Tac Toe game."""
 
-    def __init__(self, players: list[Union[Player, AI]], ctx: Context):
+    def __init__(self, players: list[Player | AI], ctx: Context):
         self.players = players
         self.ctx = ctx
         self.channel = ctx.channel
@@ -125,13 +125,13 @@ class Game:
         self.current = self.players[0]
         self.next = self.players[1]
 
-        self.winner: Optional[Union[Player, AI]] = None
-        self.loser: Optional[Union[Player, AI]] = None
+        self.winner: Player | AI | None = None
+        self.loser: Player | AI | None = None
         self.over = False
         self.canceled = False
         self.draw = False
 
-    async def get_confirmation(self) -> tuple[bool, Optional[str]]:
+    async def get_confirmation(self) -> tuple[bool, str | None]:
         """
         Ask does user want to play TicTacToe against requester. First player is always requester.
 
@@ -171,10 +171,10 @@ class Game:
         await confirm_message.delete()
         if reaction.emoji == Emojis.confirmation:
             return True, None
-        else:
-            self.over = True
-            self.canceled = True
-            return False, "User declined"
+
+        self.over = True
+        self.canceled = True
+        return False, "User declined"
 
     @staticmethod
     async def add_reactions(msg: discord.Message) -> None:
@@ -186,7 +186,8 @@ class Game:
         """Get formatted tic-tac-toe board for message."""
         board = list(self.board.values())
         return "\n".join(
-            (f"{board[line]} {board[line + 1]} {board[line + 2]}" for line in range(0, len(board), 3))
+            f"{board[line]} {board[line + 1]} {board[line + 2]}"
+            for line in range(0, len(board), 3)
         )
 
     async def play(self) -> None:
@@ -256,7 +257,7 @@ class TicTacToe(Cog):
     @is_channel_free()
     @is_requester_free()
     @group(name="tictactoe", aliases=("ttt", "tic"), invoke_without_command=True)
-    async def tic_tac_toe(self, ctx: Context, opponent: Optional[discord.User]) -> None:
+    async def tic_tac_toe(self, ctx: Context, opponent: discord.User | None) -> None:
         """Tic Tac Toe game. Play against friends or AI. Use reactions to add your mark to field."""
         if opponent == ctx.author:
             await ctx.send("You can't play against yourself.")
diff --git a/bot/exts/fun/trivia_quiz.py b/bot/exts/fun/trivia_quiz.py
index 31652374..28cd4657 100644
--- a/bot/exts/fun/trivia_quiz.py
+++ b/bot/exts/fun/trivia_quiz.py
@@ -6,10 +6,10 @@ import random
 import re
 import string
 from collections import defaultdict
+from collections.abc import Callable
 from dataclasses import dataclass
-from datetime import datetime, timedelta
+from datetime import UTC, datetime, timedelta
 from pathlib import Path
-from typing import Callable, Optional
 
 import discord
 from discord.ext import commands, tasks
@@ -249,7 +249,7 @@ class TriviaQuiz(commands.Cog):
         wiki_questions = []
         # trivia_quiz.json follows a pattern, every new category starts with the next century.
         start_id = 501
-        yesterday = datetime.strftime(datetime.now() - timedelta(1), '%Y/%m/%d')
+        yesterday = datetime.strftime(datetime.now(tz=UTC) - timedelta(1), "%Y/%m/%d")
 
         while error_fetches < MAX_ERROR_FETCH_TRIES:
             async with self.bot.http_session.get(url=WIKI_FEED_API_URL.format(date=yesterday)) as r:
@@ -267,7 +267,7 @@ class TriviaQuiz(commands.Cog):
                     # Normalize the wikipedia article title to remove all punctuations from it
                     for word in re.split(r"[\s-]", title := article["normalizedtitle"]):
                         cleaned_title = re.sub(
-                            rf'\b{word.strip(string.punctuation)}\b', word, title, flags=re.IGNORECASE
+                            rf"\b{word.strip(string.punctuation)}\b", word, title, flags=re.IGNORECASE
                         )
 
                     # Since the extract contains the article name sometimes this would replace all the matching words
@@ -279,7 +279,7 @@ class TriviaQuiz(commands.Cog):
                     for word in re.split(r"[\s-]", cleaned_title):
                         word = word.strip(string.punctuation)
                         secret_word = r"\*" * len(word)
-                        question = re.sub(rf'\b{word}\b', f"**{secret_word}**", question, flags=re.IGNORECASE)
+                        question = re.sub(rf"\b{word}\b", f"**{secret_word}**", question, flags=re.IGNORECASE)
 
                     formatted_article_question = {
                         "id": start_id,
@@ -307,7 +307,7 @@ class TriviaQuiz(commands.Cog):
         return json.loads(p.read_text(encoding="utf-8"))
 
     @commands.group(name="quiz", aliases=("trivia", "triviaquiz"), invoke_without_command=True)
-    async def quiz_game(self, ctx: commands.Context, category: Optional[str], questions: Optional[int]) -> None:
+    async def quiz_game(self, ctx: commands.Context, category: str | None, questions: int | None) -> None:
         """
         Start a quiz!
 
@@ -550,7 +550,7 @@ class TriviaQuiz(commands.Cog):
             if self.game_status[ctx.channel.id]:
                 # Check if the author is the game starter or a moderator.
                 if ctx.author == self.game_owners[ctx.channel.id] or any(
-                    role.id in MODERATION_ROLES for role in getattr(ctx.author, 'roles', [])
+                    role.id in MODERATION_ROLES for role in getattr(ctx.author, "roles", [])
                 ):
                     self.game_status[ctx.channel.id] = False
                     del self.game_owners[ctx.channel.id]
diff --git a/bot/exts/fun/uwu.py b/bot/exts/fun/uwu.py
index 7a9d55d0..488c68f3 100644
--- a/bot/exts/fun/uwu.py
+++ b/bot/exts/fun/uwu.py
@@ -30,7 +30,7 @@ EMOJIS = [
     "o.O",
     "-.-",
     ">w<",
-    "σωσ",
+    "σωσ",  # noqa: RUF001
     "òωó",
     "ʘwʘ",
     ":3",
@@ -74,7 +74,7 @@ class Emoji:
         return bot.get_emoji(self.uid) is not None
 
     @classmethod
-    def from_match(cls, match: tuple[str, str, str]) -> t.Optional['Emoji']:
+    def from_match(cls, match: tuple[str, str, str]) -> t.Optional["Emoji"]:
         """Creates an Emoji from a regex match tuple."""
         if not match or len(match) != 3 or not match[2].isdecimal():
             return None
@@ -155,7 +155,7 @@ class Uwu(Cog):
         return input_string
 
     @commands.command(name="uwu", aliases=("uwuwize", "uwuify",))
-    async def uwu_command(self, ctx: Context, *, text: t.Optional[str] = None) -> None:
+    async def uwu_command(self, ctx: Context, *, text: str | None = None) -> None:
         """
         Echo an uwuified version the passed text.
 
diff --git a/bot/exts/fun/wonder_twins.py b/bot/exts/fun/wonder_twins.py
index 0c5b0a76..9385780d 100644
--- a/bot/exts/fun/wonder_twins.py
+++ b/bot/exts/fun/wonder_twins.py
@@ -11,8 +11,8 @@ class WonderTwins(Cog):
     """Cog for a Wonder Twins inspired command."""
 
     def __init__(self):
-        with open(Path.cwd() / "bot" / "resources" / "fun" / "wonder_twins.yaml", "r", encoding="utf-8") as f:
-            info = yaml.load(f, Loader=yaml.FullLoader)
+        with open(Path.cwd() / "bot" / "resources" / "fun" / "wonder_twins.yaml", encoding="utf-8") as f:
+            info = yaml.safe_load(f)
             self.water_types = info["water_types"]
             self.objects = info["objects"]
             self.adjectives = info["adjectives"]
diff --git a/bot/exts/fun/xkcd.py b/bot/exts/fun/xkcd.py
index 380c3c80..7b34795c 100644
--- a/bot/exts/fun/xkcd.py
+++ b/bot/exts/fun/xkcd.py
@@ -1,7 +1,6 @@
 import logging
 import re
 from random import randint
-from typing import Optional, Union
 
 from discord import Embed
 from discord.ext import tasks
@@ -21,7 +20,7 @@ class XKCD(Cog):
 
     def __init__(self, bot: Bot):
         self.bot = bot
-        self.latest_comic_info: dict[str, Union[str, int]] = {}
+        self.latest_comic_info: dict[str, str | int] = {}
         self.get_latest_comic_info.start()
 
     def cog_unload(self) -> None:
@@ -38,7 +37,7 @@ class XKCD(Cog):
                 log.debug(f"Failed to get latest XKCD comic information. Status code {resp.status}")
 
     @command(name="xkcd")
-    async def fetch_xkcd_comics(self, ctx: Context, comic: Optional[str]) -> None:
+    async def fetch_xkcd_comics(self, ctx: Context, comic: str | None) -> None:
         """
         Getting an xkcd comic's information along with the image.
 
diff --git a/bot/exts/holidays/easter/bunny_name_generator.py b/bot/exts/holidays/easter/bunny_name_generator.py
index 50872ebc..3034da4a 100644
--- a/bot/exts/holidays/easter/bunny_name_generator.py
+++ b/bot/exts/holidays/easter/bunny_name_generator.py
@@ -3,7 +3,6 @@ import logging
 import random
 import re
 from pathlib import Path
-from typing import Optional
 
 from discord.ext import commands
 
@@ -18,7 +17,7 @@ class BunnyNameGenerator(commands.Cog):
     """Generate a random bunny name, or bunnify your Discord username!"""
 
     @staticmethod
-    def find_separators(displayname: str) -> Optional[list[str]]:
+    def find_separators(displayname: str) -> list[str] | None:
         """Check if Discord name contains spaces so we can bunnify an individual word in the name."""
         new_name = re.split(r"[_.\s]", displayname)
         if displayname not in new_name:
@@ -26,7 +25,7 @@ class BunnyNameGenerator(commands.Cog):
         return None
 
     @staticmethod
-    def find_vowels(displayname: str) -> Optional[str]:
+    def find_vowels(displayname: str) -> str | None:
         """
         Finds vowels in the user's display name.
 
@@ -46,6 +45,7 @@ class BunnyNameGenerator(commands.Cog):
             new_name = re.sub(exp, vowel_sub, displayname)
             if new_name != displayname:
                 return new_name
+        return None
 
     @staticmethod
     def append_name(displayname: str) -> str:
@@ -77,7 +77,7 @@ class BunnyNameGenerator(commands.Cog):
         unmatched_name = self.append_name(username)
 
         if spaces_in_name is not None:
-            replacements = ["Cotton", "Fluff", "Floof" "Bounce", "Snuffle", "Nibble", "Cuddle", "Velvetpaw", "Carrot"]
+            replacements = ["Cotton", "Fluff", "Floof", "Bounce", "Snuffle", "Nibble", "Cuddle", "Velvetpaw", "Carrot"]
             word_to_replace = random.choice(spaces_in_name)
             substitute = random.choice(replacements)
             bunnified_name = username.replace(word_to_replace, substitute)
diff --git a/bot/exts/holidays/easter/earth_photos.py b/bot/exts/holidays/easter/earth_photos.py
index e60e2626..66f1b07b 100644
--- a/bot/exts/holidays/easter/earth_photos.py
+++ b/bot/exts/holidays/easter/earth_photos.py
@@ -12,7 +12,7 @@ API_URL = "https://api.unsplash.com/photos/random"
 
 
 class EarthPhotos(commands.Cog):
-    """This cog contains the command for earth photos."""
+    """The earth photos cog."""
 
     def __init__(self, bot: Bot):
         self.bot = bot
@@ -23,7 +23,7 @@ class EarthPhotos(commands.Cog):
         async with ctx.typing():
             async with self.bot.http_session.get(
                     API_URL,
-                    params={"query": "planet_earth", "client_id": Tokens.unsplash_access_key}
+                    params={"query": "planet_earth", "client_id": Tokens.unsplash.get_secret_value()}
             ) as r:
                 jsondata = await r.json()
                 linksdata = jsondata.get("urls")
@@ -37,7 +37,7 @@ class EarthPhotos(commands.Cog):
                 rf = "?utm_source=Sir%20Lancebot&utm_medium=referral"
             async with self.bot.http_session.get(
                 downloadlinksdata.get("download_location"),
-                    params={"client_id": Tokens.unsplash_access_key}
+                    params={"client_id": Tokens.unsplash.get_secret_value()}
             ) as _:
                 pass
 
@@ -59,7 +59,7 @@ class EarthPhotos(commands.Cog):
 
 async def setup(bot: Bot) -> None:
     """Load the Earth Photos cog."""
-    if not Tokens.unsplash_access_key:
+    if not Tokens.unsplash:
         log.warning("No Unsplash access key found. Cog not loading.")
         return
     await bot.add_cog(EarthPhotos(bot))
diff --git a/bot/exts/holidays/easter/easter_riddle.py b/bot/exts/holidays/easter/easter_riddle.py
index c5d7b164..6c29dd17 100644
--- a/bot/exts/holidays/easter/easter_riddle.py
+++ b/bot/exts/holidays/easter/easter_riddle.py
@@ -18,7 +18,7 @@ TIMELIMIT = 10
 
 
 class EasterRiddle(commands.Cog):
-    """This cog contains the command for the Easter quiz!"""
+    """The Easter quiz cog."""
 
     def __init__(self, bot: Bot):
         self.bot = bot
diff --git a/bot/exts/holidays/easter/egg_decorating.py b/bot/exts/holidays/easter/egg_decorating.py
index a9334820..1327f4d0 100644
--- a/bot/exts/holidays/easter/egg_decorating.py
+++ b/bot/exts/holidays/easter/egg_decorating.py
@@ -4,7 +4,6 @@ import random
 from contextlib import suppress
 from io import BytesIO
 from pathlib import Path
-from typing import Optional, Union
 
 import discord
 from PIL import Image
@@ -33,7 +32,7 @@ class EggDecorating(commands.Cog):
     """Decorate some easter eggs!"""
 
     @staticmethod
-    def replace_invalid(colour: str) -> Optional[int]:
+    def replace_invalid(colour: str) -> int | None:
         """Attempts to match with HTML or XKCD colour names, returning the int value."""
         with suppress(KeyError):
             return int(HTML_COLOURS[colour], 16)
@@ -43,8 +42,8 @@ class EggDecorating(commands.Cog):
 
     @commands.command(aliases=("decorateegg",))
     async def eggdecorate(
-        self, ctx: commands.Context, *colours: Union[discord.Colour, str]
-    ) -> Optional[Image.Image]:
+        self, ctx: commands.Context, *colours: discord.Colour | str
+    ) -> Image.Image | None:
         """
         Picks a random egg design and decorates it using the given colours.
 
