diff --git a/poetry.lock b/poetry.lock
index a4b306d01..45a0bec10 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -58,103 +58,103 @@ files = [
 
 [[package]]
 name = "aiohttp"
-version = "3.12.13"
+version = "3.12.14"
 description = "Async http client/server framework (asyncio)"
 optional = false
 python-versions = ">=3.9"
 groups = ["main"]
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 ]
 
 [package.dependencies]
 aiohappyeyeballs = ">=2.5.0"
-aiosignal = ">=1.1.2"
+aiosignal = ">=1.4.0"
 attrs = ">=17.3.0"
 frozenlist = ">=1.1.1"
 multidict = ">=4.5,<7.0"
@@ -166,14 +166,14 @@ speedups = ["Brotli ; platform_python_implementation == \"CPython\"", "aiodns (>
 
 [[package]]
 name = "aiosignal"
-version = "1.3.2"
+version = "1.4.0"
 description = "aiosignal: a list of registered asynchronous callbacks"
 optional = false
 python-versions = ">=3.9"
 groups = ["main"]
 files = [
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 ]
 
 [package.dependencies]
@@ -327,18 +327,19 @@ dev = ["backports.zoneinfo ; python_version < \"3.9\"", "freezegun (>=1.0,<2.0)"
 
 [[package]]
 name = "backrefs"
-version = "5.8"
+version = "5.9"
 description = "A wrapper around re and regex that adds additional back references."
 optional = false
 python-versions = ">=3.9"
 groups = ["docs"]
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 ssh = ["bcrypt (>=3.1.5)"]
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 test-randomorder = ["pytest-randomly"]
 
 [[package]]
@@ -939,14 +940,14 @@ voice = ["PyNaCl (>=1.3.0,<1.6)"]
 
 [[package]]
 name = "distlib"
-version = "0.3.9"
+version = "0.4.0"
 description = "Distribution utilities"
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 python-versions = "*"
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 [[package]]
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 [[package]]
 name = "htmlmin2"
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 [package.dependencies]
-more-itertools = "*"
+more_itertools = "*"
 
 [package.extras]
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+    {file = "xattr-1.2.0-pp39-pypy39_pp73-macosx_11_0_arm64.whl", hash = "sha256:5594fcbc38fdbb3af16a8ad18c37c81c8814955f0d636be857a67850cd556490"},
+    {file = "xattr-1.2.0-pp39-pypy39_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:017aac8005e1e84d5efa4b86c0896c6eb96f2331732d388600a5b999166fec1c"},
+    {file = "xattr-1.2.0-pp39-pypy39_pp73-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:2d27a64f695440450c119ae4bc8f54b0b726a812ebea1666fff3873236936f36"},
+    {file = "xattr-1.2.0-pp39-pypy39_pp73-manylinux_2_5_x86_64.manylinux1_x86_64.manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:1f7e7067e1a400ad4485536a9e84c3330373086b2324fafa26d07527eeb4b175"},
+    {file = "xattr-1.2.0.tar.gz", hash = "sha256:a64c8e21eff1be143accf80fd3b8fde3e28a478c37da298742af647ac3e5e0a7"},
 ]
 
 [package.dependencies]
diff --git a/tux/app.py b/tux/app.py
index 91eb4b4a0..4e8e0244c 100644
--- a/tux/app.py
+++ b/tux/app.py
@@ -1,17 +1,28 @@
-"""TuxApp: Orchestration and lifecycle management for the Tux Discord bot."""
+"""
+TuxApp: Main application entrypoint and lifecycle orchestrator.
+
+This module contains the `TuxApp` class, which serves as the primary entrypoint
+for the Tux Discord bot. It is responsible for:
+
+- **Environment Setup**: Validating configuration, initializing Sentry, and setting
+  up OS-level signal handlers for graceful shutdown.
+- **Bot Instantiation**: Creating the instance of the `Tux` bot class with the
+  appropriate intents, command prefix logic, and owner IDs.
+- **Lifecycle Management**: Starting the asyncio event loop and managing the
+  bot's main `start` and `shutdown` sequence, including handling `KeyboardInterrupt`.
+"""
 
 import asyncio
 import signal
-from types import FrameType
+import sys
 
 import discord
-import sentry_sdk
 from loguru import logger
 
 from tux.bot import Tux
 from tux.help import TuxHelp
 from tux.utils.config import CONFIG
-from tux.utils.env import get_current_env
+from tux.utils.sentry_manager import SentryManager
 
 
 async def get_prefix(bot: Tux, message: discord.Message) -> list[str]:
@@ -28,103 +39,69 @@ async def get_prefix(bot: Tux, message: discord.Message) -> list[str]:
 
 
 class TuxApp:
-    """Orchestrates the startup, shutdown, and environment for the Tux bot."""
+    """
+    Orchestrates the startup, shutdown, and environment for the Tux bot.
 
-    def __init__(self):
-        """Initialize the TuxApp with no bot instance yet."""
-        self.bot = None
+    This class is not a `discord.py` cog, but rather a top-level application
+    runner that manages the bot's entire lifecycle from an OS perspective.
+    """
 
-    def run(self) -> None:
-        """Run the Tux bot application (entrypoint for CLI)."""
-        asyncio.run(self.start())
+    # --- Initialization ---
 
-    def setup_sentry(self) -> None:
-        """Initialize Sentry for error monitoring and tracing."""
-        if not CONFIG.SENTRY_DSN:
-            logger.warning("No Sentry DSN configured, skipping Sentry setup")
-            return
-
-        logger.info("Setting up Sentry...")
-
-        try:
-            sentry_sdk.init(
-                dsn=CONFIG.SENTRY_DSN,
-                release=CONFIG.BOT_VERSION,
-                environment=get_current_env(),
-                enable_tracing=True,
-                attach_stacktrace=True,
-                send_default_pii=False,
-                traces_sample_rate=1.0,
-                profiles_sample_rate=1.0,
-                _experiments={
-                    "enable_logs": True,  # https://docs.sentry.io/platforms/python/logs/
-                },
-            )
+    def __init__(self):
+        """Initializes the TuxApp, setting the bot instance to None initially."""
+        self.bot: Tux | None = None
 
-            # Add additional global tags
-            sentry_sdk.set_tag("discord_library_version", discord.__version__)
+    # --- Application Lifecycle ---
 
-            logger.info(f"Sentry initialized: {sentry_sdk.is_initialized()}")
+    def run(self) -> None:
+        """
+        The main synchronous entrypoint for the application.
 
-        except Exception as e:
-            logger.error(f"Failed to initialize Sentry: {e}")
-
-    def setup_signals(self) -> None:
-        """Set up signal handlers for graceful shutdown."""
-        signal.signal(signal.SIGTERM, self.handle_sigterm)
-        signal.signal(signal.SIGINT, self.handle_sigterm)
-
-    def handle_sigterm(self, signum: int, frame: FrameType | None) -> None:
-        """Handle SIGTERM/SIGINT by raising KeyboardInterrupt for graceful shutdown."""
-        logger.info(f"Received signal {signum}")
-
-        if sentry_sdk.is_initialized():
-            with sentry_sdk.push_scope() as scope:
-                scope.set_tag("signal.number", signum)
-                scope.set_tag("lifecycle.event", "termination_signal")
-
-                sentry_sdk.add_breadcrumb(
-                    category="lifecycle",
-                    message=f"Received termination signal {signum}",
-                    level="info",
-                )
+        This method starts the asyncio event loop and runs the primary `start`
+        coroutine, effectively launching the bot.
+        """
+        asyncio.run(self.start())
 
-        raise KeyboardInterrupt
+    async def start(self) -> None:
+        """
+        The main asynchronous entrypoint for the application.
 
