diff --git a/src/common/database.py b/src/common/database.py
index 0c469af..58dadfe 100644
--- a/src/common/database.py
+++ b/src/common/database.py
@@ -5,7 +5,6 @@
 import shelve
 import shutil
 import threading
-from typing import Union
 
 # lib imports
 import git
@@ -25,7 +24,7 @@
 
 
 class Database:
-    def __init__(self, db_name: str, db_dir: Union[str, Path] = data_dir, use_git: bool = True):
+    def __init__(self, db_name: str, db_dir: str | Path = data_dir, use_git: bool = True):
         self.db_name = db_name
         self.db_dir = db_dir
         self.repo = None
diff --git a/src/common/rank.py b/src/common/rank.py
index c20b6b1..412dbb2 100644
--- a/src/common/rank.py
+++ b/src/common/rank.py
@@ -5,7 +5,7 @@
 import random
 import threading
 import time
-from typing import Dict, List, Optional, Tuple, Union
+from typing import Dict, List, Optional, Tuple
 
 # lib imports
 import aiohttp
@@ -60,7 +60,7 @@ def __init__(
         self.last_activity = {}  # Tracks last activity time for cooldowns
 
     @staticmethod
-    def get_community_id(platform: str, user: Union[DiscordUser, RedditUser]) -> Optional[Union[int, str]]:
+    def get_community_id(platform: str, user: DiscordUser | RedditUser) -> int | str | None:
         """
         Get the community ID for a user based on platform.
 
@@ -68,12 +68,12 @@ def get_community_id(platform: str, user: Union[DiscordUser, RedditUser]) -> Opt
         ----------
         platform : str
             Platform identifier ('discord' or 'reddit')
-        user : Union[DiscordUser, RedditUser]
+        user : DiscordUser | RedditUser
             Discord or Reddit user object
 
         Returns
         -------
-        Union[int, str]
+        int | str
             Community ID (guild_id for Discord, subreddit_id for Reddit)
         """
         if platform == 'discord':
@@ -138,7 +138,7 @@ def calculate_xp_for_level(level: int) -> int:
     def get_rank_data(
             self,
             platform: str,
-            user: Union[DiscordUser, RedditUser],
+            user: DiscordUser | RedditUser,
             create_if_not_exists: bool = False,
     ) -> dict:
         """
@@ -148,7 +148,7 @@ def get_rank_data(
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        user : Union[DiscordUser, RedditUser]
+        user : DiscordUser | RedditUser
             Discord or Reddit user object
         create_if_not_exists : bool
             If True, create a new user entry if it doesn't exist
@@ -189,7 +189,7 @@ def get_rank_data(
 
         return user_data
 
-    def update_rank_data(self, platform: str, user: Union[DiscordUser, RedditUser], data: dict) -> dict:
+    def update_rank_data(self, platform: str, user: DiscordUser | RedditUser, data: dict) -> dict:
         """
         Update rank data for a user.
 
@@ -197,7 +197,7 @@ def update_rank_data(self, platform: str, user: Union[DiscordUser, RedditUser],
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        user : Union[DiscordUser, RedditUser]
+        user : DiscordUser | RedditUser
             Discord or Reddit user object
         data : dict
             New data to update
@@ -219,7 +219,7 @@ def update_rank_data(self, platform: str, user: Union[DiscordUser, RedditUser],
             data=data,
         )
 
-    def award_xp(self, platform: str, user: Union[DiscordUser, RedditUser]) -> Optional[dict]:
+    def award_xp(self, platform: str, user: DiscordUser | RedditUser) -> Optional[dict]:
         """
         Award XP to a user with cooldown enforcement.
 