@@ -53,7 +52,7 @@ class EggDecorating(commands.Cog):
         """
         if len(colours) < 2:
             await ctx.send("You must include at least 2 colours!")
-            return
+            return None
 
         invalid = []
         colours = list(colours)
@@ -68,10 +67,10 @@ class EggDecorating(commands.Cog):
 
         if len(invalid) > 1:
             await ctx.send(f"Sorry, I don't know these colours: {' '.join(invalid)}")
-            return
-        elif len(invalid) == 1:
+            return None
+        if len(invalid) == 1:
             await ctx.send(f"Sorry, I don't know the colour {invalid[0]}!")
-            return
+            return None
 
         async with ctx.typing():
             # Expand list to 8 colours
diff --git a/bot/exts/holidays/easter/egghead_quiz.py b/bot/exts/holidays/easter/egghead_quiz.py
index 2e4d1931..046f9fac 100644
--- a/bot/exts/holidays/easter/egghead_quiz.py
+++ b/bot/exts/holidays/easter/egghead_quiz.py
@@ -3,7 +3,6 @@ import logging
 import random
 from json import loads
 from pathlib import Path
-from typing import Union
 
 import discord
 from discord.ext import commands
@@ -29,7 +28,7 @@ TIMELIMIT = 30
 
 
 class EggheadQuiz(commands.Cog):
-    """This cog contains the command for the Easter quiz!"""
+    """The Egghead quiz cog."""
 
     def __init__(self):
         self.quiz_messages = {}
@@ -117,9 +116,10 @@ class EggheadQuiz(commands.Cog):
         )
 
         await ctx.send(content, embed=a_embed)
+        return None
 
     @staticmethod
-    async def already_reacted(new_reaction: discord.Reaction, user: Union[discord.Member, discord.User]) -> bool:
+    async def already_reacted(new_reaction: discord.Reaction, user: discord.Member | discord.User) -> bool:
         """Returns whether a given user has reacted more than once to a given message."""
         message = new_reaction.message
         for reaction in message.reactions:
@@ -131,16 +131,17 @@ class EggheadQuiz(commands.Cog):
         return False
 
     @commands.Cog.listener()
-    async def on_reaction_add(self, reaction: discord.Reaction, user: Union[discord.Member, discord.User]) -> None:
+    async def on_reaction_add(self, reaction: discord.Reaction, user: discord.Member | discord.User) -> None:
         """Listener to listen specifically for reactions of quiz messages."""
         if user.bot:
-            return
+            return None
         if reaction.message.id not in self.quiz_messages:
-            return
+            return None
         if str(reaction.emoji) not in self.quiz_messages[reaction.message.id]:
             return await reaction.message.remove_reaction(reaction, user)
         if await self.already_reacted(reaction, user):
             return await reaction.message.remove_reaction(reaction, user)
+        return None
 
 
 async def setup(bot: Bot) -> None:
diff --git a/bot/exts/holidays/halloween/candy_collection.py b/bot/exts/holidays/halloween/candy_collection.py
index 683114f9..ca68888b 100644
--- a/bot/exts/holidays/halloween/candy_collection.py
+++ b/bot/exts/holidays/halloween/candy_collection.py
@@ -1,6 +1,5 @@
 import logging
 import random
-from typing import Union
 
 import discord
 from async_rediscache import RedisCache
@@ -18,17 +17,17 @@ ADD_CANDY_EXISTING_REACTION_CHANCE = 10  # 10%
 ADD_SKULL_REACTION_CHANCE = 50  # 2%
 ADD_SKULL_EXISTING_REACTION_CHANCE = 20  # 5%
 
-EMOJIS = dict(
-    CANDY="\N{CANDY}",
-    SKULL="\N{SKULL}",
-    MEDALS=(
+EMOJIS = {
+    "CANDY": "\N{CANDY}",
+    "SKULL": "\N{SKULL}",
+    "MEDALS": (
         "\N{FIRST PLACE MEDAL}",
         "\N{SECOND PLACE MEDAL}",
         "\N{THIRD PLACE MEDAL}",
         "\N{SPORTS MEDAL}",
         "\N{SPORTS MEDAL}",
     ),
-)
+}
 
 
 class CandyCollection(commands.Cog):
@@ -69,7 +68,7 @@ class CandyCollection(commands.Cog):
 
     @in_month(Month.OCTOBER)
     @commands.Cog.listener()
-    async def on_reaction_add(self, reaction: discord.Reaction, user: Union[discord.User, discord.Member]) -> None:
+    async def on_reaction_add(self, reaction: discord.Reaction, user: discord.User | discord.Member) -> None:
         """Add/remove candies from a person if the reaction satisfies criteria."""
         message = reaction.message
         # check to ensure the reactor is human
@@ -140,7 +139,7 @@ class CandyCollection(commands.Cog):
 
     @staticmethod
     async def send_spook_msg(
-        author: discord.Member, channel: discord.TextChannel, candies: Union[str, int]
+        author: discord.Member, channel: discord.TextChannel, candies: str | int
     ) -> None:
         """Send a spooky message."""
         e = discord.Embed(colour=author.colour)
diff --git a/bot/exts/holidays/halloween/8ball.py b/bot/exts/holidays/halloween/eight_ball.py
index 21b55a01..21b55a01 100644
--- a/bot/exts/holidays/halloween/8ball.py
+++ b/bot/exts/holidays/halloween/eight_ball.py
diff --git a/bot/exts/holidays/halloween/monstersurvey.py b/bot/exts/holidays/halloween/monstersurvey.py
index 517f1bcb..d129f3cc 100644
--- a/bot/exts/holidays/halloween/monstersurvey.py
+++ b/bot/exts/holidays/halloween/monstersurvey.py
@@ -9,8 +9,8 @@ from discord.ext.commands import Bot, Cog, Context
 log = logging.getLogger(__name__)
 
 EMOJIS = {
-    "SUCCESS": u"\u2705",
-    "ERROR": u"\u274C"
+    "SUCCESS": "\u2705",
+    "ERROR": "\u274C"
 }
 
 
diff --git a/bot/exts/holidays/halloween/scarymovie.py b/bot/exts/holidays/halloween/scarymovie.py
index 9f1a95fd..fbab3dd2 100644
--- a/bot/exts/holidays/halloween/scarymovie.py
+++ b/bot/exts/holidays/halloween/scarymovie.py
@@ -36,7 +36,7 @@ class ScaryMovie(commands.Cog):
         """Selects a random movie and returns a JSON of movie details from TMDb."""
         url = "https://api.themoviedb.org/3/discover/movie"
         params = {
-            "api_key": Tokens.tmdb,
+            "api_key": Tokens.tmdb.get_secret_value(),
             "with_genres": "27",
             "vote_count.gte": "5",
             "include_adult": "false"
@@ -65,7 +65,7 @@ class ScaryMovie(commands.Cog):
         # Get full details and credits
         async with self.bot.http_session.get(
             url=f"https://api.themoviedb.org/3/movie/{selection_id}",
-            params={"api_key": Tokens.tmdb, "append_to_response": "credits"}
+            params={"api_key": Tokens.tmdb.get_secret_value(), "append_to_response": "credits"}
         ) as selection:
 
             return await selection.json()
@@ -135,4 +135,7 @@ class ScaryMovie(commands.Cog):
 
 async def setup(bot: Bot) -> None:
     """Load the Scary Movie Cog."""
+    if not Tokens.tmdb:
+        log.warning("No TMDB Token. Not loading ScaryMovie Cog.")
+        return
     await bot.add_cog(ScaryMovie(bot))
diff --git a/bot/exts/holidays/halloween/spookygif.py b/bot/exts/holidays/halloween/spookygif.py
index 750e86ca..b3f9d703 100644
--- a/bot/exts/holidays/halloween/spookygif.py
+++ b/bot/exts/holidays/halloween/spookygif.py
@@ -21,7 +21,7 @@ class SpookyGif(commands.Cog):
     async def spookygif(self, ctx: commands.Context) -> None:
         """Fetches a random gif from the GIPHY API and responds with it."""
         async with ctx.typing():
-            params = {"api_key": Tokens.giphy, "tag": "halloween", "rating": "g"}
+            params = {"api_key": Tokens.giphy.get_secret_value(), "tag": "halloween", "rating": "g"}
             # Make a GET request to the Giphy API to get a random halloween gif.
             async with self.bot.http_session.get(API_URL, params=params) as resp:
                 data = await resp.json()
@@ -35,4 +35,7 @@ class SpookyGif(commands.Cog):
 
 async def setup(bot: Bot) -> None:
     """Spooky GIF Cog load."""
+    if not Tokens.giphy:
+        log.warning("No Giphy token. Not loading SpookyGif cog.")
+        return
     await bot.add_cog(SpookyGif(bot))
diff --git a/bot/exts/holidays/halloween/spookynamerate.py b/bot/exts/holidays/halloween/spookynamerate.py
index a76e5e12..78e8be8e 100644
--- a/bot/exts/holidays/halloween/spookynamerate.py
+++ b/bot/exts/holidays/halloween/spookynamerate.py
@@ -2,11 +2,10 @@ import asyncio
 import json
 import random
 from collections import defaultdict
-from datetime import datetime, timedelta
+from datetime import UTC, datetime, timedelta
 from logging import getLogger
 from os import getenv
 from pathlib import Path
-from typing import Optional
 
 from async_rediscache import RedisCache
 from discord import Embed, Reaction, TextChannel, User
@@ -146,7 +145,7 @@ class SpookyNameRate(Cog):
                 )
                 return
 
-            elif data["name"] == name:
+            if data["name"] == name:
                 await ctx.send("TOO LATE. Someone has already added this name.")
                 return
 
@@ -261,12 +260,8 @@ class SpookyNameRate(Cog):
             winners = []
             for i, winner in enumerate(winner_messages):
                 winners.append(winner)
-                if len(winner_messages) > i + 1:
-                    if winner_messages[i + 1][1]["score"] != winner[1]["score"]:
-                        break
-                elif len(winner_messages) == (i + 1) + 1:  # The next element is the last element
-                    if winner_messages[i + 1][1]["score"] != winner[1]["score"]:
-                        break
+                if len(winner_messages) > i + 1 and winner_messages[i + 1][1]["score"] != winner[1]["score"]:
+                    break
 
             # one iteration is complete
             await channel.send("Today's Spooky Name Rate Game ends now, and the winner(s) is(are)...")
@@ -313,7 +308,7 @@ class SpookyNameRate(Cog):
         if SpookyNameRate.debug:
             return
 
-        now = datetime.utcnow()
+        now = datetime.now(tz=UTC)
         if now.hour < 12:
             twelve_pm = now.replace(hour=12, minute=0, second=0, microsecond=0)
             time_left = twelve_pm - now
@@ -353,7 +348,7 @@ class SpookyNameRate(Cog):
 
         return embed
 
-    async def get_channel(self) -> Optional[TextChannel]:
+    async def get_channel(self) -> TextChannel | None:
         """Gets the sir-lancebot-channel after waiting until ready."""
         channel = self.bot.get_channel(
             Channels.sir_lancebot_playground
@@ -369,7 +364,7 @@ class SpookyNameRate(Cog):
             return True
 
         if not Client.month_override:
-            return datetime.utcnow().month == Month.OCTOBER
+            return datetime.now(tz=UTC).month == Month.OCTOBER
         return Client.month_override == Month.OCTOBER
 
     def cog_check(self, ctx: Context) -> bool:
diff --git a/bot/exts/holidays/hanukkah/hanukkah_embed.py b/bot/exts/holidays/hanukkah/hanukkah_embed.py
index 1ebc21e8..fd8edca1 100644
--- a/bot/exts/holidays/hanukkah/hanukkah_embed.py
+++ b/bot/exts/holidays/hanukkah/hanukkah_embed.py
@@ -1,5 +1,5 @@
-import datetime
 import logging
+from datetime import UTC, date, datetime
 
 from discord import Embed
 from discord.ext import commands
@@ -21,18 +21,18 @@ class HanukkahEmbed(commands.Cog):
 
     def __init__(self, bot: Bot):
         self.bot = bot
-        self.hanukkah_dates: list[datetime.date] = []
+        self.hanukkah_dates: list[date] = []
 
-    def _parse_time_to_datetime(self, date: list[str]) -> datetime.datetime:
+    def _parse_time_to_datetime(self, date: list[str]) -> datetime:
         """Format the times provided by the api to datetime forms."""
         try:
-            return datetime.datetime.strptime(date, "%Y-%m-%dT%H:%M:%S%z")
+            return datetime.strptime(date, "%Y-%m-%dT%H:%M:%S%z")
         except ValueError:
             # there is a possibility of an event not having a time, just a day
             # to catch this, we try again without time information
-            return datetime.datetime.strptime(date, "%Y-%m-%d")
+            return datetime.strptime(date, "%Y-%m-%d").replace(tzinfo=UTC)
 
-    async def fetch_hanukkah_dates(self) -> list[datetime.date]:
+    async def fetch_hanukkah_dates(self) -> list[date]:
         """Gets the dates for hanukkah festival."""
         # clear the datetime objects to prevent a memory link
         self.hanukkah_dates = []
@@ -52,11 +52,11 @@ class HanukkahEmbed(commands.Cog):
         hanukkah_dates = await self.fetch_hanukkah_dates()
         start_day = hanukkah_dates[0]
         end_day = hanukkah_dates[-1]
-        today = datetime.date.today()
+        today = datetime.now(tz=UTC).date()
         embed = Embed(title="Hanukkah", colour=Colours.blue)
         if start_day <= today <= end_day:
             if start_day == today:
-                now = datetime.datetime.utcnow()
+                now = datetime.now(tz=UTC)
                 hours = now.hour + 4  # using only hours
                 hanukkah_start_hour = 18
                 if hours < hanukkah_start_hour:
@@ -66,7 +66,8 @@ class HanukkahEmbed(commands.Cog):
                     )
                     await ctx.send(embed=embed)
                     return
-                elif hours > hanukkah_start_hour:
+
+                if hours > hanukkah_start_hour:
                     embed.description = (
                         "It is the starting day of Hanukkah! "
                         f"Its been {hours - hanukkah_start_hour} hours hanukkah started!"
diff --git a/bot/exts/holidays/holidayreact.py b/bot/exts/holidays/holidayreact.py
index ee20b792..c3686fab 100644
--- a/bot/exts/holidays/holidayreact.py
+++ b/bot/exts/holidays/holidayreact.py
@@ -72,9 +72,9 @@ HOLIDAYS_TO_REACT = [
     Valentines, Easter, EarthDay, Pride, Halloween, Hanukkah, Christmas
 ]
 # Type (or order) doesn't matter here - set is for de-duplication
-MONTHS_TO_REACT = set(
+MONTHS_TO_REACT = {
     month for holiday in HOLIDAYS_TO_REACT for month in holiday.months
-)
+}
 
 
 class HolidayReact(Cog):
diff --git a/bot/exts/holidays/pride/pride_anthem.py b/bot/exts/holidays/pride/pride_anthem.py
index 6b78cba1..c719e388 100644
--- a/bot/exts/holidays/pride/pride_anthem.py
+++ b/bot/exts/holidays/pride/pride_anthem.py
@@ -2,7 +2,6 @@ import json
 import logging
 import random
 from pathlib import Path
-from typing import Optional
 
 from discord.ext import commands
 
@@ -16,7 +15,7 @@ VIDEOS = json.loads(Path("bot/resources/holidays/pride/anthems.json").read_text(
 class PrideAnthem(commands.Cog):
     """Embed a random youtube video for a gay anthem!"""
 
-    def get_video(self, genre: Optional[str] = None) -> dict:
+    def get_video(self, genre: str | None = None) -> dict:
         """
         Picks a random anthem from the list.
 
@@ -25,12 +24,12 @@ class PrideAnthem(commands.Cog):
         """
         if not genre:
             return random.choice(VIDEOS)
-        else:
-            songs = [song for song in VIDEOS if genre.casefold() in song["genre"]]
-            try:
-                return random.choice(songs)
-            except IndexError:
-                log.info("No videos for that genre.")
+
+        songs = [song for song in VIDEOS if genre.casefold() in song["genre"]]
+        try:
+            return random.choice(songs)
+        except IndexError:
+            log.info("No videos for that genre.")
 
     @commands.command(name="prideanthem", aliases=("anthem", "pridesong"))
     async def prideanthem(self, ctx: commands.Context, genre: str = None) -> None:
diff --git a/bot/exts/holidays/pride/pride_facts.py b/bot/exts/holidays/pride/pride_facts.py
index 36a9415e..f3ce50a9 100644
--- a/bot/exts/holidays/pride/pride_facts.py
+++ b/bot/exts/holidays/pride/pride_facts.py
@@ -1,9 +1,8 @@
 import json
 import logging
 import random
-from datetime import datetime
+from datetime import UTC, datetime
 from pathlib import Path
-from typing import Union
 
 import dateutil.parser
 import discord
@@ -29,11 +28,11 @@ class PrideFacts(commands.Cog):
     async def send_pride_fact_daily(self) -> None:
         """Background task to post the daily pride fact every day."""
         channel = self.bot.get_channel(Channels.sir_lancebot_playground)
-        await self.send_select_fact(channel, datetime.utcnow())
+        await self.send_select_fact(channel, datetime.now(tz=UTC))
 
     async def send_random_fact(self, ctx: commands.Context) -> None:
         """Provides a fact from any previous day, or today."""
-        now = datetime.utcnow()
+        now = datetime.now(tz=UTC)
         previous_years_facts = (y for x, y in FACTS.items() if int(x) < now.year)
         current_year_facts = FACTS.get(str(now.year), [])[:now.day]
         previous_facts = current_year_facts + [x for y in previous_years_facts for x in y]
@@ -42,9 +41,9 @@ class PrideFacts(commands.Cog):
         except IndexError:
             await ctx.send("No facts available")
 
-    async def send_select_fact(self, target: discord.abc.Messageable, _date: Union[str, datetime]) -> None:
+    async def send_select_fact(self, target: discord.abc.Messageable, _date: str | datetime) -> None:
         """Provides the fact for the specified day, if the day is today, or is in the past."""
-        now = datetime.utcnow()
+        now = datetime.now(tz=UTC)
         if isinstance(_date, str):
             try:
                 date = dateutil.parser.parse(_date, dayfirst=False, yearfirst=False, fuzzy=True)
@@ -76,7 +75,7 @@ class PrideFacts(commands.Cog):
         will be provided.
         """
         if not option:
-            await self.send_select_fact(ctx, datetime.utcnow())
+            await self.send_select_fact(ctx, datetime.now(tz=UTC))
         elif option.lower().startswith("rand"):
             await self.send_random_fact(ctx)
         else:
diff --git a/bot/exts/holidays/pride/pride_leader.py b/bot/exts/holidays/pride/pride_leader.py
index 120e9e16..b4a98892 100644
--- a/bot/exts/holidays/pride/pride_leader.py
+++ b/bot/exts/holidays/pride/pride_leader.py
@@ -2,7 +2,6 @@ import json
 import logging
 import random
 from pathlib import Path
-from typing import Optional
 
 import discord
 from discord.ext import commands
@@ -90,7 +89,7 @@ class PrideLeader(commands.Cog):
         return embed
 
     @commands.command(aliases=("pl", "prideleader"))
-    async def pride_leader(self, ctx: commands.Context, *, pride_leader_name: Optional[str]) -> None:
+    async def pride_leader(self, ctx: commands.Context, *, pride_leader_name: str | None) -> None:
         """
         Information about a Pride Leader.
 
diff --git a/bot/exts/holidays/valentines/be_my_valentine.py b/bot/exts/holidays/valentines/be_my_valentine.py
index 5ffd14e6..c2dd8bb6 100644
--- a/bot/exts/holidays/valentines/be_my_valentine.py
+++ b/bot/exts/holidays/valentines/be_my_valentine.py
@@ -7,7 +7,7 @@ import discord
 from discord.ext import commands
 
 from bot.bot import Bot
-from bot.constants import Channels, Colours, Lovefest, Month, PYTHON_PREFIX
+from bot.constants import Channels, Colours, Month, PYTHON_PREFIX, Roles
 from bot.utils.decorators import in_month
 from bot.utils.exceptions import MovedCommandError
 
@@ -60,7 +60,7 @@ class BeMyValentine(commands.Cog):
             # This command should only be used in the server
             raise commands.UserInputError("You are supposed to use this command in the server.")
 