-    def validate_config(self) -> bool:
-        """Validate that all required configuration is present."""
-        if not CONFIG.BOT_TOKEN:
-            logger.critical("No bot token provided. Set DEV_BOT_TOKEN or PROD_BOT_TOKEN in your .env file.")
-            return False
+        This method orchestrates the entire bot startup sequence: setting up
+        Sentry and signal handlers, validating config, creating the `Tux`
+        instance, and connecting to Discord. It includes a robust
+        try/except/finally block to ensure graceful shutdown.
+        """
 
-        return True
+        # Initialize Sentry
+        SentryManager.setup()
 
-    async def start(self) -> None:
-        """Start the Tux bot, handling setup, errors, and shutdown."""
-        self.setup_sentry()
-
-        self.setup_signals()
+        # Set up signal handlers using the event loop for cross-platform compatibility
+        loop = asyncio.get_event_loop()
+        self.setup_signals(loop)
 
+        # Validate config
         if not self.validate_config():
             return
 
+        # Configure owner IDs, dynamically adding sysadmins if configured.
+        # This allows specified users to have access to sensitive commands like `eval`.
         owner_ids = {CONFIG.BOT_OWNER_ID}
-
         if CONFIG.ALLOW_SYSADMINS_EVAL:
             logger.warning(
-                "⚠️ Eval is enabled for sysadmins, this is potentially dangerous; see settings.yml.example for more info.",
+                "⚠️ Eval is enabled for sysadmins, this is potentially dangerous; "
+                "see settings.yml.example for more info.",
             )
             owner_ids.update(CONFIG.SYSADMIN_IDS)
-
         else:
             logger.warning("🔒️ Eval is disabled for sysadmins; see settings.yml.example for more info.")
 
+        # Instantiate the main bot class with all necessary parameters.
         self.bot = Tux(
             command_prefix=get_prefix,
             strip_after_prefix=True,
             case_insensitive=True,
             intents=discord.Intents.all(),
-            # owner_ids={CONFIG.BOT_OWNER_ID, *CONFIG.SYSADMIN_IDS},
             owner_ids=owner_ids,
             allowed_mentions=discord.AllowedMentions(everyone=False),
             help_command=TuxHelp(),
@@ -132,25 +109,75 @@ async def start(self) -> None:
             status=discord.Status.online,
         )
 
+        # Start the bot
         try:
+            # This is the main blocking call that connects to Discord and runs the bot.
             await self.bot.start(CONFIG.BOT_TOKEN, reconnect=True)
 
         except KeyboardInterrupt:
+            # This is caught when the user presses Ctrl+C.
             logger.info("Shutdown requested (KeyboardInterrupt)")
         except Exception as e:
-            logger.critical(f"Bot failed to start: {e}")
-            await self.shutdown()
-
+            # Catch any other unexpected exception during bot runtime.
+            logger.critical(f"Bot failed to start or run: {e}")
         finally:
+            # Ensure that shutdown is always called to clean up resources.
             await self.shutdown()
 
     async def shutdown(self) -> None:
-        """Gracefully shut down the bot and flush Sentry."""
+        """
+        Gracefully shuts down the bot and its resources.
+
+        This involves calling the bot's internal shutdown sequence and then
+        flushing any remaining Sentry events to ensure all data is sent.
+        """
         if self.bot and not self.bot.is_closed():
             await self.bot.shutdown()
 
-        if sentry_sdk.is_initialized():
-            sentry_sdk.flush()
-            await asyncio.sleep(0.1)
+        await SentryManager.flush_async()
+        await asyncio.sleep(0.1)  # Brief pause to allow buffers to flush
 
         logger.info("Shutdown complete")
+
+    # --- Environment Setup ---
+
+    def setup_signals(self, loop: asyncio.AbstractEventLoop) -> None:
+        """
+        Sets up OS-level signal handlers for graceful shutdown using the event loop for better cross-platform compatibility.
+
+        Note: loop.add_signal_handler may not be available on all platforms (e.g., Windows for some signals).
+        """
+
+        def handle_sigterm() -> None:
+            SentryManager.report_signal(signal.SIGTERM, None)
+
+        def handle_sigint() -> None:
+            SentryManager.report_signal(signal.SIGINT, None)
+
+        try:
+            loop.add_signal_handler(signal.SIGTERM, handle_sigterm)
+            loop.add_signal_handler(signal.SIGINT, handle_sigint)
+        except NotImplementedError:
+            # Fallback for platforms that do not support add_signal_handler (e.g., Windows)
+            signal.signal(signal.SIGINT, SentryManager.report_signal)
+            signal.signal(signal.SIGTERM, SentryManager.report_signal)
+            if sys.platform.startswith("win"):
+                # Document limitation
+                logger.warning(
+                    "Warning: Signal handling is limited on Windows. Some signals may not be handled as expected.",
+                )
+
+    def validate_config(self) -> bool:
+        """
+        Performs a pre-flight check for essential configuration.
+
+        Returns
+        -------
+        bool
+            True if the configuration is valid, False otherwise.
+        """
+        if not CONFIG.BOT_TOKEN:
+            logger.critical("No bot token provided. Set DEV_BOT_TOKEN or PROD_BOT_TOKEN in your .env file.")
+            return False
+
+        return True
diff --git a/tux/bot.py b/tux/bot.py
index 2e2f49491..c32d4f7ae 100644
--- a/tux/bot.py
+++ b/tux/bot.py
@@ -1,37 +1,78 @@
-"""Tux Discord bot core implementation.
-
-Defines the Tux bot class, which extends discord.py's Bot and manages
-setup, cog loading, error handling, and resource cleanup.
+"""
+Tux Discord bot core implementation.
+
+This module defines the primary `Tux` class, which serves as the central orchestrator
+for the entire bot application. It extends `discord.py`'s `commands.Bot` and is
+responsible for the following key areas:
+
+- **Lifecycle Management**: Handles the startup and shutdown sequences, ensuring
+  that all sub-systems are initialized and terminated gracefully.
+- **Component Orchestration**: Initializes and holds instances of various manager
+  classes (e.g., `TaskManager`, `SentryManager`, `EmojiManager`) that encapsulate
+  specific functionalities.
+- **Cog Loading**: Triggers the loading of all command cogs from the `tux/cogs`
+  directory via the `CogLoader`.
+- **Event Handling**: Implements core `discord.py` event listeners like `on_ready`
+  and `setup_hook` to manage the bot's state as it interacts with Discord.
 """
 
 from __future__ import annotations
 
 import asyncio
+import collections.abc
 import contextlib
 from collections.abc import Callable, Coroutine
+from dataclasses import dataclass
+from enum import Enum, auto
 from typing import Any
 
 import discord
-import sentry_sdk
 from discord.ext import commands, tasks
 from loguru import logger
 from rich.console import Console
 