@@ -227,7 +227,7 @@ def award_xp(self, platform: str, user: Union[DiscordUser, RedditUser]) -> Optio
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        user : Union[DiscordUser, RedditUser]
+        user : DiscordUser | RedditUser
             Discord or Reddit user object
 
         Returns
@@ -287,8 +287,8 @@ def award_xp(self, platform: str, user: Union[DiscordUser, RedditUser]) -> Optio
     def get_leaderboard(
             self,
             platform: str,
-            user: Optional[Union[DiscordUser, RedditUser]] = None,
-            community_id: Optional[Union[int, str]] = None,
+            user: DiscordUser | RedditUser | None = None,
+            community_id: int | str | None = None,
             limit: int = 100,
             offset: int = 0,
     ) -> List[dict]:
@@ -299,9 +299,9 @@ def get_leaderboard(
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        user : Optional[Union[DiscordUser, RedditUser]]
+        user : DiscordUser | RedditUser | None
             User object to determine community_id if not explicitly provided
-        community_id : Optional[Union[int, str]]
+        community_id : int | str | None
             Community identifier (guild_id for Discord, subreddit_id for Reddit)
         limit : int
             Maximum number of entries to return
@@ -338,7 +338,7 @@ def get_leaderboard(
 
         return leaderboard
 
-    def get_user_rank_position(self, platform: str, user: Union[DiscordUser, RedditUser]) -> Optional[int]:
+    def get_user_rank_position(self, platform: str, user: DiscordUser | RedditUser) -> Optional[int]:
         """
         Get the exact rank position of a user on the leaderboard without any limits.
 
@@ -346,7 +346,7 @@ def get_user_rank_position(self, platform: str, user: Union[DiscordUser, RedditU
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        user : Union[DiscordUser, RedditUser]
+        user : DiscordUser | RedditUser
             Discord or Reddit user object
 
         Returns
@@ -377,8 +377,8 @@ def get_user_rank_position(self, platform: str, user: Union[DiscordUser, RedditU
     def get_migration_status(
             self,
             platform: str,
-            community_id: Union[int, str],
-            source_id: Union[int, str],
+            community_id: int | str,
+            source_id: int | str,
     ) -> Optional[dict]:
         """
         Check if migration has already been performed for a specific source.
@@ -387,9 +387,9 @@ def get_migration_status(
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id or subreddit_id)
-        source_id : Union[int, str]
+        source_id : int | str
             Source identifier (e.g., guild_id for Mee6)
 
         Returns
@@ -406,8 +406,8 @@ def get_migration_status(
     def set_migration_completed(
             self,
             platform: str,
-            community_id: Union[int, str],
-            source_id: Union[int, str],
+            community_id: int | str,
+            source_id: int | str,
             stats: dict,
     ) -> dict:
         """
@@ -417,9 +417,9 @@ def set_migration_completed(
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id or subreddit_id)
-        source_id : Union[int, str]
+        source_id : int | str
             Source identifier (e.g., guild_id for Mee6)
         stats : dict
             Migration statistics
@@ -441,7 +441,7 @@ def migrate_from_reddit_database(
             reddit_bot,
             reddit_db,
             community_id: str,
-    ) -> Dict[str, Union[int, str]]:
+    ) -> Dict[str, int | str]:
         """
         Migrate user data from Reddit database.
 
@@ -458,7 +458,7 @@ def migrate_from_reddit_database(
 
         Returns
         -------
-        Dict[str, Union[int, str]]
+        Dict[str, int | str]
             Migration statistics
         """
         # Acquire migration lock to prevent concurrent migrations
@@ -600,7 +600,7 @@ def _do_reddit_migration(
             reddit_bot,
             reddit_db,
             community_id: str,
-    ) -> Dict[str, Union[int, str]]:
+    ) -> Dict[str, int | str]:
         """Internal method that performs the actual Reddit migration."""
         total_submissions = 0
         total_comments = 0
@@ -681,7 +681,7 @@ def _do_reddit_migration(
         logger.info(f"Reddit migration completed with stats: {stats}")
         return stats
 
-    async def migrate_from_mee6(self, guild_id: int) -> Dict[str, Union[int, str]]:
+    async def migrate_from_mee6(self, guild_id: int) -> Dict[str, int | str]:
         """
         Migrate user data from Mee6 API.
 