-        if Lovefest.role_id not in [role.id for role in user.roles]:
+        if Roles.lovefest not in [role.id for role in user.roles]:
             raise commands.UserInputError(
                 f"You cannot send a valentine to {user} as they do not have the lovefest role!"
             )
@@ -95,7 +95,7 @@ class BeMyValentine(commands.Cog):
         example : .bemyvalentine secret Iceman#6508 Hey I love you, wanna hang around ? (sends the custom message to
         Iceman in DM making you anonymous)
         """
-        if Lovefest.role_id not in [role.id for role in user.roles]:
+        if Roles.lovefest not in [role.id for role in user.roles]:
             await ctx.message.delete()
             raise commands.UserInputError(
                 f"You cannot send a valentine to {user} as they do not have the lovefest role!"
@@ -126,15 +126,14 @@ class BeMyValentine(commands.Cog):
         if valentine_type is None:
             return self.random_valentine()
 
-        elif valentine_type.lower() in ["p", "poem"]:
+        if valentine_type.lower() in ["p", "poem"]:
             return self.valentine_poem(), "A poem dedicated to"
 
-        elif valentine_type.lower() in ["c", "compliment"]:
+        if valentine_type.lower() in ["c", "compliment"]:
             return self.valentine_compliment(), "A compliment for"
 
-        else:
-            # in this case, the user decides to type his own valentine.
-            return valentine_type, "A message for"
+        # in this case, the user decides to type his own valentine.
+        return valentine_type, "A message for"
 
     @staticmethod
     def random_emoji() -> tuple[str, str]:
@@ -148,10 +147,7 @@ class BeMyValentine(commands.Cog):
         valentine_poem = random.choice(self.valentines["valentine_poems"])
         valentine_compliment = random.choice(self.valentines["valentine_compliments"])
         random_valentine = random.choice([valentine_compliment, valentine_poem])
-        if random_valentine == valentine_poem:
-            title = "A poem dedicated to"
-        else:
-            title = "A compliment for "
+        title = "A poem dedicated to" if random_valentine == valentine_poem else "A compliment for "
         return random_valentine, title
 
     def valentine_poem(self) -> str:
diff --git a/bot/exts/holidays/valentines/lovecalculator.py b/bot/exts/holidays/valentines/lovecalculator.py
index c212e833..9b363c5e 100644
--- a/bot/exts/holidays/valentines/lovecalculator.py
+++ b/bot/exts/holidays/valentines/lovecalculator.py
@@ -3,8 +3,8 @@ import hashlib
 import json
 import logging
 import random
+from collections.abc import Coroutine
 from pathlib import Path
-from typing import Coroutine, Optional
 
 import discord
 from discord import Member
@@ -12,7 +12,7 @@ from discord.ext import commands
 from discord.ext.commands import BadArgument, Cog, clean_content
 
 from bot.bot import Bot
-from bot.constants import Channels, Lovefest, Month, PYTHON_PREFIX
+from bot.constants import Channels, Month, PYTHON_PREFIX, Roles
 from bot.utils.decorators import in_month
 
 log = logging.getLogger(__name__)
@@ -27,7 +27,7 @@ class LoveCalculator(Cog):
     @in_month(Month.FEBRUARY)
     @commands.command(aliases=("love_calculator", "love_calc"))
     @commands.cooldown(rate=1, per=5, type=commands.BucketType.user)
-    async def love(self, ctx: commands.Context, who: Member, whom: Optional[Member] = None) -> None:
+    async def love(self, ctx: commands.Context, who: Member, whom: Member | None = None) -> None:
         """
         Tells you how much the two love each other.
 
@@ -45,8 +45,8 @@ class LoveCalculator(Cog):
           Running .love @chrisjl#2655 @joe#6000 will yield the same result as before.
         """
         if (
-            Lovefest.role_id not in [role.id for role in who.roles]
-            or (whom is not None and Lovefest.role_id not in [role.id for role in whom.roles])
+            Roles.lovefest not in [role.id for role in who.roles]
+            or (whom is not None and Roles.lovefest not in [role.id for role in whom.roles])
         ):
             raise BadArgument(
                 "This command can only be ran against members with the lovefest role! "
diff --git a/bot/exts/holidays/valentines/myvalenstate.py b/bot/exts/holidays/valentines/myvalenstate.py
index 8d8772d4..fcef24bc 100644
--- a/bot/exts/holidays/valentines/myvalenstate.py
+++ b/bot/exts/holidays/valentines/myvalenstate.py
@@ -47,7 +47,7 @@ class MyValenstate(commands.Cog):
         else:
             author = name.lower().replace(" ", "")
 
-        for state in STATES.keys():
+        for state in STATES:
             lower_state = state.lower().replace(" ", "")
             eq_chars[state] = self.levenshtein(author, lower_state)
 
@@ -64,8 +64,7 @@ class MyValenstate(commands.Cog):
             embed_text = f"You have another match, this being {matches[0]}."
         else:
             embed_title = "You have a true match!"
-            embed_text = "This state is your true Valenstate! There are no states that would suit" \
-                         " you better"
+            embed_text = "This state is your true Valenstate! There are no states that would suit you better"
 
         embed = discord.Embed(
             title=f"Your Valenstate is {valenstate} \u2764",
diff --git a/bot/exts/holidays/valentines/valentine_zodiac.py b/bot/exts/holidays/valentines/valentine_zodiac.py
index 0a28a5c5..f0c8978d 100644
--- a/bot/exts/holidays/valentines/valentine_zodiac.py
+++ b/bot/exts/holidays/valentines/valentine_zodiac.py
@@ -2,9 +2,8 @@ import calendar
 import json
 import logging
 import random
-from datetime import datetime
+from datetime import UTC, datetime
 from pathlib import Path
-from typing import Union
 
 import discord
 from discord.ext import commands
@@ -78,6 +77,7 @@ class ValentineZodiac(commands.Cog):
             if zodiac_data["start_at"].date() <= query_date.date() <= zodiac_data["end_at"].date():
                 log.trace("Zodiac name sent.")
                 return zodiac_name
+        return None
 
     @commands.group(name="zodiac", invoke_without_command=True)
     async def zodiac(self, ctx: commands.Context, zodiac_sign: str) -> None:
@@ -87,7 +87,7 @@ class ValentineZodiac(commands.Cog):
         log.trace("Embed successfully sent.")
 
     @zodiac.command(name="date")
-    async def date_and_month(self, ctx: commands.Context, date: int, month: Union[int, str]) -> None:
+    async def date_and_month(self, ctx: commands.Context, date: int, month: int | str) -> None:
         """Provides information about zodiac sign by taking month and date as input."""
         if isinstance(month, str):
             month = month.capitalize()
@@ -103,7 +103,7 @@ class ValentineZodiac(commands.Cog):
             final_embed = self.zodiac_build_embed(zodiac)
         else:
             try:
-                zodiac_sign_based_on_date = self.zodiac_date_verifier(datetime(2020, month, date))
+                zodiac_sign_based_on_date = self.zodiac_date_verifier(datetime(2020, month, date, tzinfo=UTC))
                 log.trace("zodiac sign based on month and date received.")
             except ValueError as e:
                 final_embed = discord.Embed()
diff --git a/bot/exts/utilities/bookmark.py b/bot/exts/utilities/bookmark.py
index 0b7ce429..a2d1d1d4 100644
--- a/bot/exts/utilities/bookmark.py
+++ b/bot/exts/utilities/bookmark.py
@@ -1,6 +1,5 @@
 import logging
 import random
-from typing import Optional
 
 import discord
 from discord.ext import commands
@@ -234,15 +233,15 @@ class Bookmark(commands.Cog):
         This command allows deleting any message sent by Sir-Lancebot in the user's DM channel with the bot.
         The command invocation must be a reply to the message that is to be deleted.
         """
-        target_message: Optional[discord.Message] = getattr(ctx.message.reference, "resolved", None)
+        target_message: discord.Message | None = getattr(ctx.message.reference, "resolved", None)
         if target_message is None:
             raise commands.UserInputError("You must reply to the message from Sir-Lancebot you wish to delete.")
 
         if not isinstance(ctx.channel, discord.DMChannel):
             raise commands.UserInputError("You can only run this command your own DMs!")
-        elif target_message.channel != ctx.channel:
+        if target_message.channel != ctx.channel:
             raise commands.UserInputError("You can only delete messages in your own DMs!")
-        elif target_message.author != self.bot.user:
+        if target_message.author != self.bot.user:
             raise commands.UserInputError("You can only delete messages sent by Sir Lancebot!")
 
         await target_message.delete()
diff --git a/bot/exts/utilities/challenges.py b/bot/exts/utilities/challenges.py
index 46bc0fae..2f9ac73e 100644
--- a/bot/exts/utilities/challenges.py
+++ b/bot/exts/utilities/challenges.py
@@ -1,7 +1,6 @@
 import logging
 from asyncio import to_thread
 from random import choice
-from typing import Union
 
 from bs4 import BeautifulSoup
 from discord import Embed, Interaction, SelectOption, ui
@@ -58,7 +57,7 @@ class InformationDropdown(ui.Select):
             SelectOption(
                 label="Other Information",
                 description="See how other people performed on this kata and more!",
-                emoji="ℹ"
+                emoji="🇮"
             )
         ]
 
@@ -101,7 +100,7 @@ class Challenges(commands.Cog):
     def __init__(self, bot: Bot):
         self.bot = bot
 
-    async def kata_id(self, search_link: str, params: dict) -> Union[str, Embed]:
+    async def kata_id(self, search_link: str, params: dict) -> str | Embed:
         """
         Uses bs4 to get the HTML code for the page of katas, where the page is the link of the formatted `search_link`.
 
@@ -123,14 +122,13 @@ class Challenges(commands.Cog):
 
             if not first_kata_div:
                 raise commands.BadArgument("No katas could be found with the filters provided.")
-            else:
-                first_kata_div = choice(first_kata_div)
 
             # There are numerous divs before arriving at the id of the kata, which can be used for the link.
+            first_kata_div = choice(first_kata_div)
             first_kata_id = first_kata_div.a["href"].split("/")[-1]
             return first_kata_id
 
-    async def kata_information(self, kata_id: str) -> Union[dict, Embed]:
+    async def kata_information(self, kata_id: str) -> dict | Embed:
         """
         Returns the information about the Kata.
 
diff --git a/bot/exts/utilities/cheatsheet.py b/bot/exts/utilities/cheatsheet.py
index 3141a050..98ce3f57 100644
--- a/bot/exts/utilities/cheatsheet.py
+++ b/bot/exts/utilities/cheatsheet.py
@@ -1,6 +1,5 @@
 import random
 import re
-from typing import Union
 from urllib.parse import quote_plus
 
 from discord import Embed
@@ -52,7 +51,7 @@ class CheatSheet(commands.Cog):
         )
         return embed
 
-    def result_fmt(self, url: str, body_text: str) -> tuple[bool, Union[str, Embed]]:
+    def result_fmt(self, url: str, body_text: str) -> tuple[bool, str | Embed]:
         """Format Result."""
         if body_text.startswith("#  404 NOT FOUND"):
             embed = self.fmt_error_embed()
@@ -80,7 +79,7 @@ class CheatSheet(commands.Cog):
         aliases=("cht.sh", "cheatsheet", "cheat-sheet", "cht"),
     )
     @commands.cooldown(1, 10, BucketType.user)
-    @whitelist_override(categories=[Categories.help_in_use])
+    @whitelist_override(categories=[Categories.python_help_system])
     async def cheat_sheet(self, ctx: Context, *search_terms: str) -> None:
         """
         Search cheat.sh.
diff --git a/bot/exts/utilities/colour.py b/bot/exts/utilities/colour.py
index 20f97e4b..b8f1d62d 100644
--- a/bot/exts/utilities/colour.py
+++ b/bot/exts/utilities/colour.py
@@ -4,7 +4,6 @@ import pathlib
 import random
 import string
 from io import BytesIO
-from typing import Optional
 
 import discord
 import rapidfuzz
@@ -25,7 +24,7 @@ class Colour(commands.Cog):
         self.bot = bot
         with open(pathlib.Path("bot/resources/utilities/ryanzec_colours.json")) as f:
             self.colour_mapping = json.load(f)
-            del self.colour_mapping['_']  # Delete source credit entry
+            del self.colour_mapping["_"]  # Delete source credit entry
 
     async def send_colour_response(self, ctx: commands.Context, rgb: tuple[int, int, int]) -> None:
         """Create and send embed from user given colour information."""
@@ -84,7 +83,7 @@ class Colour(commands.Cog):
         roles=constants.STAFF_ROLES,
         categories=[constants.Categories.development, constants.Categories.media]
     )
-    async def colour(self, ctx: commands.Context, *, colour_input: Optional[str] = None) -> None:
+    async def colour(self, ctx: commands.Context, *, colour_input: str | None = None) -> None:
         """
         Create an embed that displays colour information.
 