-from tux.cog_loader import CogLoader
 from tux.database.client import db
+from tux.database.controllers import DatabaseController
 from tux.utils.banner import create_banner
-from tux.utils.config import Config
-from tux.utils.emoji import EmojiManager
+from tux.utils.config import CONFIG, Config
+from tux.utils.emoji_manager import EmojiManager
 from tux.utils.env import is_dev_mode
-from tux.utils.sentry import start_span, start_transaction
-
-# Create console for rich output
-console = Console(stderr=True, force_terminal=True)
+from tux.utils.sentry_manager import SentryManager
+from tux.utils.task_manager import TaskManager
+from tux.utils.tracing import (
+    instrument_bot_commands,
+    set_setup_phase_tag,
+    set_span_error,
+    start_span,
+    start_transaction,
+)
 
 # Type hint for discord.ext.tasks.Loop
 type TaskLoop = tasks.Loop[Callable[[], Coroutine[Any, Any, None]]]
 
 
+class TaskCategory(Enum):
+    """Categories for background tasks."""
+
+    SCHEDULED = auto()
+    GATEWAY = auto()
+    SYSTEM = auto()
+    COMMAND = auto()
+    UNKNOWN = auto()
+
+
+@dataclass
+class BotState:
+    """Manages the bot's operational state flags."""
+
+    is_shutting_down: bool = False
+    setup_complete: bool = False
+    start_time: float | None = None
+    emoji_manager_initialized: bool = False
+    hot_reload_loaded: bool = False
+    banner_logged: bool = False
+
+
 class DatabaseConnectionError(RuntimeError):
     """Raised when database connection fails."""
 
@@ -40,158 +81,179 @@ class DatabaseConnectionError(RuntimeError):
 
 class Tux(commands.Bot):
     """
-    Main bot class for Tux, extending discord.py's Bot.
+    The main class for the Tux Discord bot.
 
-    Handles setup, cog loading, error handling, Sentry tracing, and resource cleanup.
+    This class extends `discord.py`'s `commands.Bot` and serves as the central
+    orchestrator for the application. It is responsible for initializing
+    sub-systems (like database, Sentry, emoji management), loading cogs,
+    handling the bot's lifecycle (setup, shutdown), and processing events.
     """
 
+    # --- Initialization ---
+
     def __init__(self, *args: Any, **kwargs: Any) -> None:
-        """Initialize the Tux bot and start setup process."""
+        """
+        Initializes the Tux bot, its managers, and lifecycle steps.
+
+        This sets up the core state, managers (Sentry, Emoji, Task), and defines
+        the sequence of operations for the bot's startup and shutdown routines.
+        It also creates and schedules the main setup task.
+        """
         super().__init__(*args, **kwargs)
-        # Core state
-        self.is_shutting_down: bool = False
-        self.setup_complete: bool = False
-        self.start_time: float | None = None
-        self.setup_task: asyncio.Task[None] | None = None
-        self.active_sentry_transactions: dict[int, Any] = {}
 
-        self._emoji_manager_initialized = False
-        self._hot_reload_loaded = False
-        self._banner_logged = False
-        self._startup_task = None
+        # Core bot state flags, managed by the BotState dataclass.
+        self.state = BotState()
+        self.prefix_cache: dict[int, str] = {}
+        self.setup_task: asyncio.Task[None] | None = None
+        self._startup_task: asyncio.Task[None] | None = None
 
+        # Sub-systems and managers that encapsulate specific functionalities.
+        self.sentry_manager: SentryManager = SentryManager()
         self.emoji_manager = EmojiManager(self)
+        self.task_manager = TaskManager(self)
         self.console = Console(stderr=True, force_terminal=True)
 
+        # Bot lifecycle routines are now inlined directly in setup() and shutdown() methods
+        # for better readability and explicit sequencing
+
+        # The main setup routine is started as a background task immediately.
         logger.debug("Creating bot setup task")
         self.setup_task = asyncio.create_task(self.setup(), name="bot_setup")
         self.setup_task.add_done_callback(self._setup_callback)
 
+    # --- Setup & Lifecycle ---
+
     async def setup(self) -> None:
-        """Set up the bot: connect to database, load extensions, and start monitoring."""
+        """
+        Executes the bot's startup routine in a defined sequence.
+
+        This method performs each setup step in order to ensure the bot is properly
+        initialized before it goes online. If any step fails, the setup is aborted,
+        and a graceful shutdown is triggered.
+
+        Raises
+        ------
+        Exception
+            Propagates any exception that occurs during a setup step,
+            which is then caught, logged, and triggers a shutdown.
+        """
         try:
             with start_span("bot.setup", "Bot setup process") as span:
-                span.set_tag("setup_phase", "starting")
+                # Database connection
+                set_setup_phase_tag(span, "database", "starting")
                 await self._setup_database()
-                span.set_tag("setup_phase", "database_connected")
-                await self._load_extensions()
-                span.set_tag("setup_phase", "extensions_loaded")
-                await self._load_cogs()
-                span.set_tag("setup_phase", "cogs_loaded")
-                await self._setup_hot_reload()
-                span.set_tag("setup_phase", "hot_reload_ready")
-                self._start_monitoring()
-                span.set_tag("setup_phase", "monitoring_started")
+                set_setup_phase_tag(span, "database", "finished")
 
-        except Exception as e:
-            logger.critical(f"Critical error during setup: {e}")
+                # Load jishaku extension
+                set_setup_phase_tag(span, "jishaku", "starting")
+                await self._load_jishaku()
+                set_setup_phase_tag(span, "jishaku", "finished")
 
-            if sentry_sdk.is_initialized():
-                sentry_sdk.set_context("setup_failure", {"error": str(e), "error_type": type(e).__name__})
-                sentry_sdk.capture_exception(e)
+                # Load all cogs
+                set_setup_phase_tag(span, "cogs", "starting")
+                await self._load_cogs()
+                set_setup_phase_tag(span, "cogs", "finished")
 
-            await self.shutdown()
-            raise
+                # Setup hot reload
+                set_setup_phase_tag(span, "hot_reload", "starting")
+                await self._setup_hot_reload()
+                set_setup_phase_tag(span, "hot_reload", "finished")
 
-    async def _setup_database(self) -> None:
-        """Set up and validate the database connection."""
-        with start_span("bot.database_connect", "Setting up database connection") as span:
-            logger.info("Setting up database connection...")
+                # Register critical tasks
+                set_setup_phase_tag(span, "register_tasks", "starting")
+                await self._register_critical_tasks()
+                set_setup_phase_tag(span, "register_tasks", "finished")
 
-            try:
-                await db.connect()
-                self._validate_db_connection()
+                # Start monitoring
+                set_setup_phase_tag(span, "monitoring", "starting")
+                self.task_manager.start()
+                set_setup_phase_tag(span, "monitoring", "finished")
 
-                span.set_tag("db.connected", db.is_connected())
-                span.set_tag("db.registered", db.is_registered())
+                # Setup task instrumentation
+                set_setup_phase_tag(span, "instrument_tasks", "starting")
+                self.task_manager.setup_task_instrumentation()
+                set_setup_phase_tag(span, "instrument_tasks", "finished")
 
-                logger.info(f"Database connected: {db.is_connected()}")
-                logger.info(f"Database models registered: {db.is_registered()}")
+                # Setup command instrumentation
+                set_setup_phase_tag(span, "instrument_commands", "starting")
+                instrument_bot_commands(self)
+                set_setup_phase_tag(span, "instrument_commands", "finished")
 
