Merge branch 'main' into undeprecate-bookmark

21 files changed, 225 insertions, 224 deletions

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.