@@ -209,7 +208,7 @@ class Colour(commands.Cog):
     def _rgb_to_hsl(rgb: tuple[int, int, int]) -> tuple[int, int, int]:
         """Convert RGB values to HSL values."""
         rgb_list = [val / 255.0 for val in rgb]
-        h, l, s = colorsys.rgb_to_hls(*rgb_list)
+        h, l, s = colorsys.rgb_to_hls(*rgb_list)  # noqa: E741
         hsl = (round(h * 360), round(s * 100), round(l * 100))
         return hsl
 
@@ -233,7 +232,7 @@ class Colour(commands.Cog):
         hex_code = f"#{hex_}".upper()
         return hex_code
 
-    def _rgb_to_name(self, rgb: tuple[int, int, int]) -> Optional[str]:
+    def _rgb_to_name(self, rgb: tuple[int, int, int]) -> str | None:
         """Convert RGB values to a fuzzy matched name."""
         input_hex_colour = self._rgb_to_hex(rgb)
         try:
@@ -247,7 +246,7 @@ class Colour(commands.Cog):
             colour_name = None
         return colour_name
 
-    def match_colour_name(self, ctx: commands.Context, input_colour_name: str) -> Optional[str]:
+    def match_colour_name(self, ctx: commands.Context, input_colour_name: str) -> str | None:
         """Convert a colour name to HEX code."""
         try:
             match, certainty, _ = rapidfuzz.process.extractOne(
@@ -256,7 +255,7 @@ class Colour(commands.Cog):
                 score_cutoff=80
             )
         except (ValueError, TypeError):
-            return
+            return None
         return f"#{self.colour_mapping[match]}"
 
 
diff --git a/bot/exts/utilities/conversationstarters.py b/bot/exts/utilities/conversationstarters.py
index 410ea884..a019c789 100644
--- a/bot/exts/utilities/conversationstarters.py
+++ b/bot/exts/utilities/conversationstarters.py
@@ -2,7 +2,6 @@ import asyncio
 from contextlib import suppress
 from functools import partial
 from pathlib import Path
-from typing import Union
 
 import discord
 import yaml
@@ -16,11 +15,11 @@ from bot.utils.randomization import RandomCycle
 SUGGESTION_FORM = "https://forms.gle/zw6kkJqv8U43Nfjg9"
 
 with Path("bot/resources/utilities/starter.yaml").open("r", encoding="utf8") as f:
-    STARTERS = yaml.load(f, Loader=yaml.FullLoader)
+    STARTERS = yaml.safe_load(f)
 
 with Path("bot/resources/utilities/py_topics.yaml").open("r", encoding="utf8") as f:
     # First ID is #python-general and the rest are top to bottom categories of Topical Chat/Help.
-    PY_TOPICS = yaml.load(f, Loader=yaml.FullLoader)
+    PY_TOPICS = yaml.safe_load(f)
 
     # Removing `None` from lists of topics, if not a list, it is changed to an empty one.
     PY_TOPICS = {k: [i for i in v if i] if isinstance(v, list) else [] for k, v in PY_TOPICS.items()}
@@ -67,7 +66,7 @@ class ConvoStarters(commands.Cog):
 
     @staticmethod
     def _predicate(
-        command_invoker: Union[discord.User, discord.Member],
+        command_invoker: discord.User | discord.Member,
         message: discord.Message,
         reaction: discord.Reaction,
         user: discord.User
@@ -84,7 +83,7 @@ class ConvoStarters(commands.Cog):
 
     async def _listen_for_refresh(
         self,
-        command_invoker: Union[discord.User, discord.Member],
+        command_invoker: discord.User | discord.Member,
         message: discord.Message
     ) -> None:
         await message.add_reaction("🔄")
diff --git a/bot/exts/utilities/emoji.py b/bot/exts/utilities/emoji.py
index ec40be01..ce352fe2 100644
--- a/bot/exts/utilities/emoji.py
+++ b/bot/exts/utilities/emoji.py
@@ -2,8 +2,7 @@ import logging
 import random
 import textwrap
 from collections import defaultdict
-from datetime import datetime
-from typing import Optional
+from datetime import UTC, datetime
 
 from discord import Color, Embed, Emoji
 from discord.ext import commands
@@ -28,7 +27,7 @@ class Emojis(commands.Cog):
         embed = Embed(
             color=Colours.orange,
             title="Emoji Count",
-            timestamp=datetime.utcnow()
+            timestamp=datetime.now(tz=UTC)
         )
         msg = []
 
@@ -71,7 +70,7 @@ class Emojis(commands.Cog):
         return embed, msg
 
     @commands.group(name="emoji", invoke_without_command=True)
-    async def emoji_group(self, ctx: commands.Context, emoji: Optional[Emoji]) -> None:
+    async def emoji_group(self, ctx: commands.Context, emoji: Emoji | None) -> None:
         """A group of commands related to emojis."""
         if emoji is not None:
             await ctx.invoke(self.info_command, emoji)
diff --git a/bot/exts/utilities/epoch.py b/bot/exts/utilities/epoch.py
index 6f572640..d1ba98bb 100644
--- a/bot/exts/utilities/epoch.py
+++ b/bot/exts/utilities/epoch.py
@@ -1,4 +1,5 @@
-from typing import Optional, Union
+
+import contextlib
 
 import arrow
 import discord
@@ -24,7 +25,7 @@ DROPDOWN_TIMEOUT = 60
 class DateString(commands.Converter):
     """Convert a relative or absolute date/time string to an arrow.Arrow object."""
 
-    async def convert(self, ctx: commands.Context, argument: str) -> Union[arrow.Arrow, Optional[tuple]]:
+    async def convert(self, ctx: commands.Context, argument: str) -> arrow.Arrow | tuple | None:
         """
         Convert a relative or absolute date/time string to an arrow.Arrow object.
 
@@ -88,10 +89,8 @@ class Epoch(commands.Cog):
         view = TimestampMenuView(ctx, self._format_dates(date_time), epoch)
         original = await ctx.send(f"`{epoch}`", view=view)
         await view.wait()  # wait until expiration before removing the dropdown
-        try:
+        with contextlib.suppress(discord.NotFound):
             await original.edit(view=None)
-        except discord.NotFound:  # disregard the error message if the message is deleled
-            pass
 
     @staticmethod
     def _format_dates(date: arrow.Arrow) -> list[str]:
@@ -100,7 +99,7 @@ class Epoch(commands.Cog):
 
         These are used in the description of each style in the dropdown
         """
-        date = date.to('utc')
+        date = date.to("utc")
         formatted = [str(int(date.timestamp()))]
         formatted += [date.format(format[1]) for format in list(STYLES.values())[1:7]]
         formatted.append(date.humanize())
@@ -115,7 +114,7 @@ class TimestampMenuView(discord.ui.View):
         self.ctx = ctx
         self.epoch = epoch
         self.dropdown: discord.ui.Select = self.children[0]
-        for label, date_time in zip(STYLES.keys(), formatted_times):
+        for label, date_time in zip(STYLES.keys(), formatted_times, strict=True):
             self.dropdown.add_option(label=label, description=date_time)
 
     @discord.ui.select(placeholder="Select the format of your timestamp")
diff --git a/bot/exts/utilities/githubinfo.py b/bot/exts/utilities/githubinfo.py
index a7979718..74120f2d 100644
--- a/bot/exts/utilities/githubinfo.py
+++ b/bot/exts/utilities/githubinfo.py
@@ -1,9 +1,8 @@
 import logging
 import random
 import re
-import typing as t
 from dataclasses import dataclass
-from datetime import datetime
+from datetime import UTC, datetime
 from urllib.parse import quote
 
 import discord
@@ -26,7 +25,7 @@ ISSUE_ENDPOINT = "https://api.github.com/repos/{user}/{repository}/issues/{numbe
 PR_ENDPOINT = "https://api.github.com/repos/{user}/{repository}/pulls/{number}"
 
 if Tokens.github:
-    REQUEST_HEADERS["Authorization"] = f"token {Tokens.github}"
+    REQUEST_HEADERS["Authorization"] = f"token {Tokens.github.get_secret_value()}"
 
 CODE_BLOCK_RE = re.compile(
     r"^`([^`\n]+)`"   # Inline codeblock
@@ -48,7 +47,7 @@ AUTOMATIC_REGEX = re.compile(
 class FoundIssue:
     """Dataclass representing an issue found by the regex."""
 
-    organisation: t.Optional[str]
+    organisation: str | None
     repository: str
     number: str
 
@@ -89,7 +88,7 @@ class GithubInfo(commands.Cog):
         number: int,
         repository: str,
         user: str
-    ) -> t.Union[IssueState, FetchError]:
+    ) -> IssueState | FetchError:
         """
         Retrieve an issue from a GitHub repository.
 
@@ -105,9 +104,9 @@ class GithubInfo(commands.Cog):
                 log.info(f"Ratelimit reached while fetching {url}")
                 return FetchError(403, "Ratelimit reached, please retry in a few minutes.")
             return FetchError(403, "Cannot access issue.")
-        elif r.status in (404, 410):
+        if r.status in (404, 410):
             return FetchError(r.status, "Issue not found.")
-        elif r.status != 200:
+        if r.status != 200:
             return FetchError(r.status, "Error while fetching issue.")
 
         # The initial API request is made to the issues API endpoint, which will return information
@@ -141,7 +140,7 @@ class GithubInfo(commands.Cog):
 
     @staticmethod
     def format_embed(
-        results: t.List[t.Union[IssueState, FetchError]]
+        results: list[IssueState | FetchError]
     ) -> discord.Embed:
         """Take a list of IssueState or FetchError and format a Discord embed for them."""
         description_list = []
@@ -261,7 +260,7 @@ class GithubInfo(commands.Cog):
                 description=f"```\n{user_data['bio']}\n```\n" if user_data["bio"] else "",
                 colour=discord.Colour.og_blurple(),
                 url=user_data["html_url"],
-                timestamp=datetime.strptime(user_data["created_at"], "%Y-%m-%dT%H:%M:%SZ")
+                timestamp=datetime.strptime(user_data["created_at"], "%Y-%m-%dT%H:%M:%SZ").replace(tzinfo=UTC)
             )
             embed.set_thumbnail(url=user_data["avatar_url"])
             embed.set_footer(text="Account created at")
@@ -293,7 +292,7 @@ class GithubInfo(commands.Cog):
 
         await ctx.send(embed=embed)
 
-    @github_group.command(name='repository', aliases=('repo',))
+    @github_group.command(name="repository", aliases=("repo",))
     async def github_repo_info(self, ctx: commands.Context, *repo: str) -> None:
         """
         Fetches a repositories' GitHub information.
@@ -347,8 +346,12 @@ class GithubInfo(commands.Cog):
             icon_url=repo_owner["avatar_url"]
         )
 
-        repo_created_at = datetime.strptime(repo_data["created_at"], "%Y-%m-%dT%H:%M:%SZ").strftime("%d/%m/%Y")
-        last_pushed = datetime.strptime(repo_data["pushed_at"], "%Y-%m-%dT%H:%M:%SZ").strftime("%d/%m/%Y at %H:%M")
+        repo_created_at = datetime.strptime(
+            repo_data["created_at"], "%Y-%m-%dT%H:%M:%SZ"
+        ).replace(tzinfo=UTC).strftime("%d/%m/%Y")
+        last_pushed = datetime.strptime(
+            repo_data["pushed_at"], "%Y-%m-%dT%H:%M:%SZ"
+        ).replace(tzinfo=UTC).strftime("%d/%m/%Y at %H:%M")
 
         embed.set_footer(
             text=(
diff --git a/bot/exts/utilities/realpython.py b/bot/exts/utilities/realpython.py
index 46b02866..c63fca85 100644
--- a/bot/exts/utilities/realpython.py
+++ b/bot/exts/utilities/realpython.py
@@ -1,6 +1,5 @@
 import logging
 from html import unescape
-from typing import Optional
 from urllib.parse import quote_plus
 
 from discord import Embed
@@ -31,8 +30,13 @@ class RealPython(commands.Cog):
 
     @commands.command(aliases=["rp"])
     @commands.cooldown(1, 10, commands.cooldowns.BucketType.user)
-    async def realpython(self, ctx: commands.Context, amount: Optional[int] = 5, *,
-                         user_search: Optional[str] = None) -> None:
+    async def realpython(
+        self,
+        ctx: commands.Context,
+        amount: int | None = 5,
+        *,
+        user_search: str | None = None
+    ) -> None:
         """
         Send some articles from RealPython that match the search terms.
 
diff --git a/bot/exts/utilities/reddit.py b/bot/exts/utilities/reddit.py
index 028c16bc..f8e358de 100644
--- a/bot/exts/utilities/reddit.py
+++ b/bot/exts/utilities/reddit.py
@@ -3,8 +3,7 @@ import logging
 import random
 import textwrap
 from collections import namedtuple
-from datetime import datetime, timedelta
-from typing import Union
+from datetime import UTC, datetime, timedelta
 
 from aiohttp import BasicAuth, ClientError
 from discord import Colour, Embed, TextChannel
@@ -36,15 +35,15 @@ class Reddit(Cog):
 
         self.webhook = None
         self.access_token = None
-        self.client_auth = BasicAuth(RedditConfig.client_id, RedditConfig.secret)
+        self.client_auth = BasicAuth(RedditConfig.client_id.get_secret_value(), RedditConfig.secret.get_secret_value())
 
         self.auto_poster_loop.start()
 
     async def cog_unload(self) -> None:
         """Stop the loop task and revoke the access token when the cog is unloaded."""
         self.auto_poster_loop.cancel()
-        if self.access_token and self.access_token.expires_at > datetime.utcnow():
-            asyncio.create_task(self.revoke_access_token())
+        if self.access_token and self.access_token.expires_at > datetime.now(tz=UTC):
+            await self.revoke_access_token()
 
     async def cog_load(self) -> None:
         """Sets the reddit webhook when the cog is loaded."""
@@ -55,7 +54,7 @@ class Reddit(Cog):
         """Get the #reddit channel object from the bot's cache."""
         return self.bot.get_channel(Channels.reddit)
 
-    def build_pagination_pages(self, posts: list[dict], paginate: bool) -> Union[list[tuple], str]:
+    def build_pagination_pages(self, posts: list[dict], paginate: bool) -> list[tuple] | str:
         """Build embed pages required for Paginator."""
         pages = []
         first_page = ""
@@ -138,17 +137,15 @@ class Reddit(Cog):
                 expiration = int(content["expires_in"]) - 60  # Subtract 1 minute for leeway.
                 self.access_token = AccessToken(
                     token=content["access_token"],
-                    expires_at=datetime.utcnow() + timedelta(seconds=expiration)
+                    expires_at=datetime.now(tz=UTC) + timedelta(seconds=expiration)
                 )
 
                 log.debug(f"New token acquired; expires on UTC {self.access_token.expires_at}")
                 return
-            else:
-                log.debug(
-                    f"Failed to get an access token: "
-                    f"status {response.status} & content type {response.content_type}; "
-                    f"retrying ({i}/{self.MAX_RETRIES})"
-                )
+            log.debug(
+                f"Failed to get an access token: status {response.status} & content type {response.content_type}; "
+                f"retrying ({i}/{self.MAX_RETRIES})"
+            )
 
             await asyncio.sleep(3)
 
@@ -183,7 +180,7 @@ class Reddit(Cog):
             raise ValueError("Invalid amount of subreddit posts requested.")
 
         # Renew the token if necessary.
-        if not self.access_token or self.access_token.expires_at < datetime.utcnow():
+        if not self.access_token or self.access_token.expires_at < datetime.now(tz=UTC):
             await self.get_access_token()
 
         url = f"{self.OAUTH_URL}/{route}"
@@ -193,7 +190,7 @@ class Reddit(Cog):
                 headers={**self.HEADERS, "Authorization": f"bearer {self.access_token.token}"},
                 params=params
             )
-            if response.status == 200 and response.content_type == 'application/json':
+            if response.status == 200 and response.content_type == "application/json":
                 # Got appropriate response - process and return.
                 content = await response.json()
                 posts = content["data"]["children"]
@@ -205,11 +202,11 @@ class Reddit(Cog):
             await asyncio.sleep(3)
 
         log.debug(f"Invalid response from: {url} - status code {response.status}, mimetype {response.content_type}")
-        return list()  # Failed to get appropriate response within allowed number of retries.
+        return []  # Failed to get appropriate response within allowed number of retries.
 
     async def get_top_posts(
             self, subreddit: Subreddit, time: str = "all", amount: int = 5, paginate: bool = False
-    ) -> Union[Embed, list[tuple]]:
+    ) -> Embed | list[tuple]:
         """
         Get the top amount of posts for a given subreddit within a specified timeframe.
 
@@ -248,7 +245,7 @@ class Reddit(Cog):
         """Post the top 5 posts daily, and the top 5 posts weekly."""
         # once d.py get support for `time` parameter in loop decorator,
         # this can be removed and the loop can use the `time=datetime.time.min` parameter
-        now = datetime.utcnow()
+        now = datetime.now(tz=UTC)
         tomorrow = now + timedelta(days=1)
         midnight_tomorrow = tomorrow.replace(hour=0, minute=0, second=0)
 
@@ -257,7 +254,7 @@ class Reddit(Cog):
         if not self.webhook:
             await self.bot.fetch_webhook(RedditConfig.webhook)
 
-        if datetime.utcnow().weekday() == 0:
+        if datetime.now(tz=UTC).weekday() == 0:
             await self.top_weekly_posts()
             # if it's a monday send the top weekly posts
 
@@ -358,6 +355,6 @@ class Reddit(Cog):
 async def setup(bot: Bot) -> None:
     """Load the Reddit cog."""
     if not RedditConfig.secret or not RedditConfig.client_id:
-        log.error("Credentials not provided, cog not loaded.")
+        log.warning("Credentials not provided, cog not loaded.")
         return
     await bot.add_cog(Reddit(bot))
diff --git a/bot/exts/utilities/stackoverflow.py b/bot/exts/utilities/stackoverflow.py
index b248e83f..1eeff45b 100644
--- a/bot/exts/utilities/stackoverflow.py
+++ b/bot/exts/utilities/stackoverflow.py
@@ -42,10 +42,10 @@ class Stackoverflow(commands.Cog):
             if response.status == 200:
                 data = await response.json()
             else:
-                logger.error(f'Status code is not 200, it is {response.status}')
+                logger.error(f"Status code is not 200, it is {response.status}")
                 await ctx.send(embed=ERR_EMBED)
                 return
-        if not data['items']:
+        if not data["items"]:
             no_search_result = Embed(
                 title=f"No search results found for {search_query}",
                 color=Colours.soft_red
@@ -63,7 +63,7 @@ class Stackoverflow(commands.Cog):
         )
         for item in top5:
             embed.add_field(
-                name=unescape(item['title']),
+                name=unescape(item["title"]),
                 value=(
                     f"[{Emojis.reddit_upvote} {item['score']}    "
                     f"{Emojis.stackoverflow_views} {item['view_count']}     "
diff --git a/bot/exts/utilities/twemoji.py b/bot/exts/utilities/twemoji.py
index 25a03d25..a936f733 100644
--- a/bot/exts/utilities/twemoji.py
+++ b/bot/exts/utilities/twemoji.py
@@ -1,6 +1,6 @@
 import logging
 import re
-from typing import Literal, Optional
+from typing import Literal
 
 import discord
 from discord.ext import commands
@@ -57,7 +57,7 @@ class Twemoji(commands.Cog):
         return embed
 
     @staticmethod
-    def emoji(codepoint: Optional[str]) -> Optional[str]:
+    def emoji(codepoint: str | None) -> str | None:
         """
         Returns the emoji corresponding to a given `codepoint`, or `None` if no emoji was found.
 