-            except Exception as e:
-                span.set_status("internal_error")
-                span.set_data("error", str(e))
-                raise
+        except Exception as e:
+            # If any part of the setup fails, log the critical error
+            # and initiate a graceful shutdown to prevent a partial startup.
+            logger.critical(f"Critical error during setup: {e}")
 
-    async def _load_extensions(self) -> None:
-        """Load bot extensions and cogs, including Jishaku for debugging."""
-        with start_span("bot.load_jishaku", "Loading jishaku debug extension") as span:
-            try:
-                await self.load_extension("jishaku")
-                logger.info("Successfully loaded jishaku extension")
-                span.set_tag("jishaku.loaded", True)
+            self.sentry_manager.set_context("setup_failure", {"error": str(e), "error_type": type(e).__name__})
+            self.sentry_manager.capture_exception(e)
 
-            except commands.ExtensionError as e:
-                logger.warning(f"Failed to load jishaku: {e}")
-                span.set_tag("jishaku.loaded", False)
-                span.set_data("error", str(e))
+            await self.shutdown()
+            raise
 
-    def _start_monitoring(self) -> None:
-        """Start the background task monitoring loop."""
-        self._monitor_tasks_loop.start()
-        logger.debug("Task monitoring started")
+    async def shutdown(self) -> None:
+        """
+        Executes the bot's shutdown routine in a defined sequence.
+
+        This method ensures that all resources are cleaned up properly,
+        including cancelling tasks, stopping task loops, and closing
+        database and Discord connections. The `is_shutting_down` flag
+        prevents this from running more than once.
+        """
+        with start_transaction("bot.shutdown", "Bot shutdown process") as transaction:
+            # The is_shutting_down flag prevents re-entrant calls to shutdown.
+            if self.state.is_shutting_down:
+                logger.info("Shutdown already in progress. Exiting.")
+                transaction.set_data("already_shutting_down", True)
+                return
 
-    @staticmethod
-    def _validate_db_connection() -> None:
-        """Raise if the database is not connected or registered."""
-        if not db.is_connected() or not db.is_registered():
-            raise DatabaseConnectionError(DatabaseConnectionError.CONNECTION_FAILED)
+            self.state.is_shutting_down = True
+            transaction.set_tag("shutdown_initiated", True)
+            logger.info("Shutting down...")
 
-    def _setup_callback(self, task: asyncio.Task[None]) -> None:
-        """Handle setup task completion and update setup_complete flag."""
-        try:
-            task.result()
-            self.setup_complete = True
-            logger.info("Bot setup completed successfully")
+            # Handle setup task cleanup
+            transaction.set_tag("handle_setup_task_handled", False)
+            await self._handle_setup_task()
+            transaction.set_tag("handle_setup_task_handled", True)
 
-            if sentry_sdk.is_initialized():
-                sentry_sdk.set_tag("bot.setup_complete", True)
+            # Cancel all tasks
+            transaction.set_tag("cleanup_tasks_handled", False)
+            await self.task_manager.cancel_all_tasks()
+            transaction.set_tag("cleanup_tasks_handled", True)
 
-        except Exception as e:
-            logger.critical(f"Setup failed: {e}")
-            self.setup_complete = False
+            # Close connections
+            transaction.set_tag("close_connections_handled", False)
+            await self._close_connections()
+            transaction.set_tag("close_connections_handled", True)
 
-            if sentry_sdk.is_initialized():
-                sentry_sdk.set_tag("bot.setup_complete", False)
-                sentry_sdk.set_tag("bot.setup_failed", True)
-                sentry_sdk.capture_exception(e)
+            logger.info("Bot shutdown complete.")
+
+    # --- Event Handlers ---
 
     async def setup_hook(self) -> None:
-        """discord.py setup_hook: one-time async setup before connecting to Discord."""
-        if not self._emoji_manager_initialized:
+        """
+        Performs one-time async setup before connecting to Discord.
+
+        This `discord.py` hook is used to initialize the emoji manager and
+        schedule the `_post_ready_startup` task, which runs after both the
+        internal setup and the Discord connection are fully established.
+        """
+        # Initialize the emoji manager as soon as the bot's loop is running.
+        if not self.state.emoji_manager_initialized:
             await self.emoji_manager.init()
-            self._emoji_manager_initialized = True
+            self.state.emoji_manager_initialized = True
 
+        # The `_post_ready_startup` task should only be created once.
+        # This check prevents it from being recreated on subsequent reconnects.
         if self._startup_task is None or self._startup_task.done():
             self._startup_task = self.loop.create_task(self._post_ready_startup())
 
-    async def _post_ready_startup(self):
-        """Run after the bot is fully ready: log banner, set Sentry stats."""
-        await self.wait_until_ready()  # Wait for Discord connection and READY event
-
-        # Also wait for internal bot setup (cogs, db, etc.) to complete
-        await self._wait_for_setup()
-
-        if not self.start_time:
-            self.start_time = discord.utils.utcnow().timestamp()
-
-        if not self._banner_logged:
-            await self._log_startup_banner()
-            self._banner_logged = True
-
-        if sentry_sdk.is_initialized():
-            sentry_sdk.set_context(
-                "bot_stats",
-                {
-                    "guild_count": len(self.guilds),
-                    "user_count": len(self.users),
-                    "channel_count": sum(len(g.channels) for g in self.guilds),
-                    "uptime": discord.utils.utcnow().timestamp() - (self.start_time or 0),
-                },
-            )
-
     async def on_ready(self) -> None:
-        """Handle bot ready event."""
+        """
+        Called when the bot is ready and connected to Discord.
+
+        This sets the bot's presence and indicates that it is online.
+        It waits for the internal setup to complete before proceeding.
+        """
         await self._wait_for_setup()
 
         # Set bot status
@@ -199,156 +261,196 @@ async def on_ready(self) -> None:
         await self.change_presence(activity=activity, status=discord.Status.online)
 
     async def on_disconnect(self) -> None:
-        """Log and report when the bot disconnects from Discord."""
-        logger.warning("Bot has disconnected from Discord.")
-
-        if sentry_sdk.is_initialized():
-            with sentry_sdk.push_scope() as scope:
-                scope.set_tag("event_type", "disconnect")
-                scope.set_level("info")
-                sentry_sdk.capture_message(
-                    "Bot disconnected from Discord, this happens sometimes and is fine as long as it's not happening too often",
-                )
-
-    # --- Sentry Transaction Tracking ---
-
-    def start_interaction_transaction(self, interaction_id: int, name: str) -> Any:
-        """Start a Sentry transaction for a slash command interaction."""
-        if not sentry_sdk.is_initialized():
-            return None
-
-        transaction = sentry_sdk.start_transaction(
-            op="slash_command",
-            name=f"Slash Command: {name}",
-            description=f"Processing slash command {name}",
-        )
+        """
+        Logs and reports when the bot disconnects from Discord.
 
-        transaction.set_tag("interaction.id", interaction_id)
-        transaction.set_tag("command.name", name)
-        transaction.set_tag("command.type", "slash")
+        This is a normal event during bot operation and is usually followed
+        by a reconnect, so it is logged as a warning.
+        """
+        logger.info("Bot has disconnected from Discord.")
 
