diff --git a/backend/oasst_backend/prompt_repository.py b/backend/oasst_backend/prompt_repository.py
index 13c6cd23..0a6c193c 100644
--- a/backend/oasst_backend/prompt_repository.py
+++ b/backend/oasst_backend/prompt_repository.py
@@ -7,7 +7,14 @@ import oasst_backend.models.db_payload as db_payload
 from loguru import logger
 from oasst_backend.exceptions import OasstError, OasstErrorCode
 from oasst_backend.journal_writer import JournalWriter
-from oasst_backend.models import ApiClient, Person, Post, PostReaction, TextLabels, WorkPackage
+from oasst_backend.models import (
+    ApiClient,
+    Person,
+    Post,
+    PostReaction,
+    TextLabels,
+    WorkPackage,
+)
 from oasst_backend.models.payload_column_type import PayloadContainer
 from oasst_shared.schemas import protocol as protocol_schema
 from sqlmodel import Session, func
diff --git a/discord-bot/.env.example b/discord-bot/.env.example
index c518010d..7c414a53 100644
--- a/discord-bot/.env.example
+++ b/discord-bot/.env.example
@@ -1,4 +1,4 @@
 TOKEN=<discord bot token>
 DECLARE_GLOBAL_COMMANDS=<testing guild id>
 OWNER_IDS=<your user id>
-PREFIX="./"
\ No newline at end of file
+PREFIX="./"
diff --git a/discord-bot/.gitignore b/discord-bot/.gitignore
index 499012d2..ee1e23f2 100644
--- a/discord-bot/.gitignore
+++ b/discord-bot/.gitignore
@@ -7,4 +7,4 @@ __pycache__/
 .env
 
 # Database files
-*.db
\ No newline at end of file
+*.db
diff --git a/discord-bot/bot/__init__.py b/discord-bot/bot/__init__.py
index 3d04718d..66779a9c 100644
--- a/discord-bot/bot/__init__.py
+++ b/discord-bot/bot/__init__.py
@@ -1,2 +1,2 @@
-# -*- coding=utf-8 -*-
+# -*- coding: utf-8 -*-
 """The official Open-Assistant Discord Bot."""
diff --git a/discord-bot/bot/__main__.py b/discord-bot/bot/__main__.py
index f258d148..87032e40 100644
--- a/discord-bot/bot/__main__.py
+++ b/discord-bot/bot/__main__.py
@@ -1,4 +1,4 @@
-# -*- coding=utf-8 -*-
+# -*- coding: utf-8 -*-
 """Entry point for the bot."""
 import logging
 import os
diff --git a/discord-bot/bot/bot.py b/discord-bot/bot/bot.py
index 9b443986..1f801413 100644
--- a/discord-bot/bot/bot.py
+++ b/discord-bot/bot/bot.py
@@ -1,4 +1,4 @@
-# -*- coding=utf-8 -*-
+# -*- coding: utf-8 -*-
 """Bot logic."""
 import aiosqlite
 import hikari
@@ -26,7 +26,7 @@ async def on_starting(event: hikari.StartingEvent):
     miru.install(bot)  # component handler
     bot.load_extensions_from("./bot/extensions")  # load extensions
 
-    bot.d.db = await aiosqlite.connect("./bot/db/database.db")  # TODO: Update
+    bot.d.db = await aiosqlite.connect("./bot/db/database.db")
     await bot.d.db.executescript(open("./bot/db/schema.sql").read())
     await bot.d.db.commit()
 
diff --git a/discord-bot/bot/config.py b/discord-bot/bot/config.py
index e3addac9..fafcb308 100644
--- a/discord-bot/bot/config.py
+++ b/discord-bot/bot/config.py
@@ -1,11 +1,11 @@
-# -*- coding=utf-8 -*-
+# -*- coding: utf-8 -*-
 """Configuration for the bot."""
 
 import logging
 from dataclasses import dataclass
 from os import getenv
 
-from dotenv import load_dotenv
+from dotenv import load_dotenv  # type: ignore
 
 load_dotenv()
 
diff --git a/discord-bot/bot/db/schemas.py b/discord-bot/bot/db/schemas.py
index efb903b8..9c548e9f 100644
--- a/discord-bot/bot/db/schemas.py
+++ b/discord-bot/bot/db/schemas.py
@@ -1,9 +1,10 @@
 # -*- coding: utf-8 -*-
 """Database schemas."""
-from aiosqlite import Row, Connection
-from pydantic import BaseModel
 import typing as t
 
+from aiosqlite import Connection, Row
+from pydantic import BaseModel
+
 
 class GuildSettings(BaseModel):
     """Guild settings."""
diff --git a/discord-bot/bot/extensions/_example.py b/discord-bot/bot/extensions/_example.py
index 37783e43..76398881 100644
--- a/discord-bot/bot/extensions/_example.py
+++ b/discord-bot/bot/extensions/_example.py
@@ -1,3 +1,4 @@
+# -*- coding: utf-8 -*-
 # TODO: Convert file to markdown
 # -*- coding: utf-8 -*-
 """Example plugin for reference.
diff --git a/discord-bot/bot/extensions/text_labels.py b/discord-bot/bot/extensions/text_labels.py
index 325929d2..48e32763 100644
--- a/discord-bot/bot/extensions/text_labels.py
+++ b/discord-bot/bot/extensions/text_labels.py
@@ -8,13 +8,14 @@ import lightbulb
 import miru
 from aiosqlite import Connection
 