@@ -66,9 +66,10 @@ class Twemoji(commands.Cog):
         """
         if code := Twemoji.trim_code(codepoint):
             return chr(int(code, 16))
+        return None
 
     @staticmethod
-    def codepoint(emoji: Optional[str]) -> Optional[str]:
+    def codepoint(emoji: str | None) -> str | None:
         """
         Returns the codepoint, in a trimmed format, of a single emoji.
 
@@ -82,7 +83,7 @@ class Twemoji(commands.Cog):
         return hex(ord(emoji)).removeprefix("0x")
 
     @staticmethod
-    def trim_code(codepoint: Optional[str]) -> Optional[str]:
+    def trim_code(codepoint: str | None) -> str | None:
         """
         Returns the meaningful information from the given `codepoint`.
 
@@ -98,6 +99,7 @@ class Twemoji(commands.Cog):
         """
         if code := CODEPOINT_REGEX.search(codepoint or ""):
             return code.group()
+        return None
 
     @staticmethod
     def codepoint_from_input(raw_emoji: tuple[str, ...]) -> str:
diff --git a/bot/exts/utilities/wikipedia.py b/bot/exts/utilities/wikipedia.py
index d87982c9..d12cb19d 100644
--- a/bot/exts/utilities/wikipedia.py
+++ b/bot/exts/utilities/wikipedia.py
@@ -1,6 +1,6 @@
 import logging
 import re
-from datetime import datetime
+from datetime import UTC, datetime
 from html import unescape
 
 from discord import Color, Embed, TextChannel
@@ -85,7 +85,7 @@ class WikipediaSearch(commands.Cog):
                 colour=Color.og_blurple()
             )
             embed.set_thumbnail(url=WIKI_THUMBNAIL)
-            embed.timestamp = datetime.utcnow()
+            embed.timestamp = datetime.now(tz=UTC)
             await LinePaginator.paginate(contents, ctx, embed, restrict_to_user=ctx.author)
         else:
             await ctx.send(
diff --git a/bot/exts/utilities/wolfram.py b/bot/exts/utilities/wolfram.py
index a2f1228a..d5669c6b 100644
--- a/bot/exts/utilities/wolfram.py
+++ b/bot/exts/utilities/wolfram.py
@@ -1,6 +1,6 @@
 import logging
+from collections.abc import Callable
 from io import BytesIO
-from typing import Callable, Optional
 from urllib.parse import urlencode
 
 import arrow
@@ -10,12 +10,12 @@ from discord.ext import commands
 from discord.ext.commands import BucketType, Cog, Context, check, group
 
 from bot.bot import Bot
-from bot.constants import Colours, STAFF_ROLES, Wolfram
+from bot.constants import Colours, STAFF_ROLES, Wolfram as WolframConfig
 from bot.utils.pagination import ImagePaginator
 
 log = logging.getLogger(__name__)
 
-APPID = Wolfram.key
+APPID = WolframConfig.key.get_secret_value()
 DEFAULT_OUTPUT_FORMAT = "JSON"
 QUERY = "http://api.wolframalpha.com/v2/{request}"
 WOLF_IMAGE = "https://www.symbols.com/gi.php?type=1&id=2886&i=1"
@@ -23,10 +23,10 @@ WOLF_IMAGE = "https://www.symbols.com/gi.php?type=1&id=2886&i=1"
 MAX_PODS = 20
 
 # Allows for 10 wolfram calls pr user pr day
-usercd = commands.CooldownMapping.from_cooldown(Wolfram.user_limit_day, 60 * 60 * 24, BucketType.user)
+usercd = commands.CooldownMapping.from_cooldown(WolframConfig.user_limit_day, 60 * 60 * 24, BucketType.user)
 
 # Allows for max api requests / days in month per day for the entire guild (Temporary)
-guildcd = commands.CooldownMapping.from_cooldown(Wolfram.guild_limit_day, 60 * 60 * 24, BucketType.guild)
+guildcd = commands.CooldownMapping.from_cooldown(WolframConfig.guild_limit_day, 60 * 60 * 24, BucketType.guild)
 
 
 async def send_embed(
@@ -64,10 +64,10 @@ def custom_cooldown(*ignore: int) -> Callable:
         if ctx.invoked_with == "help":
             # if the invoked command is help we don't want to increase the ratelimits since it's not actually
             # invoking the command/making a request, so instead just check if the user/guild are on cooldown.
-            guild_cooldown = not guildcd.get_bucket(ctx.message).get_tokens() == 0  # if guild is on cooldown
+            guild_cooldown = guildcd.get_bucket(ctx.message).get_tokens() != 0  # if guild is on cooldown
             # check the message is in a guild, and check user bucket if user is not ignored
             if ctx.guild and not any(r.id in ignore for r in ctx.author.roles):
-                return guild_cooldown and not usercd.get_bucket(ctx.message).get_tokens() == 0
+                return guild_cooldown and usercd.get_bucket(ctx.message).get_tokens() != 0
             return guild_cooldown
 
         user_bucket = usercd.get_bucket(ctx.message)
@@ -105,7 +105,7 @@ def custom_cooldown(*ignore: int) -> Callable:
     return check(predicate)
 
 
-async def get_pod_pages(ctx: Context, bot: Bot, query: str) -> Optional[list[tuple[str, str]]]:
+async def get_pod_pages(ctx: Context, bot: Bot, query: str) -> list[tuple[str, str]] | None:
     """Get the Wolfram API pod pages for the provided query."""
     async with ctx.typing():
         params = {
@@ -253,10 +253,7 @@ class Wolfram(Cog):
         if not pages:
             return
 
-        if len(pages) >= 2:
-            page = pages[1]
-        else:
-            page = pages[0]
+        page = pages[1] if len(pages) >= 2 else pages[0]
 
         await send_embed(ctx, page[0], colour=Colours.soft_orange, img_url=page[1])
 
@@ -303,4 +300,7 @@ class Wolfram(Cog):
 
 async def setup(bot: Bot) -> None:
     """Load the Wolfram cog."""
+    if not WolframConfig.key:
+        log.warning("No Wolfram API Key was provided. Not loading Wolfram Cog.")
+        return
     await bot.add_cog(Wolfram(bot))
diff --git a/bot/exts/utilities/wtf_python.py b/bot/exts/utilities/wtf_python.py
index 0c0375cb..29a9611c 100644
--- a/bot/exts/utilities/wtf_python.py
+++ b/bot/exts/utilities/wtf_python.py
@@ -1,7 +1,6 @@
 import logging
 import random
 import re
-from typing import Optional
 
 import rapidfuzz
 from discord import Embed, File
@@ -67,7 +66,7 @@ class WTFPython(commands.Cog):
                 hyper_link = match[0].split("(")[1].replace(")", "")
                 self.headers[match[0]] = f"{BASE_URL}/{hyper_link}"
 
-    def fuzzy_match_header(self, query: str) -> Optional[str]:
+    def fuzzy_match_header(self, query: str) -> str | None:
         """
         Returns the fuzzy match of a query if its ratio is above "MINIMUM_CERTAINTY" else returns None.
 
@@ -79,7 +78,7 @@ class WTFPython(commands.Cog):
         return match if certainty > MINIMUM_CERTAINTY else None
 
     @commands.command(aliases=("wtf",))
-    async def wtf_python(self, ctx: commands.Context, *, query: Optional[str] = None) -> None:
+    async def wtf_python(self, ctx: commands.Context, *, query: str | None = None) -> None:
         """
         Search WTF Python repository.
 
diff --git a/bot/utils/__init__.py b/bot/utils/__init__.py
index 91682dbc..ddc2d111 100644
--- a/bot/utils/__init__.py
+++ b/bot/utils/__init__.py
@@ -3,8 +3,7 @@ import contextlib
 import re
 import string
 from collections.abc import Iterable
-from datetime import datetime
-from typing import Optional
+from datetime import UTC, datetime
 
 import discord
 from discord.ext.commands import BadArgument, Context
@@ -27,8 +26,7 @@ def resolve_current_month() -> Month:
     """
     if Client.month_override is not None:
         return Month(Client.month_override)
-    else:
-        return Month(datetime.utcnow().month)
+    return Month(datetime.now(tz=UTC).month)
 
 
 async def disambiguate(
@@ -38,7 +36,7 @@ async def disambiguate(
     timeout: float = 30,
     entries_per_page: int = 20,
     empty: bool = False,
-    embed: Optional[discord.Embed] = None
+    embed: discord.Embed | None = None
 ) -> str:
     """
     Has the user choose between multiple entries in case one could not be chosen automatically.
@@ -130,9 +128,9 @@ def replace_many(
         assert var == "That WAS a sentence"
     """
     if ignore_case:
-        replacements = dict(
-            (word.lower(), replacement) for word, replacement in replacements.items()
-        )
+        replacements = {
+            word.lower(): replacement for word, replacement in replacements.items()
+        }
 
     words_to_replace = sorted(replacements, key=lambda s: (-len(s), s))
 
@@ -152,10 +150,9 @@ def replace_many(
         cleaned_word = word.translate(str.maketrans("", "", string.punctuation))
         if cleaned_word.isupper():
             return replacement.upper()
-        elif cleaned_word[0].isupper():
+        if cleaned_word[0].isupper():
             return replacement.capitalize()
-        else:
-            return replacement.lower()
+        return replacement.lower()
 
     return regex.sub(_repl, sentence)
 
diff --git a/bot/utils/checks.py b/bot/utils/checks.py
index 857b6746..f1c2b3ce 100644
--- a/bot/utils/checks.py
+++ b/bot/utils/checks.py
@@ -1,7 +1,6 @@
 import datetime
 import logging
-from collections.abc import Container, Iterable
-from typing import Callable, Optional
+from collections.abc import Callable, Container, Iterable
 
 from discord.ext.commands import (
     BucketType, CheckFailure, Cog, Command, CommandOnCooldown, Context, Cooldown, CooldownMapping
@@ -10,12 +9,13 @@ from discord.ext.commands import (
 from bot import constants
 
 log = logging.getLogger(__name__)
+CODEJAM_CATEGORY_NAME = "Code Jam"
 
 
 class InWhitelistCheckFailure(CheckFailure):
     """Raised when the `in_whitelist` check fails."""
 
-    def __init__(self, redirect_channel: Optional[int]):
+    def __init__(self, redirect_channel: int | None):
         self.redirect_channel = redirect_channel
 
         if redirect_channel:
@@ -33,7 +33,7 @@ def in_whitelist_check(
     channels: Container[int] = (),
     categories: Container[int] = (),
     roles: Container[int] = (),
-    redirect: Optional[int] = constants.Channels.sir_lancebot_playground,
+    redirect: int | None = constants.Channels.sir_lancebot_playground,
     fail_silently: bool = False,
 ) -> bool:
     """
@@ -74,7 +74,7 @@ def in_whitelist_check(
         return True
 
     category = getattr(ctx_channel, "category", None)
-    if category and category.name == constants.codejam_categories_name:
+    if category and category.name == CODEJAM_CATEGORY_NAME:
         log.trace(f"{ctx.author} may use the `{ctx.command.name}` command as they are in a codejam team channel.")
         return True
 
@@ -153,7 +153,7 @@ def cooldown_with_role_bypass(rate: int, per: float, type: BucketType = BucketTy
             return
 
         # Cooldown logic, taken from discord.py internals.
-        current = ctx.message.created_at.replace(tzinfo=datetime.timezone.utc).timestamp()
+        current = ctx.message.created_at.replace(tzinfo=datetime.UTC).timestamp()
         bucket = buckets.get_bucket(ctx.message)
         retry_after = bucket.update_rate_limit(current)
         if retry_after:
diff --git a/bot/utils/converters.py b/bot/utils/converters.py
index 7227a406..6111b87d 100644
--- a/bot/utils/converters.py
+++ b/bot/utils/converters.py
@@ -1,5 +1,4 @@
-from datetime import datetime
-from typing import Union
+from datetime import UTC, datetime
 
 import discord
 from discord.ext import commands
@@ -47,7 +46,7 @@ class CoordinateConverter(commands.Converter):
         return x, y
 
 
-SourceType = Union[commands.Command, commands.Cog]
+SourceType = commands.Command | commands.Cog
 
 
 class SourceConverter(commands.Converter):
@@ -73,12 +72,12 @@ class DateConverter(commands.Converter):
     """Parse SOL or earth date (in format YYYY-MM-DD) into `int` or `datetime`. When invalid input, raise error."""
 
     @staticmethod
-    async def convert(ctx: commands.Context, argument: str) -> Union[int, datetime]:
+    async def convert(ctx: commands.Context, argument: str) -> int | datetime:
         """Parse date (SOL or earth) into `datetime` or `int`. When invalid value, raise error."""
         if argument.isdecimal():
             return int(argument)
         try:
-            date = datetime.strptime(argument, "%Y-%m-%d")
+            date = datetime.strptime(argument, "%Y-%m-%d").replace(tzinfo=UTC)
         except ValueError:
             raise commands.BadArgument(
                 f"Can't convert `{argument}` to `datetime` in format `YYYY-MM-DD` or `int` in SOL."
diff --git a/bot/utils/decorators.py b/bot/utils/decorators.py
index 442eb841..1cbad504 100644
--- a/bot/utils/decorators.py
+++ b/bot/utils/decorators.py
@@ -3,9 +3,8 @@ import functools
 import logging
 import random
 from asyncio import Lock
-from collections.abc import Container
+from collections.abc import Callable, Container
 from functools import wraps
-from typing import Callable, Optional, Union
 from weakref import WeakValueDictionary
 
 from discord import Colour, Embed
@@ -24,16 +23,12 @@ log = logging.getLogger(__name__)
 class InChannelCheckFailure(CheckFailure):
     """Check failure when the user runs a command in a non-whitelisted channel."""
 
-    pass
-
 
 class InMonthCheckFailure(CheckFailure):
     """Check failure for when a command is invoked outside of its allowed month."""
 
-    pass
-
 
-def seasonal_task(*allowed_months: Month, sleep_time: Union[float, int] = ONE_DAY) -> Callable:
+def seasonal_task(*allowed_months: Month, sleep_time: float | int = ONE_DAY) -> Callable:
     """
     Perform the decorated method periodically in `allowed_months`.
 
@@ -79,8 +74,8 @@ def in_month_listener(*allowed_months: Month) -> Callable:
             if current_month in allowed_months:
                 # Propagate return value although it should always be None
                 return await listener(*args, **kwargs)
-            else:
-                log.debug(f"Guarded {listener.__qualname__} from invoking in {current_month!s}")
+            log.debug(f"Guarded {listener.__qualname__} from invoking in {current_month!s}")
+            return None
         return guarded_listener
     return decorator
 
@@ -101,8 +96,7 @@ def in_month_command(*allowed_months: Month) -> Callable:
         )
         if can_run:
             return True
-        else:
-            raise InMonthCheckFailure(f"Command can only be used in {human_months(allowed_months)}")
+        raise InMonthCheckFailure(f"Command can only be used in {human_months(allowed_months)}")
 
     return commands.check(predicate)
 
@@ -201,13 +195,13 @@ def whitelist_check(**default_kwargs: Container[int]) -> Callable[[Context], boo
 
         # Determine which command's overrides we will use. Group commands will
         # inherit from their parents if they don't define their own overrides
-        overridden_command: Optional[commands.Command] = None
+        overridden_command: commands.Command | None = None
         for command in [ctx.command, *ctx.command.parents]:
             if hasattr(command.callback, "override"):
                 overridden_command = command
                 break
         if overridden_command is not None:
-            log.debug(f'Command {overridden_command} has overrides')
+            log.debug(f"Command {overridden_command} has overrides")
             if overridden_command is not ctx.command:
                 log.debug(
                     f"Command '{ctx.command.qualified_name}' inherited overrides "
@@ -319,7 +313,7 @@ def whitelist_override(bypass_defaults: bool = False, allow_dm: bool = False, **
     return inner
 
 
-def locked() -> Optional[Callable]:
+def locked() -> Callable | None:
     """
     Allows the user to only run one instance of the decorated command at a time.
 