-        self.active_sentry_transactions[interaction_id] = transaction
+        self.sentry_manager.capture_message(
+            "Bot disconnected from Discord, this happens sometimes and is fine as long as it's not happening too often",
+        )
 
-        return transaction
+    # --- Internal Setup & Shutdown Steps ---
 
-    def start_command_transaction(self, message_id: int, name: str) -> Any:
-        """Start a Sentry transaction for a prefix command."""
-        if not sentry_sdk.is_initialized():
-            return None
+    async def _setup_database(self) -> None:
+        """
+        Connects to the database and validates the connection.
+
+        Raises
+        ------
+        Exception
+            Propagates any database connection errors from the client.
+        """
+        with start_span("bot.database_connect", "Setting up database connection") as span:
+            logger.info("Setting up database connection...")
 
-        transaction = sentry_sdk.start_transaction(
-            op="prefix_command",
-            name=f"Prefix Command: {name}",
-            description=f"Processing prefix command {name}",
-        )
+            try:
+                await db.connect()
+                self._validate_db_connection()
 
-        transaction.set_tag("message.id", message_id)
-        transaction.set_tag("command.name", name)
-        transaction.set_tag("command.type", "prefix")
+                span.set_tag("db.connected", db.is_connected())
+                span.set_tag("db.registered", db.is_registered())
 
-        self.active_sentry_transactions[message_id] = transaction
+                logger.info(f"Database connected: {db.is_connected()}")
+                logger.info(f"Database models registered: {db.is_registered()}")
 
-        return transaction
+            except Exception as e:
+                set_span_error(span, e, "db_error")
+                raise
 
-    def finish_transaction(self, transaction_id: int, status: str = "ok") -> None:
-        """Finish a stored Sentry transaction with the given status."""
-        if not sentry_sdk.is_initialized():
-            return
+    async def _load_jishaku(self) -> None:
+        """Loads the Jishaku extension for debugging and development."""
+        with start_span("bot.load_jishaku", "Loading jishaku debug extension") as span:
+            try:
+                await self.load_extension("jishaku")
+                logger.info("Successfully loaded jishaku extension")
+                span.set_tag("jishaku.loaded", True)
 
-        if transaction := self.active_sentry_transactions.pop(transaction_id, None):
-            transaction.set_status(status)
-            transaction.finish()
+            except commands.ExtensionError as e:
+                logger.warning(f"Failed to load jishaku: {e}")
+                span.set_tag("jishaku.loaded", False)
+                span.set_data("error", str(e))
 
-    async def _wait_for_setup(self) -> None:
-        """Wait for setup to complete if not already done."""
-        if self.setup_task and not self.setup_task.done():
-            with start_span("bot.wait_setup", "Waiting for setup to complete"):
-                try:
-                    await self.setup_task
+    async def _load_cogs(self) -> None:
+        """
+        Loads all command cogs using the CogLoader utility.
 
-                except Exception as e:
-                    logger.critical(f"Setup failed during on_ready: {e}")
-                    if sentry_sdk.is_initialized():
-                        sentry_sdk.capture_exception(e)
+        Raises
+        ------
+        Exception
+            Propagates any exceptions that occur during cog loading.
+        """
+        from tux.cog_loader import CogLoader  # noqa: PLC0415
 
-                    await self.shutdown()
+        with start_span("bot.load_cogs", "Loading all cogs") as span:
+            logger.info("Loading cogs...")
 
-    @tasks.loop(seconds=60)
-    async def _monitor_tasks_loop(self) -> None:
-        """Monitor and clean up running tasks every 60 seconds."""
-        with start_span("bot.monitor_tasks", "Monitoring async tasks"):
             try:
-                all_tasks = [t for t in asyncio.all_tasks() if t is not asyncio.current_task()]
-                tasks_by_type = self._categorize_tasks(all_tasks)
-                await self._process_finished_tasks(tasks_by_type)
+                await CogLoader.setup(self)
+                span.set_tag("cogs_loaded", True)
 
             except Exception as e:
-                logger.error(f"Task monitoring failed: {e}")
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
-
-                msg = "Critical failure in task monitoring system"
-                raise RuntimeError(msg) from e
-
-    def _categorize_tasks(self, tasks: list[asyncio.Task[Any]]) -> dict[str, list[asyncio.Task[Any]]]:
-        """Categorize tasks by their type for monitoring/cleanup."""
-        tasks_by_type: dict[str, list[asyncio.Task[Any]]] = {
-            "SCHEDULED": [],
-            "GATEWAY": [],
-            "SYSTEM": [],
-            "COMMAND": [],
-        }
-
-        for task in tasks:
-            if task.done():
-                continue
-
-            name = task.get_name()
-
-            if name.startswith("discord-ext-tasks:"):
-                tasks_by_type["SCHEDULED"].append(task)
-            elif name.startswith(("discord.py:", "discord-voice-", "discord-gateway-")):
-                tasks_by_type["GATEWAY"].append(task)
-            elif "command_" in name.lower():
-                tasks_by_type["COMMAND"].append(task)
-            else:
-                tasks_by_type["SYSTEM"].append(task)
-
-        return tasks_by_type
-
-    async def _process_finished_tasks(self, tasks_by_type: dict[str, list[asyncio.Task[Any]]]) -> None:
-        """Process and clean up finished tasks."""
-        for task_list in tasks_by_type.values():
-            for task in task_list:
-                if task.done():
-                    with contextlib.suppress(asyncio.CancelledError):
-                        await task
+                logger.critical(f"Error loading cogs: {e}")
+                span.set_tag("cogs_loaded", False)
+                set_span_error(span, e, "error")
+                self.sentry_manager.capture_exception(e)
+                raise
 
-    async def shutdown(self) -> None:
-        """Gracefully shut down the bot and clean up resources."""
-        with start_transaction("bot.shutdown", "Bot shutdown process") as transaction:
-            if self.is_shutting_down:
-                logger.info("Shutdown already in progress. Exiting.")
-                transaction.set_data("already_shutting_down", True)
-                return
+    async def _setup_hot_reload(self) -> None:
+        """
+        Sets up the hot-reload system for development.
+
+        This allows for automatic reloading of cogs and modules when files
+        are changed, speeding up the development workflow.
+
+        Raises
+        ------
+        Exception
+            Propagates exceptions from `load_extension` if hot-reload fails.
+        """
+        if not self.state.hot_reload_loaded and "tux.utils.hot_reload" not in self.extensions:
+            with start_span("bot.setup_hot_reload", "Setting up hot reload system"):
+                try:
+                    await self.load_extension("tux.utils.hot_reload")
+                    self.state.hot_reload_loaded = True
+                    logger.info("🔥 Hot reload system initialized")
+                except Exception as e:
+                    logger.error(f"Failed to load hot reload extension: {e}")
+                    self.sentry_manager.capture_exception(e)
 
-            self.is_shutting_down = True
-            transaction.set_tag("shutdown_initiated", True)
-            logger.info("Shutting down...")
+    async def _register_critical_tasks(self) -> None:
+        """
+        Registers critical tasks after cogs are loaded.
 
-            await self._handle_setup_task()
-            transaction.set_tag("setup_task_handled", True)
+        This method uses dynamic discovery to find critical tasks from cogs,
+        making the system more flexible and cog-driven.
+        """
+        with start_span("bot.register_critical_tasks", "Registering critical tasks") as span:
+            logger.info("Registering critical tasks...")
 