@@ -692,7 +692,7 @@ async def migrate_from_mee6(self, guild_id: int) -> Dict[str, Union[int, str]]:
 
         Returns
         -------
-        Dict[str, Union[int, str]]
+        Dict[str, int | str]
             Migration statistics
         """
         import asyncio
@@ -818,7 +818,7 @@ def _process_mee6_batch(
 
         return new_users, updated_users
 
-    async def _do_mee6_migration(self, guild_id: int) -> Dict[str, Union[int, str]]:
+    async def _do_mee6_migration(self, guild_id: int) -> Dict[str, int | str]:
         """Internal method that performs the actual Mee6 migration."""
         page = 0
         total_users = 0
diff --git a/src/common/rank_database.py b/src/common/rank_database.py
index 8d76da3..2b1b9fc 100644
--- a/src/common/rank_database.py
+++ b/src/common/rank_database.py
@@ -1,5 +1,5 @@
 # standard imports
-from typing import List, Optional, Union
+from typing import List, Optional
 
 # local imports
 from src.common.database import Database
@@ -39,7 +39,7 @@ def _ensure_tables(self):
     def get_community_users(
             self,
             platform: str,
-            community_id: Union[int, str],
+            community_id: int | str,
             search: Optional[str] = None,
     ) -> List[dict]:
         """
@@ -49,7 +49,7 @@ def get_community_users(
         ----------
         platform : str
             Platform identifier ('discord' or 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id for Discord, subreddit_id for Reddit)
         search : Optional[str]
             Optional search string to filter users by username (case-insensitive)
@@ -84,8 +84,8 @@ def get_community_users(
     def get_user_data(
             self,
             platform: str,
-            community_id: Union[int, str],
-            user_id: Union[int, str],
+            community_id: int | str,
+            user_id: int | str,
             create_if_not_exists: bool = False,
     ) -> dict:
         """
@@ -95,9 +95,9 @@ def get_user_data(
         ----------
         platform : str
             Platform identifier ('discord' or 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id for Discord, subreddit_id for Reddit)
-        user_id : Union[int, str]
+        user_id : int | str
             User identifier
         create_if_not_exists : bool
             Whether to create a new user entry if it doesn't exist
@@ -140,8 +140,8 @@ def get_user_data(
     def update_user_data(
             self,
             platform: str,
-            community_id: Union[int, str],
-            user_id: Union[int, str],
+            community_id: int | str,
+            user_id: int | str,
             data: dict,
     ) -> dict:
         """
@@ -151,9 +151,9 @@ def update_user_data(
         ----------
         platform : str
             Platform identifier ('discord' or 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id or subreddit_id)
-        user_id : Union[int, str]
+        user_id : int | str
             User identifier
         data : dict
             New user data
@@ -196,7 +196,7 @@ def update_user_data(
     def get_leaderboard(
             self,
             platform: str,
-            community_id: Union[int, str],
+            community_id: int | str,
             limit: int = 100,
             offset: int = 0,
     ) -> List[dict]:
@@ -207,7 +207,7 @@ def get_leaderboard(
         ----------
         platform : str
             Platform identifier ('discord' or 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id or subreddit_id)
         limit : int
             Maximum number of entries to return
@@ -251,8 +251,8 @@ def get_leaderboard(
     def get_migration_status(
             self,
             platform: str,
-            community_id: Union[int, str],
-            source_id: Union[int, str],
+            community_id: int | str,
+            source_id: int | str,
     ) -> Optional[dict]:
         """
         Check if migration has already been performed for a specific source.
@@ -261,9 +261,9 @@ def get_migration_status(
         ----------
         platform : str
             Platform identifier (e.g., 'discord', 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id or subreddit_id)
-        source_id : Union[int, str]
+        source_id : int | str
             Source identifier (e.g., guild_id for Mee6)
 
         Returns
@@ -285,8 +285,8 @@ def get_migration_status(
 
     def set_migration_completed(
             self, platform: str,
-            community_id: Union[int, str],
-            source_id: Union[int, str],
+            community_id: int | str,
+            source_id: int | str,
             stats: dict,
     ) -> dict:
         """
@@ -296,9 +296,9 @@ def set_migration_completed(
         ----------
         platform : str
             Platform identifier ('discord' or 'reddit')
-        community_id : Union[int, str]
+        community_id : int | str
             Community identifier (guild_id or subreddit_id)
-        source_id : Union[int, str]
+        source_id : int | str
             Source identifier (e.g., guild_id for Mee6)
         stats : dict
             Migration statistics
diff --git a/src/common/sponsors.py b/src/common/sponsors.py
index 793c5d8..37b1033 100644
--- a/src/common/sponsors.py
+++ b/src/common/sponsors.py
@@ -1,7 +1,7 @@
 # standard imports
 import logging
 import os
-from typing import Union
+from typing import Literal
 
 # lib imports
 import requests
@@ -18,13 +18,13 @@
 }
 
 
-def get_github_sponsors() -> Union[dict, False]:
+def get_github_sponsors() -> dict | Literal[False]:
     """
     Get list of GitHub sponsors.
 