@@ -327,11 +321,11 @@ def locked() -> Optional[Callable]:
 
     This decorator has to go before (below) the `command` decorator.
     """
-    def wrap(func: Callable) -> Optional[Callable]:
+    def wrap(func: Callable) -> Callable | None:
         func.__locks = WeakValueDictionary()
 
         @wraps(func)
-        async def inner(self: Callable, ctx: Context, *args, **kwargs) -> Optional[Callable]:
+        async def inner(self: Callable, ctx: Context, *args, **kwargs) -> Callable | None:
             lock = func.__locks.setdefault(ctx.author.id, Lock())
             if lock.locked():
                 embed = Embed()
@@ -344,7 +338,7 @@ def locked() -> Optional[Callable]:
                 )
                 embed.title = random.choice(ERROR_REPLIES)
                 await ctx.send(embed=embed)
-                return
+                return None
 
             async with func.__locks.setdefault(ctx.author.id, Lock()):
                 return await func(self, ctx, *args, **kwargs)
diff --git a/bot/utils/exceptions.py b/bot/utils/exceptions.py
index 3cd96325..b1a35e63 100644
--- a/bot/utils/exceptions.py
+++ b/bot/utils/exceptions.py
@@ -1,16 +1,13 @@
-from typing import Optional
 
 
 class UserNotPlayingError(Exception):
     """Raised when users try to use game commands when they are not playing."""
 
-    pass
-
 
 class APIError(Exception):
     """Raised when an external API (eg. Wikipedia) returns an error response."""
 
-    def __init__(self, api: str, status_code: int, error_msg: Optional[str] = None):
+    def __init__(self, api: str, status_code: int, error_msg: str | None = None):
         super().__init__()
         self.api = api
         self.status_code = status_code
diff --git a/bot/utils/messages.py b/bot/utils/messages.py
index b0c95583..4fb0b39b 100644
--- a/bot/utils/messages.py
+++ b/bot/utils/messages.py
@@ -1,6 +1,7 @@
+import contextlib
 import logging
 import re
-from typing import Callable, Optional, Union
+from collections.abc import Callable
 
 from discord import Embed, Message
 from discord.ext import commands
@@ -9,39 +10,35 @@ from discord.ext.commands import Context, MessageConverter
 log = logging.getLogger(__name__)
 
 
-def sub_clyde(username: Optional[str]) -> Optional[str]:
+def sub_clyde(username: str | None) -> str | None:
     """
-    Replace "e"/"E" in any "clyde" in `username` with a Cyrillic "е"/"E" and return the new string.
+    Replace "e"/"E" in any "clyde" in `username` with a Cyrillic "е"/"Е" and return the new string.
 
     Discord disallows "clyde" anywhere in the username for webhooks. It will return a 400.
     Return None only if `username` is None.
-    """
+    """  # noqa: RUF002
     def replace_e(match: re.Match) -> str:
-        char = "е" if match[2] == "e" else "Е"
+        char = "е" if match[2] == "e" else "Е"  # noqa: RUF001
         return match[1] + char
 
     if username:
         return re.sub(r"(clyd)(e)", replace_e, username, flags=re.I)
-    else:
-        return username  # Empty string or None
+    return username  # Empty string or None
 
 
-async def get_discord_message(ctx: Context, text: str) -> Union[Message, str]:
+async def get_discord_message(ctx: Context, text: str) -> Message | str:
     """
     Attempts to convert a given `text` to a discord Message object and return it.
 
     Conversion will succeed if given a discord Message ID or link.
     Returns `text` if the conversion fails.
     """
-    try:
+    with contextlib.suppress(commands.BadArgument):
         text = await MessageConverter().convert(ctx, text)
-    except commands.BadArgument:
-        pass
-
     return text
 
 
-async def get_text_and_embed(ctx: Context, text: str) -> tuple[str, Optional[Embed]]:
+async def get_text_and_embed(ctx: Context, text: str) -> tuple[str, Embed | None]:
     """
     Attempts to extract the text and embed from a possible link to a discord Message.
 
@@ -52,7 +49,7 @@ async def get_text_and_embed(ctx: Context, text: str) -> tuple[str, Optional[Emb
         str: If `text` is a valid discord Message, the contents of the message, else `text`.
         Optional[Embed]: The embed if found in the valid Message, else None
     """
-    embed: Optional[Embed] = None
+    embed: Embed | None = None
 
     msg = await get_discord_message(ctx, text)
     # Ensure the user has read permissions for the channel the message is in
diff --git a/bot/utils/pagination.py b/bot/utils/pagination.py
index b291f7db..ef3186d0 100644
--- a/bot/utils/pagination.py
+++ b/bot/utils/pagination.py
@@ -1,7 +1,6 @@
 import asyncio
 import logging
 from collections.abc import Iterable
-from typing import Optional
 
 from discord import Embed, Member, Reaction
 from discord.abc import User
@@ -29,10 +28,10 @@ class LinePaginator(Paginator):
 
     def __init__(
             self,
-            prefix: str = '```',
-            suffix: str = '```',
+            prefix: str = "```",
+            suffix: str = "```",
             max_size: int = 2000,
-            max_lines: Optional[int] = None,
+            max_lines: int | None = None,
             linesep: str = "\n"
     ):
         """
@@ -87,11 +86,13 @@ class LinePaginator(Paginator):
             self._count += 1
 
     @classmethod
-    async def paginate(cls, lines: Iterable[str], ctx: Context, embed: Embed,
-                       prefix: str = "", suffix: str = "", max_lines: Optional[int] = None,
-                       max_size: int = 500, empty: bool = True, restrict_to_user: User = None,
-                       timeout: int = 300, footer_text: str = None, url: str = None,
-                       exception_on_empty_embed: bool = False) -> None:
+    async def paginate(
+        cls, lines: Iterable[str], ctx: Context,
+        embed: Embed, prefix: str = "", suffix: str = "",
+        max_lines: int | None = None, max_size: int = 500, empty: bool = True,
+        restrict_to_user: User = None, timeout: int = 300, footer_text: str = None,
+        url: str = None, exception_on_empty_embed: bool = False
+    ) -> None:
         """
         Use a paginator and set of reactions to provide pagination over a set of lines.
 
@@ -170,26 +171,26 @@ class LinePaginator(Paginator):
 
             log.debug("There's less than two pages, so we won't paginate - sending single page on its own")
             await ctx.send(embed=embed)
-            return
+            return None
+
+        if footer_text:
+            embed.set_footer(text=f"{footer_text} (Page {current_page + 1}/{len(paginator.pages)})")
         else:
-            if footer_text:
-                embed.set_footer(text=f"{footer_text} (Page {current_page + 1}/{len(paginator.pages)})")
-            else:
-                embed.set_footer(text=f"Page {current_page + 1}/{len(paginator.pages)}")
-            log.trace(f"Setting embed footer to '{embed.footer.text}'")
+            embed.set_footer(text=f"Page {current_page + 1}/{len(paginator.pages)}")
+        log.trace(f"Setting embed footer to '{embed.footer.text}'")
 
-            if url:
-                embed.url = url
-                log.trace(f"Setting embed url to '{url}'")
+        if url:
+            embed.url = url
+            log.trace(f"Setting embed url to '{url}'")
 
-            log.debug("Sending first page to channel...")
-            message = await ctx.send(embed=embed)
+        log.debug("Sending first page to channel...")
+        message = await ctx.send(embed=embed)
 
         log.debug("Adding emoji reactions to message...")
 
         for emoji in PAGINATION_EMOJI:
             # Add all the applicable emoji to the message
-            log.trace(f"Adding reaction: {repr(emoji)}")
+            log.trace(f"Adding reaction: {emoji!r}")
             await message.add_reaction(emoji)
 
         while True:
@@ -270,6 +271,7 @@ class LinePaginator(Paginator):
 
         log.debug("Ending pagination and clearing reactions...")
         await message.clear_reactions()
+        return None
 
 
 class ImagePaginator(Paginator):
@@ -358,7 +360,7 @@ class ImagePaginator(Paginator):
 
         if len(paginator.pages) <= 1:
             await ctx.send(embed=embed)
-            return
+            return None
 
         embed.set_footer(text=f"Page {current_page + 1}/{len(paginator.pages)}")
         message = await ctx.send(embed=embed)
@@ -431,3 +433,4 @@ class ImagePaginator(Paginator):
 
         log.debug("Ending pagination and clearing reactions...")
         await message.clear_reactions()
+        return None
diff --git a/bot/utils/randomization.py b/bot/utils/randomization.py
index c9eabbd2..1caff3fa 100644
--- a/bot/utils/randomization.py
+++ b/bot/utils/randomization.py
@@ -1,7 +1,9 @@
 import itertools
 import random
 from collections.abc import Iterable
-from typing import Any
+from typing import TypeVar
+
+T = TypeVar("T")
 
 
 class RandomCycle:
@@ -11,11 +13,11 @@ class RandomCycle:
     The iterable is reshuffled after each full cycle.
     """
 
-    def __init__(self, iterable: Iterable):
+    def __init__(self, iterable: Iterable[T]):
         self.iterable = list(iterable)
         self.index = itertools.cycle(range(len(iterable)))
 
-    def __next__(self) -> Any:
+    def __next__(self) -> T:
         idx = next(self.index)
 
         if idx == 0:
diff --git a/bot/utils/time.py b/bot/utils/time.py
index fbf2fd21..66f9e7cb 100644
--- a/bot/utils/time.py
+++ b/bot/utils/time.py
@@ -1,4 +1,4 @@
-import datetime
+from datetime import UTC, datetime
 
 from dateutil.relativedelta import relativedelta
 
@@ -17,12 +17,11 @@ def _stringify_time_unit(value: int, unit: str) -> str:
     """
     if unit == "seconds" and value == 0:
         return "0 seconds"
-    elif value == 1:
+    if value == 1:
         return f"{value} {unit[:-1]}"
-    elif value == 0:
+    if value == 0:
         return f"less than a {unit[:-1]}"
-    else:
-        return f"{value} {unit}"
+    return f"{value} {unit}"
 
 
 def humanize_delta(delta: relativedelta, precision: str = "seconds", max_units: int = 6) -> str:
@@ -69,14 +68,14 @@ def humanize_delta(delta: relativedelta, precision: str = "seconds", max_units:
     return humanized
 
 
-def time_since(past_datetime: datetime.datetime, precision: str = "seconds", max_units: int = 6) -> str:
+def time_since(past_datetime: datetime, precision: str = "seconds", max_units: int = 6) -> str:
     """
     Takes a datetime and returns a human-readable string that describes how long ago that datetime was.
 
     precision specifies the smallest unit of time to include (e.g. "seconds", "minutes").
     max_units specifies the maximum number of units of time to include (e.g. 1 may include days but not hours).
     """
-    now = datetime.datetime.utcnow()
+    now = datetime.now(tz=UTC)
     delta = abs(relativedelta(now, past_datetime))
 
     humanized = humanize_delta(delta, precision, max_units)
diff --git a/poetry.lock b/poetry.lock
index 2e3c6565..c904c95e 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -187,22 +187,22 @@ files = [
 
 [[package]]
 name = "attrs"
-version = "22.2.0"
+version = "23.1.0"
 description = "Classes Without Boilerplate"
 category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 files = [
-    {file = "attrs-22.2.0-py3-none-any.whl", hash = "sha256:29e95c7f6778868dbd49170f98f8818f78f3dc5e0e37c0b1f474e3561b240836"},
-    {file = "attrs-22.2.0.tar.gz", hash = "sha256:c9227bfc2f01993c03f68db37d1d15c9690188323c067c641f1a35ca58185f99"},
+    {file = "attrs-23.1.0-py3-none-any.whl", hash = "sha256:1f28b4522cdc2fb4256ac1a020c78acf9cba2c6b461ccd2c126f3aa8e8335d04"},
+    {file = "attrs-23.1.0.tar.gz", hash = "sha256:6279836d581513a26f1bf235f9acd333bc9115683f14f7e8fae46c98fc50e015"},
 ]
 
 [package.extras]
-cov = ["attrs[tests]", "coverage-enable-subprocess", "coverage[toml] (>=5.3)"]
-dev = ["attrs[docs,tests]"]
-docs = ["furo", "myst-parser", "sphinx", "sphinx-notfound-page", "sphinxcontrib-towncrier", "towncrier", "zope.interface"]
-tests = ["attrs[tests-no-zope]", "zope.interface"]
-tests-no-zope = ["cloudpickle", "cloudpickle", "hypothesis", "hypothesis", "mypy (>=0.971,<0.990)", "mypy (>=0.971,<0.990)", "pympler", "pympler", "pytest (>=4.3.0)", "pytest (>=4.3.0)", "pytest-mypy-plugins", "pytest-mypy-plugins", "pytest-xdist[psutil]", "pytest-xdist[psutil]"]
+cov = ["attrs[tests]", "coverage[toml] (>=5.3)"]
+dev = ["attrs[docs,tests]", "pre-commit"]
+docs = ["furo", "myst-parser", "sphinx", "sphinx-notfound-page", "sphinxcontrib-towncrier", "towncrier", "zope-interface"]
+tests = ["attrs[tests-no-zope]", "zope-interface"]
+tests-no-zope = ["cloudpickle", "hypothesis", "mypy (>=1.1.1)", "pympler", "pytest (>=4.3.0)", "pytest-mypy-plugins", "pytest-xdist[psutil]"]
 
 [[package]]
 name = "beautifulsoup4"
@@ -225,14 +225,14 @@ lxml = ["lxml"]
 
 [[package]]
 name = "certifi"
-version = "2022.12.7"
+version = "2023.5.7"
 description = "Python package for providing Mozilla's CA Bundle."
 category = "main"
 optional = false
 python-versions = ">=3.6"
 files = [
-    {file = "certifi-2022.12.7-py3-none-any.whl", hash = "sha256:4ad3232f5e926d6718ec31cfc1fcadfde020920e278684144551c91769c7bc18"},
-    {file = "certifi-2022.12.7.tar.gz", hash = "sha256:35824b4c3a97115964b408844d64aa14db1cc518f6562e8d7261699d1350a9e3"},
+    {file = "certifi-2023.5.7-py3-none-any.whl", hash = "sha256:c6c2e98f5c7869efca1f8916fed228dd91539f9f1b444c314c06eef02980c716"},
+    {file = "certifi-2023.5.7.tar.gz", hash = "sha256:0f0d56dc5a6ad56fd4ba36484d6cc34451e1c6548c61daad8c320169f91eddc7"},
 ]
 
 [[package]]
@@ -326,100 +326,87 @@ files = [
 
 [[package]]
 name = "charset-normalizer"
-version = "3.0.1"
+version = "3.1.0"
 description = "The Real First Universal Charset Detector. Open, modern and actively maintained alternative to Chardet."
 category = "main"
 optional = false
-python-versions = "*"
-files = [
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-    {file = "charset_normalizer-3.0.1-cp310-cp310-macosx_10_9_universal2.whl", hash = "sha256:88600c72ef7587fe1708fd242b385b6ed4b8904976d5da0893e31df8b3480cb6"},
-    {file = "charset_normalizer-3.0.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:c75ffc45f25324e68ab238cb4b5c0a38cd1c3d7f1fb1f72b5541de469e2247db"},
-    {file = "charset_normalizer-3.0.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:db72b07027db150f468fbada4d85b3b2729a3db39178abf5c543b784c1254539"},
-    {file = "charset_normalizer-3.0.1-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:62595ab75873d50d57323a91dd03e6966eb79c41fa834b7a1661ed043b2d404d"},
-    {file = "charset_normalizer-3.0.1-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:ff6f3db31555657f3163b15a6b7c6938d08df7adbfc9dd13d9d19edad678f1e8"},
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+    {file = "charset_normalizer-3.1.0-cp39-cp39-musllinux_1_1_s390x.whl", hash = "sha256:0be65ccf618c1e7ac9b849c315cc2e8a8751d9cfdaa43027d4f6624bd587ab7e"},
+    {file = "charset_normalizer-3.1.0-cp39-cp39-musllinux_1_1_x86_64.whl", hash = "sha256:53d0a3fa5f8af98a1e261de6a3943ca631c526635eb5817a87a59d9a57ebf48f"},
+    {file = "charset_normalizer-3.1.0-cp39-cp39-win32.whl", hash = "sha256:a04f86f41a8916fe45ac5024ec477f41f886b3c435da2d4e3d2709b22ab02af1"},
+    {file = "charset_normalizer-3.1.0-cp39-cp39-win_amd64.whl", hash = "sha256:830d2948a5ec37c386d3170c483063798d7879037492540f10a475e3fd6f244b"},
+    {file = "charset_normalizer-3.1.0-py3-none-any.whl", hash = "sha256:3d9098b479e78c85080c98e1e35ff40b4a31d8953102bb0fd7d1b6f8a2111a3d"},
 ]
 