-            await self._cleanup_tasks()
-            transaction.set_tag("tasks_cleaned", True)
+            try:
+                # Clear any existing critical tasks to avoid duplicates
+                self.task_manager.critical_tasks.clear()
+                self.task_manager.task_metrics.clear()
 
-            await self._close_connections()
-            transaction.set_tag("connections_closed", True)
+                # Discover and register tasks from cogs dynamically
+                self.task_manager.discover_and_register_cog_tasks()
 
-            logger.info("Bot shutdown complete.")
+                span.set_tag("tasks_registered", len(self.task_manager.critical_tasks))
+                logger.info(f"Registered {len(self.task_manager.critical_tasks)} critical tasks.")
+
+            except Exception as e:
+                logger.critical(f"Failed to register critical tasks: {e}")
+                self.sentry_manager.capture_exception(e)
+                raise
+
+    def _handle_cog_unload(self, cog_name: str) -> None:
+        """
+        Handle cleanup when a cog is unloaded.
+
+        This method cleans up any critical tasks associated with the unloaded cog
+        to prevent orphaned task references.
+
+        Parameters
+        ----------
+        cog_name : str
+            The name of the cog that was unloaded.
+        """
+        logger.debug(f"Handling unload for cog: {cog_name}")
+        self.task_manager.cleanup_cog_tasks(cog_name)
+
+    async def remove_cog(
+        self,
+        name: str,
+        /,
+        *,
+        guild: discord.abc.Snowflake | None = None,
+        guilds: collections.abc.Sequence[discord.abc.Snowflake] | None = None,
+    ) -> commands.Cog | None:
+        """
+        Remove a cog and clean up associated tasks.
+
+        This overrides the default remove_cog method to ensure that critical tasks
+        associated with the unloaded cog are properly cleaned up when the cog is unloaded.
+
+        Parameters
+        ----------
+        name : str
+            The name of the cog to remove.
+        guild : discord.abc.Snowflake | None, optional
+            The guild to remove the cog from, by default None
+        guilds : collections.abc.Sequence[discord.abc.Snowflake] | None, optional
+            The guilds to remove the cog from, by default None
+
+        Returns
+        -------
+        commands.Cog | None
+            The removed cog, or None if it wasn't loaded.
+        """
+        # Remove the cog using the parent method
+        if guilds is not None:
+            removed_cog = await super().remove_cog(name, guild=guild, guilds=guilds)
+        elif guild is not None:
+            removed_cog = await super().remove_cog(name, guild=guild)
+        else:
+            removed_cog = await super().remove_cog(name)
+
+        # Clean up associated tasks if the cog was successfully removed
+        if removed_cog is not None:
+            self._handle_cog_unload(name)
+
+        return removed_cog
 
     async def _handle_setup_task(self) -> None:
-        """Handle setup task during shutdown."""
+        """
+        Handles the main setup task during shutdown.
+
+        If the bot is shut down while the initial setup is still running,
+        this method ensures the setup task is properly cancelled.
+        """
         with start_span("bot.handle_setup_task", "Handling setup task during shutdown"):
             if self.setup_task and not self.setup_task.done():
                 self.setup_task.cancel()
@@ -356,132 +458,126 @@ async def _handle_setup_task(self) -> None:
                 with contextlib.suppress(asyncio.CancelledError):
                     await self.setup_task
 
-    async def _cleanup_tasks(self) -> None:
-        """Clean up all running tasks."""
-        with start_span("bot.cleanup_tasks", "Cleaning up running tasks"):
+    async def _close_connections(self) -> None:
+        """Closes Discord and database connections."""
+        with start_span("bot.close_connections", "Closing connections"):
+            await self._close_discord()
+            await self._close_database()
+
+    async def _close_discord(self) -> None:
+        """Closes the connection to the Discord Gateway."""
+        with start_span("bot.close_discord", "Closing Discord connection") as span:
             try:
-                await self._stop_task_loops()
-
-                all_tasks = [t for t in asyncio.all_tasks() if t is not asyncio.current_task()]
-                tasks_by_type = self._categorize_tasks(all_tasks)
-
-                await self._cancel_tasks(tasks_by_type)
-
+                logger.debug("Closing Discord connection.")
+                await self.close()
+                logger.debug("Discord connection closed.")
+                span.set_tag("discord_closed", True)
             except Exception as e:
-                logger.error(f"Error during task cleanup: {e}")
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
-
-    async def _stop_task_loops(self) -> None:
-        """Stop all task loops in cogs."""
-        with start_span("bot.stop_task_loops", "Stopping task loops"):
-            for cog_name in self.cogs:
-                cog = self.get_cog(cog_name)
-                if not cog:
-                    continue
-
-                for name, value in cog.__dict__.items():
-                    if isinstance(value, tasks.Loop):
-                        try:
-                            value.stop()
-                            logger.debug(f"Stopped task loop {cog_name}.{name}")
-
-                        except Exception as e:
-                            logger.error(f"Error stopping task loop {cog_name}.{name}: {e}")
-
-            if hasattr(self, "_monitor_tasks_loop") and self._monitor_tasks_loop.is_running():
-                self._monitor_tasks_loop.stop()
-
-    async def _cancel_tasks(self, tasks_by_type: dict[str, list[asyncio.Task[Any]]]) -> None:
-        """Cancel tasks by category."""
-        with start_span("bot.cancel_tasks", "Cancelling tasks by category") as span:
-            for task_type, task_list in tasks_by_type.items():
-                if not task_list:
-                    continue
-
-                task_names: list[str] = []
-
-                for t in task_list:
-                    name = t.get_name() or "unnamed"
-                    if name in ("None", "unnamed"):
-                        coro = t.get_coro()
-                        name = getattr(coro, "__qualname__", str(coro))
-                    task_names.append(name)
-                names = ", ".join(task_names)
-
-                logger.debug(f"Cancelling {len(task_list)} {task_type}: {names}")
-                span.set_data(f"tasks.{task_type.lower()}", task_names)
-
-                for task in task_list:
-                    task.cancel()
+                logger.error(f"Error during Discord shutdown: {e}")
+                span.set_tag("discord_closed", False)
+                set_span_error(span, e, "discord_error")
+                self.sentry_manager.capture_exception(e)
+
+    async def _close_database(self) -> None:
+        """Closes the database connection pool."""
+        with start_span("bot.close_database", "Closing database connection") as span:
+            if not db.is_connected():
+                logger.warning("Database was not connected, no disconnect needed.")
+                span.set_tag("db_connected", False)
+                return
 
-                results = await asyncio.gather(*task_list, return_exceptions=True)
+            try:
+                logger.debug("Closing database connection.")
+                await db.disconnect()
+                logger.debug("Database connection closed.")
+                span.set_tag("db_closed", True)
+            except Exception as e:
+                logger.critical(f"Error during database disconnection: {e}")
+                span.set_tag("db_closed", False)
+                set_span_error(span, e, "db_error")
+                self.sentry_manager.capture_exception(e)
 
-                for result in results:
-                    if isinstance(result, Exception) and not isinstance(result, asyncio.CancelledError):
-                        logger.error(f"Exception during task cancellation for {task_type}: {result!r}")
+    # --- Internal Helpers ---
 
-                logger.debug(f"Cancelled {task_type}")
+    def _setup_callback(self, task: asyncio.Task[None]) -> None:
+        """
+        A callback that runs upon completion of the main setup task.
 