     Returns
     -------
-    Union[dict, False]
+    dict | Literal[False]
         JSON response containing the list of sponsors. False if an error occurred.
     """
     token = os.getenv("GITHUB_TOKEN")
diff --git a/src/discord_bot/cogs/fun_commands.py b/src/discord_bot/cogs/fun_commands.py
index 7c88759..4051f7e 100644
--- a/src/discord_bot/cogs/fun_commands.py
+++ b/src/discord_bot/cogs/fun_commands.py
@@ -16,10 +16,12 @@ def __init__(self, bot):
         self.bot = bot
 
     async def get_random_quotes(self) -> list[dict]:
-        async with aiohttp.ClientSession() as session:
-            async with session.get(url='https://app.lizardbyte.dev/uno/random-quotes/games.json') as response:
-                response.raise_for_status()
-                return await response.json()
+        async with (
+            aiohttp.ClientSession() as session,
+            session.get(url='https://app.lizardbyte.dev/uno/random-quotes/games.json') as response,
+        ):
+            response.raise_for_status()
+            return await response.json()
 
     @discord.slash_command(
         name="random",
diff --git a/src/discord_bot/cogs/moderator_commands.py b/src/discord_bot/cogs/moderator_commands.py
index 832d879..0a787b3 100644
--- a/src/discord_bot/cogs/moderator_commands.py
+++ b/src/discord_bot/cogs/moderator_commands.py
@@ -1,6 +1,5 @@
 # standard imports
 import time
-from typing import Union
 
 # lib imports
 import discord
@@ -32,7 +31,7 @@ async def channel_command(
             self,
             ctx: discord.ApplicationContext,
             recommended_channel: Option(
-                Union[discord.ForumChannel, discord.TextChannel],
+                discord.ForumChannel | discord.TextChannel,
                 description=recommended_channel_desc,
                 required=True,
             ),
@@ -45,7 +44,7 @@ async def channel_command(
         ----------
         ctx : discord.ApplicationContext
             Request message context.
-        recommended_channel : Union[discord.ForumChannel, discord.TextChannel]
+        recommended_channel : discord.ForumChannel | discord.TextChannel
             The recommended channel to move discussion to.
         """
         categories_map = {
diff --git a/src/discord_bot/cogs/rank.py b/src/discord_bot/cogs/rank.py
index 8a3a977..d233c28 100644
--- a/src/discord_bot/cogs/rank.py
+++ b/src/discord_bot/cogs/rank.py
@@ -1,7 +1,6 @@
 # standard imports
 import logging
 import os
-from typing import Union
 
 # lib imports
 import discord
@@ -397,7 +396,7 @@ def create_leaderboard_buttons(self, page, total_pages, platform):
     async def get_leaderboard_data(
             self,
             platform: str,
-            community_id: Union[int, str],
+            community_id: int | str,
             page: int = 1,
             per_page: int = 10,
     ):
diff --git a/src/discord_bot/cogs/support_commands.py b/src/discord_bot/cogs/support_commands.py
index 95e1188..8782902 100644
--- a/src/discord_bot/cogs/support_commands.py
+++ b/src/discord_bot/cogs/support_commands.py
@@ -139,11 +139,14 @@ async def project_command(ctx: discord.ApplicationContext, command: str):
 
     @staticmethod
     def render_command_file(command_file: str) -> str:
-        with open(command_file, "r", encoding='utf-8') as file:
-            with MarkdownRenderer(
-                    max_line_length=4096,  # this must be set to reflow the text
-                    normalize_whitespace=True) as renderer:
-                return renderer.render(mistletoe.Document(file))
+        with (
+            open(command_file, "r", encoding='utf-8') as file,
+            MarkdownRenderer(
+                max_line_length=4096,  # this must be set to reflow the text
+                normalize_whitespace=True,
+            ) as renderer,
+        ):
+            return renderer.render(mistletoe.Document(file))
 
     @discord.slash_command(
         name="docs",