 [[package]]
@@ -454,14 +441,14 @@ cron = ["capturer (>=2.4)"]
 
 [[package]]
 name = "discord-py"
-version = "2.2.2"
+version = "2.2.3"
 description = "A Python wrapper for the Discord API"
 category = "main"
 optional = false
 python-versions = ">=3.8.0"
 files = [
-    {file = "discord.py-2.2.2-py3-none-any.whl", hash = "sha256:38fc52a784727b8e5e5749267089400035b187a009028eddfabeb182abcc6d52"},
-    {file = "discord.py-2.2.2.tar.gz", hash = "sha256:b9944056bcb5711b2d04088848fd004466cf117c15c84fa798bf55470f28275f"},
+    {file = "discord.py-2.2.3-py3-none-any.whl", hash = "sha256:792bdcfe71cfe013c446cf379b2e83e08b5050604322ad6fb592864e63511abd"},
+    {file = "discord.py-2.2.3.tar.gz", hash = "sha256:f9df95795c6f52c5db43b7ab43634993e12ef233288636a759166dd9c134d077"},
 ]
 
 [package.dependencies]
@@ -513,19 +500,19 @@ files = [
 
 [[package]]
 name = "fakeredis"
-version = "2.9.2"
+version = "2.12.0"
 description = "Fake implementation of redis API for testing purposes."
 category = "main"
 optional = false
-python-versions = ">=3.8,<4.0"
+python-versions = ">=3.7,<4.0"
 files = [
-    {file = "fakeredis-2.9.2-py3-none-any.whl", hash = "sha256:35962e0ded572302c4461ad1a40308259cc10b7c546b13228e6d7880bf7b74bb"},
-    {file = "fakeredis-2.9.2.tar.gz", hash = "sha256:3bcc2b5c10d5e03cc5b46697d77c651f48391b506ff931576d2869c7549e2e25"},
+    {file = "fakeredis-2.12.0-py3-none-any.whl", hash = "sha256:13040c67c471edfa4aa941f023d04f0df05f092e81c9f42a7f91d8fe67612386"},
+    {file = "fakeredis-2.12.0.tar.gz", hash = "sha256:9c98be9f31d4b7d610e83ce3a8a3cb0434beedd16125f10475c618df4c52ed10"},
 ]
 
 [package.dependencies]
 lupa = {version = ">=1.14,<2.0", optional = true, markers = "extra == \"lua\""}
-redis = ">=4,<5"
+redis = ">=4"
 sortedcontainers = ">=2.4,<3.0"
 
 [package.extras]
@@ -534,150 +521,19 @@ lua = ["lupa (>=1.14,<2.0)"]
 
 [[package]]
 name = "filelock"
-version = "3.9.0"
+version = "3.12.0"
 description = "A platform independent file lock."
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "filelock-3.9.0-py3-none-any.whl", hash = "sha256:f58d535af89bb9ad5cd4df046f741f8553a418c01a7856bf0d173bbc9f6bd16d"},
-    {file = "filelock-3.9.0.tar.gz", hash = "sha256:7b319f24340b51f55a2bf7a12ac0755a9b03e718311dac567a0f4f7fabd2f5de"},
-]
-
-[package.extras]
-docs = ["furo (>=2022.12.7)", "sphinx (>=5.3)", "sphinx-autodoc-typehints (>=1.19.5)"]
-testing = ["covdefaults (>=2.2.2)", "coverage (>=7.0.1)", "pytest (>=7.2)", "pytest-cov (>=4)", "pytest-timeout (>=2.1)"]
-
-[[package]]
-name = "flake8"
-version = "6.0.0"
-description = "the modular source code checker: pep8 pyflakes and co"
-category = "dev"
-optional = false
-python-versions = ">=3.8.1"
-files = [
-    {file = "flake8-6.0.0-py2.py3-none-any.whl", hash = "sha256:3833794e27ff64ea4e9cf5d410082a8b97ff1a06c16aa3d2027339cd0f1195c7"},
-    {file = "flake8-6.0.0.tar.gz", hash = "sha256:c61007e76655af75e6785a931f452915b371dc48f56efd765247c8fe68f2b181"},
-]
-
-[package.dependencies]
-mccabe = ">=0.7.0,<0.8.0"
-pycodestyle = ">=2.10.0,<2.11.0"
-pyflakes = ">=3.0.0,<3.1.0"
-
-[[package]]
-name = "flake8-annotations"
-version = "3.0.0"
-description = "Flake8 Type Annotation Checks"
-category = "dev"
-optional = false
-python-versions = ">=3.8.1,<4.0.0"
-files = [
-    {file = "flake8_annotations-3.0.0-py3-none-any.whl", hash = "sha256:ea927d31016515e9aa6e256651d74baeeee6fa4ad3f8383715ec5c0460a4c225"},
-    {file = "flake8_annotations-3.0.0.tar.gz", hash = "sha256:88c8b35a0db10b9a92be69ed3f81494509a18db1c3162551e57bc0fc35fab065"},
-]
-
-[package.dependencies]
-attrs = ">=21.4"
-flake8 = ">=5.0"
-
-[[package]]
-name = "flake8-bugbear"
-version = "23.3.23"
-description = "A plugin for flake8 finding likely bugs and design problems in your program. Contains warnings that don't belong in pyflakes and pycodestyle."
-category = "dev"
-optional = false
-python-versions = ">=3.8.1"
-files = [
-    {file = "flake8-bugbear-23.3.23.tar.gz", hash = "sha256:ea565bdb87b96b56dc499edd6cc3ba7f695373d902a5f56c989b74fad7c7719d"},
-    {file = "flake8_bugbear-23.3.23-py3-none-any.whl", hash = "sha256:8a218d13abd6904800970381057ce8e72cde8eea743240c4ef3ede4dd0bc9cfb"},
-]
-
-[package.dependencies]
-attrs = ">=19.2.0"
-flake8 = ">=6.0.0"
-
-[package.extras]
-dev = ["coverage", "hypothesis", "hypothesmith (>=0.2)", "pre-commit", "pytest", "tox"]
-
-[[package]]
-name = "flake8-docstrings"
-version = "1.7.0"
-description = "Extension for flake8 which uses pydocstyle to check docstrings"
-category = "dev"
-optional = false
-python-versions = ">=3.7"
-files = [
-    {file = "flake8_docstrings-1.7.0-py2.py3-none-any.whl", hash = "sha256:51f2344026da083fc084166a9353f5082b01f72901df422f74b4d953ae88ac75"},
-    {file = "flake8_docstrings-1.7.0.tar.gz", hash = "sha256:4c8cc748dc16e6869728699e5d0d685da9a10b0ea718e090b1ba088e67a941af"},
-]
-
-[package.dependencies]
-flake8 = ">=3"
-pydocstyle = ">=2.1"
-
-[[package]]
-name = "flake8-isort"
-version = "6.0.0"
-description = "flake8 plugin that integrates isort ."
-category = "dev"
-optional = false
-python-versions = ">=3.7"
-files = [
-    {file = "flake8-isort-6.0.0.tar.gz", hash = "sha256:537f453a660d7e903f602ecfa36136b140de279df58d02eb1b6a0c84e83c528c"},
-    {file = "flake8_isort-6.0.0-py3-none-any.whl", hash = "sha256:aa0cac02a62c7739e370ce6b9c31743edac904bae4b157274511fc8a19c75bbc"},
+    {file = "filelock-3.12.0-py3-none-any.whl", hash = "sha256:ad98852315c2ab702aeb628412cbf7e95b7ce8c3bf9565670b4eaecf1db370a9"},
+    {file = "filelock-3.12.0.tar.gz", hash = "sha256:fc03ae43288c013d2ea83c8597001b1129db351aad9c57fe2409327916b8e718"},
 ]
 
-[package.dependencies]
-flake8 = "*"
-isort = ">=5.0.0,<6"
-
 [package.extras]
-test = ["pytest"]
-
-[[package]]
-name = "flake8-string-format"
-version = "0.3.0"
-description = "string format checker, plugin for flake8"
-category = "dev"
-optional = false
-python-versions = "*"
-files = [
-    {file = "flake8-string-format-0.3.0.tar.gz", hash = "sha256:65f3da786a1461ef77fca3780b314edb2853c377f2e35069723348c8917deaa2"},
-    {file = "flake8_string_format-0.3.0-py2.py3-none-any.whl", hash = "sha256:812ff431f10576a74c89be4e85b8e075a705be39bc40c4b4278b5b13e2afa9af"},
-]
-
-[package.dependencies]
-flake8 = "*"
-
-[[package]]
-name = "flake8-tidy-imports"
-version = "4.8.0"
-description = "A flake8 plugin that helps you write tidier imports."
-category = "dev"
-optional = false
-python-versions = ">=3.7"
-files = [
-    {file = "flake8-tidy-imports-4.8.0.tar.gz", hash = "sha256:df44f9c841b5dfb3a7a1f0da8546b319d772c2a816a1afefcce43e167a593d83"},
-    {file = "flake8_tidy_imports-4.8.0-py3-none-any.whl", hash = "sha256:25bd9799358edefa0e010ce2c587b093c3aba942e96aeaa99b6d0500ae1bf09c"},
-]
-
-[package.dependencies]
-flake8 = ">=3.8.0"
-
-[[package]]
-name = "flake8-todo"
-version = "0.7"
-description = "TODO notes checker, plugin for flake8"
-category = "dev"
-optional = false
-python-versions = "*"
-files = [
-    {file = "flake8-todo-0.7.tar.gz", hash = "sha256:6e4c5491ff838c06fe5a771b0e95ee15fc005ca57196011011280fc834a85915"},
-]
-
-[package.dependencies]
-pycodestyle = ">=2.0.0,<3.0.0"
+docs = ["furo (>=2023.3.27)", "sphinx (>=6.1.3)", "sphinx-autodoc-typehints (>=1.23,!=1.23.4)"]
+testing = ["covdefaults (>=2.3)", "coverage (>=7.2.3)", "diff-cover (>=7.5)", "pytest (>=7.3.1)", "pytest-cov (>=4)", "pytest-mock (>=3.10)", "pytest-timeout (>=2.1)"]
 
 [[package]]
 name = "frozenlist"
@@ -780,14 +636,14 @@ pyreadline3 = {version = "*", markers = "sys_platform == \"win32\" and python_ve
 
 [[package]]
 name = "identify"
-version = "2.5.18"
+version = "2.5.24"
 description = "File identification library for Python"
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "identify-2.5.18-py2.py3-none-any.whl", hash = "sha256:93aac7ecf2f6abf879b8f29a8002d3c6de7086b8c28d88e1ad15045a15ab63f9"},
-    {file = "identify-2.5.18.tar.gz", hash = "sha256:89e144fa560cc4cffb6ef2ab5e9fb18ed9f9b3cb054384bab4b95c12f6c309fe"},
+    {file = "identify-2.5.24-py2.py3-none-any.whl", hash = "sha256:986dbfb38b1140e763e413e6feb44cd731faf72d1909543178aa79b0e258265d"},
+    {file = "identify-2.5.24.tar.gz", hash = "sha256:0aac67d5b4812498056d28a9a512a483f5085cc28640b02b258a59dac34301d4"},
 ]
 
 [package.extras]
@@ -1002,18 +858,6 @@ htmlsoup = ["BeautifulSoup4"]
 source = ["Cython (>=0.29.7)"]
 
 [[package]]
-name = "mccabe"
-version = "0.7.0"
-description = "McCabe checker, plugin for flake8"
-category = "dev"
-optional = false
-python-versions = ">=3.6"
-files = [
-    {file = "mccabe-0.7.0-py2.py3-none-any.whl", hash = "sha256:6c2d30ab6be0e4a46919781807b4f0d834ebdd6c6e3dca0bda5a15f863427b6e"},
-    {file = "mccabe-0.7.0.tar.gz", hash = "sha256:348e0240c33b60bbdf4e523192ef919f28cb2c3d7d5c7794f74009290f236325"},
-]
-
-[[package]]
 name = "mslex"
 version = "0.3.0"
 description = "shlex for windows"
@@ -1125,21 +969,6 @@ files = [
 setuptools = "*"
 
 [[package]]
-name = "pep8-naming"
-version = "0.13.3"
-description = "Check PEP-8 naming conventions, plugin for flake8"
-category = "dev"
-optional = false
-python-versions = ">=3.7"
-files = [
-    {file = "pep8-naming-0.13.3.tar.gz", hash = "sha256:1705f046dfcd851378aac3be1cd1551c7c1e5ff363bacad707d43007877fa971"},
-    {file = "pep8_naming-0.13.3-py3-none-any.whl", hash = "sha256:1a86b8c71a03337c97181917e2b472f0f5e4ccb06844a0d6f0a33522549e7a80"},
-]
-
-[package.dependencies]
-flake8 = ">=5.0.0"
-
-[[package]]
 name = "pillow"
 version = "9.5.0"
 description = "Python Imaging Library (Fork)"
@@ -1221,14 +1050,14 @@ tests = ["check-manifest", "coverage", "defusedxml", "markdown2", "olefile", "pa
 
 [[package]]
 name = "pip-licenses"
-version = "4.2.0"
+version = "4.3.1"
 description = "Dump the software license list of Python packages installed with pip."
 category = "dev"
 optional = false
 python-versions = "~=3.8"
 files = [
-    {file = "pip-licenses-4.2.0.tar.gz", hash = "sha256:cabf1d83391c42278f1887a76555246bfcd9478c53be26e01e93b66d364f18a9"},
-    {file = "pip_licenses-4.2.0-py3-none-any.whl", hash = "sha256:b6e057e359c0c4c927b7f70b43c27f06d9732a7830bb0aa14ac01f7281d3a972"},
+    {file = "pip-licenses-4.3.1.tar.gz", hash = "sha256:80236ae03036f0edccae57489de3932aa93984a7b552f4fd47399b08793918ff"},
+    {file = "pip_licenses-4.3.1-py3-none-any.whl", hash = "sha256:1e6652f7f3bd173e0a3551202e19518b21ac1d5ab1a2b54e08d96ee67146f9ca"},
 ]
 
 [package.dependencies]
@@ -1239,30 +1068,30 @@ test = ["docutils", "mypy", "pytest-cov", "pytest-pycodestyle", "pytest-runner"]
 
 [[package]]
 name = "platformdirs"
-version = "3.1.0"
+version = "3.5.0"
 description = "A small Python package for determining appropriate platform-specific dirs, e.g. a \"user data dir\"."
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "platformdirs-3.1.0-py3-none-any.whl", hash = "sha256:13b08a53ed71021350c9e300d4ea8668438fb0046ab3937ac9a29913a1a1350a"},
-    {file = "platformdirs-3.1.0.tar.gz", hash = "sha256:accc3665857288317f32c7bebb5a8e482ba717b474f3fc1d18ca7f9214be0cef"},
+    {file = "platformdirs-3.5.0-py3-none-any.whl", hash = "sha256:47692bc24c1958e8b0f13dd727307cff1db103fca36399f457da8e05f222fdc4"},
+    {file = "platformdirs-3.5.0.tar.gz", hash = "sha256:7954a68d0ba23558d753f73437c55f89027cf8f5108c19844d4b82e5af396335"},
 ]
 
 [package.extras]
-docs = ["furo (>=2022.12.7)", "proselint (>=0.13)", "sphinx (>=6.1.3)", "sphinx-autodoc-typehints (>=1.22,!=1.23.4)"]
-test = ["appdirs (==1.4.4)", "covdefaults (>=2.2.2)", "pytest (>=7.2.1)", "pytest-cov (>=4)", "pytest-mock (>=3.10)"]
+docs = ["furo (>=2023.3.27)", "proselint (>=0.13)", "sphinx (>=6.1.3)", "sphinx-autodoc-typehints (>=1.23,!=1.23.4)"]
+test = ["appdirs (==1.4.4)", "covdefaults (>=2.3)", "pytest (>=7.3.1)", "pytest-cov (>=4)", "pytest-mock (>=3.10)"]
 
 [[package]]
 name = "pre-commit"
-version = "3.2.2"
+version = "3.3.1"
 description = "A framework for managing and maintaining multi-language pre-commit hooks."
 category = "dev"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "pre_commit-3.2.2-py2.py3-none-any.whl", hash = "sha256:0b4210aea813fe81144e87c5a291f09ea66f199f367fa1df41b55e1d26e1e2b4"},
-    {file = "pre_commit-3.2.2.tar.gz", hash = "sha256:5b808fcbda4afbccf6d6633a56663fed35b6c2bc08096fd3d47ce197ac351d9d"},
+    {file = "pre_commit-3.3.1-py2.py3-none-any.whl", hash = "sha256:218e9e3f7f7f3271ebc355a15598a4d3893ad9fc7b57fe446db75644543323b9"},
+    {file = "pre_commit-3.3.1.tar.gz", hash = "sha256:733f78c9a056cdd169baa6cd4272d51ecfda95346ef8a89bf93712706021b907"},
 ]
 