-    async def _close_connections(self) -> None:
-        """Close Discord and database connections."""
-        with start_span("bot.close_connections", "Closing connections") as span:
-            try:
-                logger.debug("Closing Discord connections.")
+        This updates the bot's state to reflect whether the setup
+        was successful or failed.
 
-                await self.close()
-                logger.debug("Discord connections closed.")
-                span.set_tag("discord_closed", True)
+        Parameters
+        ----------
+        task : asyncio.Task[None]
+            The setup task that has completed.
+        """
+        try:
+            task.result()
+            self.state.setup_complete = True
+            logger.info("Bot setup completed successfully")
+            self.sentry_manager.set_tag("bot.setup_complete", True)
 
-            except Exception as e:
-                logger.error(f"Error during Discord shutdown: {e}")
+        except Exception as e:
+            logger.critical(f"Setup failed: {e}")
+            self.state.setup_complete = False
 
-                span.set_tag("discord_closed", False)
-                span.set_data("discord_error", str(e))
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
+            self.sentry_manager.set_tag("bot.setup_complete", False)
+            self.sentry_manager.set_tag("bot.setup_failed", True)
+            self.sentry_manager.capture_exception(e)
 
-            try:
-                logger.debug("Closing database connections.")
+    async def _wait_for_setup(self) -> None:
+        """
+        Waits for the internal setup task to complete before proceeding.
 
-                if db.is_connected():
-                    await db.disconnect()
+        This is a crucial step in event handlers like `on_ready` to ensure
+        that cogs, database connections, etc., are available before the bot
+        tries to interact with them.
+        """
+        if self.setup_task and not self.setup_task.done():
+            with start_span("bot.wait_setup", "Waiting for setup to complete"):
+                try:
+                    await self.setup_task
 
-                    logger.debug("Database connections closed.")
-                    span.set_tag("db_closed", True)
+                except Exception as e:
+                    logger.critical(f"Setup failed during on_ready: {e}")
+                    self.sentry_manager.capture_exception(e)
 
-                else:
-                    logger.warning("Database was not connected, no disconnect needed.")
-                    span.set_tag("db_connected", False)
+                    await self.shutdown()
 
-            except Exception as e:
-                logger.critical(f"Error during database disconnection: {e}")
-                span.set_tag("db_closed", False)
-                span.set_data("db_error", str(e))
+    async def _post_ready_startup(self):
+        """
+        Runs tasks that require the bot to be fully online and ready.
 
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
+        This method waits for two conditions:
+        1. The bot is connected to the Discord Gateway (`wait_until_ready`).
+        2. The bot has completed its own internal setup (`_wait_for_setup`).
 
-    async def _load_cogs(self) -> None:
-        """Load bot cogs using CogLoader."""
-        with start_span("bot.load_cogs", "Loading all cogs") as span:
-            logger.info("Loading cogs...")
+        Once ready, it logs the startup banner and reports initial stats.
+        """
+        await self.wait_until_ready()
 
-            try:
-                await CogLoader.setup(self)
-                span.set_tag("cogs_loaded", True)
+        # Also wait for internal bot setup (cogs, db, etc.) to complete
+        await self._wait_for_setup()
 
-            except Exception as e:
-                logger.critical(f"Error loading cogs: {e}")
-                span.set_tag("cogs_loaded", False)
-                span.set_data("error", str(e))
+        if not self.state.start_time:
+            self.state.start_time = discord.utils.utcnow().timestamp()
 
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
-                raise
+        if not self.state.banner_logged:
+            await self._log_startup_banner()
+            self.state.banner_logged = True
+
+        self.sentry_manager.set_context(
+            "bot_stats",
+            {
+                "guild_count": len(self.guilds),
+                "user_count": len(self.users),
+                "channel_count": sum(len(g.channels) for g in self.guilds),
+                "uptime": discord.utils.utcnow().timestamp() - (self.state.start_time or 0),
+            },
+        )
 
     async def _log_startup_banner(self) -> None:
-        """Log bot startup information (banner, stats, etc.)."""
+        """Logs the bot's startup banner and stats to the console."""
         with start_span("bot.log_banner", "Displaying startup banner"):
             banner = create_banner(
                 bot_name=Config.BOT_NAME,
@@ -493,17 +589,86 @@ async def _log_startup_banner(self) -> None:
                 dev_mode=is_dev_mode(),
             )
 
-            console.print(banner)
+            self.console.print(banner)
 