+from bot.db.schemas import GuildSettings
+from bot.utils import EMPTY
+
 plugin = lightbulb.Plugin(
     "TextLabels",
 )
 plugin.add_checks(lightbulb.guild_only)  # Context menus are only enabled in guilds
 
-from bot.utils import EMPTY
-from bot.db.schemas import GuildSettings
 
 DISCORD_GRAY = 0x2F3136
 
diff --git a/discord-bot/bot/extensions/work.py b/discord-bot/bot/extensions/work.py
index 1c1f38de..ecbe1710 100644
--- a/discord-bot/bot/extensions/work.py
+++ b/discord-bot/bot/extensions/work.py
@@ -4,18 +4,18 @@ import asyncio
 import logging
 import typing as t
 from datetime import datetime
-from aiosqlite import Connection
 
 import hikari
 import lightbulb
 import lightbulb.decorators
 import miru
+from aiosqlite import Connection
 from oasst_shared.schemas import protocol as protocol_schema
 from oasst_shared.schemas.protocol import TaskRequestType
 
 from bot.api_client import OasstApiClient, TaskType
-from bot.utils import EMPTY
 from bot.db.schemas import GuildSettings
+from bot.utils import EMPTY
 
 plugin = lightbulb.Plugin("WorkPlugin")
 
@@ -76,7 +76,7 @@ async def _handle_task(ctx: lightbulb.SlashContext, task_type: TaskRequestType)
                 )
             except asyncio.TimeoutError:
                 await ctx.author.send("Task timed out. Exiting")
-                # TODO: NACK task maybe?
+                await oasst_api.nack_task(task.id, reason="timed out")
                 return
 
             # Invalid response
diff --git a/discord-bot/dev-requirements.txt b/discord-bot/dev-requirements.txt
index 44a8d2cc..56393fdd 100644
--- a/discord-bot/dev-requirements.txt
+++ b/discord-bot/dev-requirements.txt
@@ -1,8 +1,8 @@
-nox
 
 black
-isort
 
 codespell
 flake8
-pyright
\ No newline at end of file
+isort
+nox
+pyright
diff --git a/discord-bot/flake8-requirements.txt b/discord-bot/flake8-requirements.txt
index 3509207e..a022d8c5 100644
--- a/discord-bot/flake8-requirements.txt
+++ b/discord-bot/flake8-requirements.txt
@@ -1,8 +1,4 @@
 flake8==6.0.0
-
-# Plugins
-
-Flake8-pyproject                 # use the pyproject.toml as the config file
 flake8-bandit                    # runs bandit
 flake8-black                     # runs black
 # flake8-broken-line               # forbey "\" linebreaks
@@ -21,6 +17,10 @@ flake8-mutable                   # mutable default argument detection
 flake8-pep3101                   # new-style format strings only
 flake8-print                     # complain about print statements in code
 flake8-printf-formatting         # forbey printf-style python2 string formatting
+
+# Plugins
+
+Flake8-pyproject                 # use the pyproject.toml as the config file
 flake8-pytest-style              # pytest checks
 flake8-raise                     # exception raising linting
 flake8-use-fstring                 # format string checking
diff --git a/discord-bot/message_templates.py b/discord-bot/message_templates.py
index dcb84c94..256f93d3 100644
--- a/discord-bot/message_templates.py
+++ b/discord-bot/message_templates.py
@@ -1,7 +1,8 @@
 # -*- coding: utf-8 -*-
 """Message templates for the discord bot."""
-import jinja2
 import typing
+
+import jinja2
 from loguru import logger
 
 
diff --git a/discord-bot/noxfile.py b/discord-bot/noxfile.py
index f85fc60c..891e87fb 100644
--- a/discord-bot/noxfile.py
+++ b/discord-bot/noxfile.py
@@ -1,4 +1,4 @@
-# -*- coding=utf-8 -*-
+# -*- coding: utf-8 -*-
 """Automated linting, formatting, and typechecking."""
 import nox
 from nox.sessions import Session
diff --git a/discord-bot/requirements.txt b/discord-bot/requirements.txt
index 17348c12..62b9b931 100644
--- a/discord-bot/requirements.txt
+++ b/discord-bot/requirements.txt
@@ -1,11 +1,11 @@
-hikari              # discord framework
-hikari[speedups]
-uvloop; os_name != 'nt'
-hikari-lightbulb    # command handler
-hikari-miru         # modals and buttons
-
-python-dotenv       # .env file support
-aiosqlite           # database
 aiohttp             # http client
 aiohttp[speedups]   # speedups for aiohttp
-loguru
\ No newline at end of file
+aiosqlite           # database
+hikari              # discord framework
+hikari-lightbulb    # command handler
+hikari-miru         # modals and buttons
+hikari[speedups]
+loguru
+
+python-dotenv       # .env file support
+uvloop; os_name != 'nt'