 [package.dependencies]
@@ -1274,14 +1103,14 @@ virtualenv = ">=20.10.0"
 
 [[package]]
 name = "prettytable"
-version = "3.6.0"
+version = "3.7.0"
 description = "A simple Python library for easily displaying tabular data in a visually appealing ASCII table format"
 category = "dev"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "prettytable-3.6.0-py3-none-any.whl", hash = "sha256:3b767129491767a3a5108e6f305cbaa650f8020a7db5dfe994a2df7ef7bad0fe"},
-    {file = "prettytable-3.6.0.tar.gz", hash = "sha256:2e0026af955b4ea67b22122f310b90eae890738c08cb0458693a49b6221530ac"},
+    {file = "prettytable-3.7.0-py3-none-any.whl", hash = "sha256:f4aaf2ed6e6062a82fd2e6e5289bbbe705ec2788fe401a3a1f62a1cea55526d2"},
+    {file = "prettytable-3.7.0.tar.gz", hash = "sha256:ef8334ee40b7ec721651fc4d37ecc7bb2ef55fde5098d994438f0dfdaa385c0c"},
 ]
 
 [package.dependencies]
@@ -1292,26 +1121,26 @@ tests = ["pytest", "pytest-cov", "pytest-lazy-fixture"]
 
 [[package]]
 name = "psutil"
-version = "5.9.4"
+version = "5.9.5"
 description = "Cross-platform lib for process and system monitoring in Python."
 category = "dev"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
 files = [
-    {file = "psutil-5.9.4-cp27-cp27m-macosx_10_9_x86_64.whl", hash = "sha256:c1ca331af862803a42677c120aff8a814a804e09832f166f226bfd22b56feee8"},
-    {file = "psutil-5.9.4-cp27-cp27m-manylinux2010_i686.whl", hash = "sha256:68908971daf802203f3d37e78d3f8831b6d1014864d7a85937941bb35f09aefe"},
-    {file = "psutil-5.9.4-cp27-cp27m-manylinux2010_x86_64.whl", hash = "sha256:3ff89f9b835100a825b14c2808a106b6fdcc4b15483141482a12c725e7f78549"},
-    {file = "psutil-5.9.4-cp27-cp27m-win32.whl", hash = "sha256:852dd5d9f8a47169fe62fd4a971aa07859476c2ba22c2254d4a1baa4e10b95ad"},
-    {file = "psutil-5.9.4-cp27-cp27m-win_amd64.whl", hash = "sha256:9120cd39dca5c5e1c54b59a41d205023d436799b1c8c4d3ff71af18535728e94"},
-    {file = "psutil-5.9.4-cp27-cp27mu-manylinux2010_i686.whl", hash = "sha256:6b92c532979bafc2df23ddc785ed116fced1f492ad90a6830cf24f4d1ea27d24"},
-    {file = "psutil-5.9.4-cp27-cp27mu-manylinux2010_x86_64.whl", hash = "sha256:efeae04f9516907be44904cc7ce08defb6b665128992a56957abc9b61dca94b7"},
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 ]
 
 [package.extras]
@@ -1386,18 +1215,6 @@ cffi = ">=1.5.0"
 idna = ["idna (>=2.1)"]
 
 [[package]]
-name = "pycodestyle"
-version = "2.10.0"
-description = "Python style guide checker"
-category = "dev"
-optional = false
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-
-[[package]]
 name = "pycparser"
 version = "2.21"
 description = "C parser in Python"
@@ -1410,55 +1227,79 @@ files = [
 ]
 
 [[package]]
-name = "pydis-core"
-version = "9.5.1"
-description = "PyDis core provides core functionality and utility to the bots of the Python Discord community."
+name = "pydantic"
+version = "1.10.7"
+description = "Data validation and settings management using python type hints"
 category = "main"
 optional = false
-python-versions = ">=3.10.0,<3.12.0"
+python-versions = ">=3.7"
 files = [
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 ]
 
 [package.dependencies]
-aiodns = "3.0.0"
-async-rediscache = {version = "1.0.0rc2", extras = ["fakeredis"], optional = true, markers = "extra == \"async-rediscache\""}
-"discord.py" = "2.2.2"
-statsd = "4.0.1"
+python-dotenv = {version = ">=0.10.4", optional = true, markers = "extra == \"dotenv\""}
+typing-extensions = ">=4.2.0"
 
 [package.extras]
-async-rediscache = ["async-rediscache[fakeredis] (==1.0.0rc2)"]
+dotenv = ["python-dotenv (>=0.10.4)"]
+email = ["email-validator (>=1.0.3)"]
 
 [[package]]
-name = "pydocstyle"
-version = "6.3.0"
-description = "Python docstring style checker"
-category = "dev"
+name = "pydis-core"
+version = "9.6.0"
+description = "PyDis core provides core functionality and utility to the bots of the Python Discord community."
+category = "main"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.10.0,<3.12.0"
 files = [
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 ]
 
 [package.dependencies]
-snowballstemmer = ">=2.2.0"
+aiodns = "3.0.0"
+async-rediscache = {version = "1.0.0rc2", extras = ["fakeredis"], optional = true, markers = "extra == \"async-rediscache\""}
+"discord.py" = "2.2.3"
+statsd = "4.0.1"
 
 [package.extras]
-toml = ["tomli (>=1.2.3)"]
-
-[[package]]
-name = "pyflakes"
-version = "3.0.1"
-description = "passive checker of Python programs"
-category = "dev"
-optional = false
-python-versions = ">=3.6"
-files = [
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-]
+async-rediscache = ["async-rediscache[fakeredis] (==1.0.0rc2)"]
 
 [[package]]
 name = "pyjokes"
@@ -1507,7 +1348,7 @@ six = ">=1.5"
 name = "python-dotenv"
 version = "1.0.0"
 description = "Read key-value pairs from a .env file and set them as environment variables"
-category = "dev"
+category = "main"
 optional = false
 python-versions = ">=3.8"
 files = [
@@ -1675,38 +1516,65 @@ full = ["numpy"]
 
 [[package]]
 name = "redis"
-version = "4.5.4"
+version = "4.5.5"
 description = "Python client for Redis database and key-value store"
 category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
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 ]
 
 [package.dependencies]
-async-timeout = {version = ">=4.0.2", markers = "python_version <= \"3.11.2\""}
+async-timeout = {version = ">=4.0.2", markers = "python_full_version <= \"3.11.2\""}
 
 [package.extras]
 hiredis = ["hiredis (>=1.0.0)"]
 ocsp = ["cryptography (>=36.0.1)", "pyopenssl (==20.0.1)", "requests (>=2.26.0)"]
 
 [[package]]
+name = "ruff"
+version = "0.0.267"
+description = "An extremely fast Python linter, written in Rust."
+category = "dev"
+optional = false
+python-versions = ">=3.7"
+files = [
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+
+[[package]]
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+version = "1.23.0"
 description = "Python client for Sentry (https://sentry.io)"
 category = "main"
 optional = false
 python-versions = "*"
 files = [
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 [package.dependencies]
 certifi = "*"
-urllib3 = {version = ">=1.26.11", markers = "python_version >= \"3.6\""}
+urllib3 = {version = ">=1.26.11,<2.0.0", markers = "python_version >= \"3.6\""}
 
 [package.extras]
 aiohttp = ["aiohttp (>=3.5)"]
@@ -1718,10 +1586,11 @@ chalice = ["chalice (>=1.16.0)"]
 django = ["django (>=1.8)"]
 falcon = ["falcon (>=1.4)"]
 fastapi = ["fastapi (>=0.79.0)"]
-flask = ["blinker (>=1.1)", "flask (>=0.11)"]
+flask = ["blinker (>=1.1)", "flask (>=0.11)", "markupsafe"]
 grpcio = ["grpcio (>=1.21.1)"]
 httpx = ["httpx (>=0.16.0)"]
 huey = ["huey (>=2)"]
+loguru = ["loguru (>=0.5)"]
 opentelemetry = ["opentelemetry-distro (>=0.35b0)"]
 pure-eval = ["asttokens", "executing", "pure-eval"]
 pymongo = ["pymongo (>=3.1)"]
@@ -1736,14 +1605,14 @@ tornado = ["tornado (>=5)"]
 
 [[package]]
 name = "setuptools"
-version = "67.4.0"
+version = "67.7.2"
 description = "Easily download, build, install, upgrade, and uninstall Python packages"
 category = "dev"
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 python-versions = ">=3.7"
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 ]
 
 [package.extras]
@@ -1764,18 +1633,6 @@ files = [
 ]
 
 [[package]]
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-description = "This package provides 29 stemmers for 28 languages generated from Snowball algorithms."
-category = "dev"
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@@ -1789,14 +1646,14 @@ files = [
 
 [[package]]
 name = "soupsieve"
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+version = "2.4.1"
 description = "A modern CSS selector implementation for Beautiful Soup."
 category = "main"
 optional = false
 python-versions = ">=3.7"
 files = [
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 ]
 
 [[package]]
@@ -1842,15 +1699,27 @@ files = [
 ]
 
 [[package]]
+name = "typing-extensions"
+version = "4.5.0"
+description = "Backported and Experimental Type Hints for Python 3.7+"
+category = "main"
+optional = false
+python-versions = ">=3.7"
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+[[package]]
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 category = "main"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*, !=3.5.*"
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 [package.extras]
@@ -1860,24 +1729,24 @@ socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
 
 [[package]]
 name = "virtualenv"
-version = "20.20.0"
+version = "20.23.0"
 description = "Virtual Python Environment builder"
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 python-versions = ">=3.7"
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-platformdirs = ">=2.4,<4"
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+platformdirs = ">=3.2,<4"
 
 [package.extras]
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 [[package]]
 name = "wcwidth"
@@ -1893,86 +1762,86 @@ files = [
 
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 python-versions = ">=3.7"
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+    {file = "yarl-1.9.2-cp39-cp39-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:b03917871bf859a81ccb180c9a2e6c1e04d2f6a51d953e6a5cdd70c93d4e5a2a"},
+    {file = "yarl-1.9.2-cp39-cp39-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:c1012fa63eb6c032f3ce5d2171c267992ae0c00b9e164efe4d73db818465fac3"},
+    {file = "yarl-1.9.2-cp39-cp39-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:a74dcbfe780e62f4b5a062714576f16c2f3493a0394e555ab141bf0d746bb955"},
+    {file = "yarl-1.9.2-cp39-cp39-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:8c56986609b057b4839968ba901944af91b8e92f1725d1a2d77cbac6972b9ed1"},
+    {file = "yarl-1.9.2-cp39-cp39-musllinux_1_1_aarch64.whl", hash = "sha256:2c315df3293cd521033533d242d15eab26583360b58f7ee5d9565f15fee1bef4"},
+    {file = "yarl-1.9.2-cp39-cp39-musllinux_1_1_i686.whl", hash = "sha256:b7232f8dfbd225d57340e441d8caf8652a6acd06b389ea2d3222b8bc89cbfca6"},
+    {file = "yarl-1.9.2-cp39-cp39-musllinux_1_1_ppc64le.whl", hash = "sha256:53338749febd28935d55b41bf0bcc79d634881195a39f6b2f767870b72514caf"},
+    {file = "yarl-1.9.2-cp39-cp39-musllinux_1_1_s390x.whl", hash = "sha256:066c163aec9d3d073dc9ffe5dd3ad05069bcb03fcaab8d221290ba99f9f69ee3"},
+    {file = "yarl-1.9.2-cp39-cp39-musllinux_1_1_x86_64.whl", hash = "sha256:8288d7cd28f8119b07dd49b7230d6b4562f9b61ee9a4ab02221060d21136be80"},
+    {file = "yarl-1.9.2-cp39-cp39-win32.whl", hash = "sha256:b124e2a6d223b65ba8768d5706d103280914d61f5cae3afbc50fc3dfcc016623"},
+    {file = "yarl-1.9.2-cp39-cp39-win_amd64.whl", hash = "sha256:61016e7d582bc46a5378ffdd02cd0314fb8ba52f40f9cf4d9a5e7dbef88dee18"},
+    {file = "yarl-1.9.2.tar.gz", hash = "sha256:04ab9d4b9f587c06d801c2abfe9317b77cdf996c65a90d5e84ecc45010823571"},
 ]
 
 [package.dependencies]
@@ -1982,4 +1851,4 @@ multidict = ">=4.0"
 [metadata]
 lock-version = "2.0"
 python-versions = "3.11.*"
-content-hash = "a67fc2b1b3a3a2bdd858c160ffcc1a1b74532f2a1a4ab4659b62687d43934d7d"
+content-hash = "dca820268faec5488f1769c5acbeb43593514061c835f5b648866ac4072a2c9e"
diff --git a/pyproject.toml b/pyproject.toml
index e99c87a4..ae3b3245 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -9,14 +9,14 @@ license = "MIT"
 python = "3.11.*"
 
 # See https://bot-core.pythondiscord.com/ for docs.
-pydis_core = { version = "9.5.1", extras = ["async-rediscache"] }
+pydis_core = { version = "9.6.0", extras = ["async-rediscache"] }
 
 aiodns = "3.0.0"
 rapidfuzz = "3.0.0"
 arrow = "1.2.3"
 beautifulsoup4 = "4.12.2"
 pillow = "9.5.0"
-sentry-sdk = "1.21.0"
+sentry-sdk = "1.23.0"
 PyYAML = "6.0"
 emojis = "0.7.0"
 coloredlogs = "15.0.1"
@@ -24,20 +24,15 @@ colorama = { version = "0.4.6", markers = "sys_platform == 'win32'" }
 lxml = "4.9.2"
 emoji = "2.2.0"
 pyjokes = "0.6.0"
+pydantic = { version = "1.10.7", extras = ["dotenv"]}
+
 
 [tool.poetry.dev-dependencies]
-flake8 = "6.0.0"
-flake8-annotations = "3.0.0"
-flake8-bugbear = "23.3.23"
-flake8-docstrings = "1.7.0"
-flake8-string-format = "0.3.0"
-flake8-tidy-imports = "4.8.0"
-flake8-todo = "0.7"
-flake8-isort = "6.0.0"
-pep8-naming = "0.13.3"
-pip-licenses = "4.2.0"
-pre-commit = "3.2.2"
+isort = "5.12.0"
+pip-licenses = "4.3.1"
+pre-commit = "3.3.1"
 python-dotenv = "1.0.0"
+ruff = "0.0.267"
 taskipy = "1.10.4"
 
 [tool.taskipy.tasks]
@@ -58,3 +53,21 @@ combine_as_imports = true
 line_length = 120
 atomic = true
 known_first_party = ["bot"]
+
+[tool.ruff]
+target-version = "py311"
+extend-exclude = [".cache"]
+ignore = [
+    "ANN002", "ANN003", "ANN101", "ANN102", "ANN204", "ANN206", "ANN401",
+    "B904",
+    "C401", "C408",
+    "D100", "D104", "D105", "D107", "D203", "D212", "D214", "D215", "D301",
+    "D400", "D401", "D402", "D404", "D405", "D406", "D407", "D408", "D409", "D410", "D411", "D412", "D413", "D414", "D416", "D417",
+    "E731",
+    "RET504",
+    "RUF005",
+    "S311",
+    "SIM102", "SIM108",
+]
+line-length = 120
+select = ["ANN", "B", "C4", "D", "DTZ", "E", "F", "ISC", "INT", "N", "PGH", "PIE", "Q", "RET", "RSE", "RUF", "S", "SIM", "T20", "TID", "UP", "W"]
diff --git a/tox.ini b/tox.ini
deleted file mode 100644
index 7906e6d9..00000000
--- a/tox.ini
+++ /dev/null
@@ -1,26 +0,0 @@
-[flake8]
-max-line-length=120
-application_import_names=bot
-docstring-convention=all
-extend-ignore=
-    P102,B311,W503,E226,S311,
-    # Missing Docstrings
-    D100,D104,D105,D107,
-    # Docstring Whitespace
-    D203,D212,D214,D215,
-    # Docstring Quotes
-    D301,D302,
-    # Docstring Content
-    D400,D401,D402,D404,D405,D406,D407,D408,D409,D410,D411,D412,D413,D414,D416,D417,
-    # Type Annotations
-    ANN002,ANN003,ANN101,ANN102,ANN204,ANN206,
-    # Binary operators over multiple lines
-    W504,
-exclude=
-    __pycache__,.cache,
-    venv,.venv,
-    tests,
-per-file-ignores =
-    # Don't require docstrings in constants
-    constants.py:D101
-import-order-style=pycharm