-    async def _setup_hot_reload(self) -> None:
-        """Set up hot reload system after all cogs are loaded."""
-        if not self._hot_reload_loaded and "tux.utils.hot_reload" not in self.extensions:
-            with start_span("bot.setup_hot_reload", "Setting up hot reload system"):
-                try:
-                    await self.load_extension("tux.utils.hot_reload")
-                    self._hot_reload_loaded = True
-                    logger.info("🔥 Hot reload system initialized")
-                except Exception as e:
-                    logger.error(f"Failed to load hot reload extension: {e}")
-                    if sentry_sdk.is_initialized():
-                        sentry_sdk.capture_exception(e)
+    @staticmethod
+    def _validate_db_connection() -> None:
+        """
+        Ensures the database is properly connected.
+
+        Raises
+        ------
+        DatabaseConnectionError
+            If the database is not connected or models are not registered.
+        """
+        if not db.is_connected() or not db.is_registered():
+            raise DatabaseConnectionError(DatabaseConnectionError.CONNECTION_FAILED)
+
+    async def _get_prefix(self, bot: Tux, message: discord.Message) -> list[str]:
+        """
+        Resolves the command prefix for a given message with caching.
+
+        This method dynamically retrieves the command prefix for a guild, caching
+        the result to avoid repeated database lookups. It falls back to the
+        default prefix if one is not configured or if a database error occurs.
+        It also allows the bot to be invoked by mentioning it.
+
+        Parameters
+        ----------
+        bot : Tux
+            The instance of the bot.
+        message : discord.Message
+            The message to resolve the prefix for.
+
+        Returns
+        -------
+        list[str]
+            A list of command prefixes, including mentions.
+        """
+        if not message.guild:
+            return commands.when_mentioned_or(CONFIG.DEFAULT_PREFIX)(self, message)
+
+        # Check the cache for a stored prefix
+        if cached_prefix := self.prefix_cache.get(message.guild.id):
+            return commands.when_mentioned_or(cached_prefix)(self, message)
+
+        # If not in cache, query the database
+        if db.is_connected():
+            try:
+                if prefix := await DatabaseController().guild_config.get_guild_prefix(message.guild.id):
+                    self.prefix_cache[message.guild.id] = prefix
+                    return commands.when_mentioned_or(prefix)(self, message)
+            except Exception as e:
+                logger.error(f"Error getting guild prefix for guild {message.guild.id}: {e}")
+                self.sentry_manager.capture_exception(e)
+
+        # Fallback to the default prefix if no custom one is found
+        return commands.when_mentioned_or(CONFIG.DEFAULT_PREFIX)(self, message)
+
+    async def invoke(self, ctx: commands.Context[Any]) -> None:
+        """
+        Overrides the default invoke method to wrap command execution in a Sentry transaction.
+
+        This ensures that every command invocation is traced, allowing for performance
+        monitoring and capturing of related spans (e.g., database queries).
+
+        Parameters
+        ----------
+        ctx : commands.Context[Any]
+            The context of the command invocation.
+        """
+        if not self.sentry_manager.is_initialized:
+            await super().invoke(ctx)
+            return
+
+        # Create a transaction for every invocation, even if ctx.command is None
+        command_name = getattr(ctx.command, "qualified_name", None) or "unknown_command"
+        op = "command"
+        description = ctx.message.content
+
+        with start_transaction(op, command_name, description):
+            # Set comprehensive context using the SentryManager
+            self.sentry_manager.set_command_context(ctx)
+
+            # Execute the original command invocation logic
+            await super().invoke(ctx)
diff --git a/tux/cli/__init__.py b/tux/cli/__init__.py
old mode 100644
new mode 100755
diff --git a/tux/cli/core.py b/tux/cli/core.py
old mode 100644
new mode 100755
diff --git a/tux/cli/database.py b/tux/cli/database.py
old mode 100644
new mode 100755
diff --git a/tux/cli/dev.py b/tux/cli/dev.py
old mode 100644
new mode 100755
index 96ad5a46d..4296ef6b9
--- a/tux/cli/dev.py
+++ b/tux/cli/dev.py
@@ -38,3 +38,15 @@ def type_check() -> int:
 def check() -> int:
     """Run pre-commit checks."""
     return run_command(["pre-commit", "run", "--all-files"])
+
+
+@command_registration_decorator(dev_group, name="check-all")
+def check_all() -> int:
+    """Run all development checks (pre-commit + type checking)."""
+    # Run pre-commit first
+    pre_commit_result = run_command(["pre-commit", "run", "--all-files"])
+    if pre_commit_result != 0:
+        return pre_commit_result
+
+    # Then run type checking
+    return run_command(["pyright"])
diff --git a/tux/cli/docker.py b/tux/cli/docker.py
old mode 100644
new mode 100755
diff --git a/tux/cli/docs.py b/tux/cli/docs.py
old mode 100644
new mode 100755
diff --git a/tux/cli/test.py b/tux/cli/test.py
old mode 100644
new mode 100755
diff --git a/tux/cli/ui.py b/tux/cli/ui.py
old mode 100644
new mode 100755
diff --git a/tux/cog_loader.py b/tux/cog_loader.py
index b54e4195d..7cacf5c60 100644
--- a/tux/cog_loader.py
+++ b/tux/cog_loader.py
@@ -1,39 +1,91 @@
-import asyncio
+"""
+CogLoader: A robust cog loader for the Tux bot.
+
+This module provides the `CogLoader` class, which is responsible for discovering,
+loading, and managing all cogs (Discord.py extensions) for the bot. It includes
+features for priority-based loading, performance tracking, and detailed error
+reporting with Sentry integration.
+"""
+
+from __future__ import annotations
+
 import time
-import traceback
 from collections import defaultdict
-from collections.abc import Sequence
+from itertools import groupby
 from pathlib import Path
 
-import aiofiles
-import aiofiles.os
-import sentry_sdk
 from discord.ext import commands
 from loguru import logger
 
 from tux.utils.config import CONFIG
-from tux.utils.sentry import safe_set_name, span, start_span, transaction
+from tux.utils.tracing import (
+    capture_span_exception,
+    enhanced_span,
+    set_span_attributes,
+    span,
+    transaction,
+)
 
 
 class CogLoadError(Exception):
     """Raised when a cog fails to load."""
 
-    FAILED_TO_LOAD = "Failed to load cogs"
-    FAILED_TO_LOAD_FOLDER = "Failed to load cogs from folder"
-    FAILED_TO_INITIALIZE = "Failed to initialize cog loader"
 
-    def __init__(self, message: str) -> None:
-        self.message = message
-        super().__init__(self.message)
+class CogLoadResult:
+    """
+    Encapsulates the result of a cog loading operation.
+
+    Attributes
+    ----------
+    module : str
+        The full import path of the cog.
+    success : bool
+        Whether the cog loaded successfully.
+    load_time : float
+        The time taken to load the cog, in seconds.
+    error : Exception | None
+        The exception raised during loading, if any.
+    """
+
+    def __init__(self, module: str, success: bool, load_time: float, error: Exception | None = None) -> None:
+        self.module = module
+        self.success = success
+        self.load_time = load_time
+        self.error = error
+
+    @property
+    def load_time_ms(self) -> float:
+        """
+        Return the cog load time in milliseconds.
+
+        Returns
+        -------
+        float
+            The load time in milliseconds.
+        """
+        return self.load_time * 1000
 
 
 class CogLoader(commands.Cog):
+    """
+    A robust cog loader with priority-based loading, performance tracking,
+    and detailed Sentry integration.
+    """
+
+    # --- Initialization ---
+
     def __init__(self, bot: commands.Bot) -> None:
+        """
+        Initializes the CogLoader.
+
+        Parameters
+        ----------
+        bot : commands.Bot
+            The bot instance.
+        """
         self.bot = bot
-        self.cog_ignore_list: set[str] = CONFIG.COG_IGNORE_LIST
-        # Track load times for performance monitoring
+        self.cog_ignore_list: set[str] = set(CONFIG.COG_IGNORE_LIST)
         self.load_times: defaultdict[str, float] = defaultdict(float)
-        # Define load order priorities (higher number = higher priority)
         self.load_priorities = {
             "services": 90,
             "admin": 80,
@@ -47,9 +99,31 @@ def __init__(self, bot: commands.Bot) -> None:
             "tools": 5,
         }
 
-    async def is_cog_eligible(self, filepath: Path) -> bool:
+    # --- Cog Discovery & Metadata ---
+
+    @staticmethod
+    def _path_to_module(path: Path) -> str:
         """
-        Checks if the specified file is an eligible cog.
+        Converts a Path object to a Python module path.
+
+        Example:
+            tux/cogs/admin.py -> tux.cogs.admin
+
+        Parameters
+        ----------
+        path : Path
+            The file path to convert.
+
+        Returns
+        -------
+        str
+            The Python module import path.
+        """
+        return ".".join(path.parts).removesuffix(".py")
+
+    def _is_eligible_cog_file(self, filepath: Path) -> bool:
+        """
+        Checks if a file is an eligible cog for loading.
 
         Parameters
         ----------
@@ -61,316 +135,378 @@ async def is_cog_eligible(self, filepath: Path) -> bool:
         bool
             True if the file is an eligible cog, False otherwise.
         """
-        cog_name: str = filepath.stem
+        if filepath.suffix != ".py" or not filepath.is_file() or filepath.stem.startswith("_"):
+            return False
 
+        cog_name = filepath.stem
         if cog_name in self.cog_ignore_list:
-            logger.warning(f"Skipping {cog_name} as it is in the ignore list.")
+            logger.trace(f"Skipping {cog_name} as it is in the ignore list.")
             return False
 
-        return filepath.suffix == ".py" and not cog_name.startswith("_") and await aiofiles.os.path.isfile(filepath)
+        return True
 
-    @span("cog.load_single")
-    async def _load_single_cog(self, path: Path) -> None:
+    def _get_cog_priority(self, path: Path) -> int:
         """
-        Load a single cog with timing and error tracking.
+        Gets the loading priority for a cog based on its parent directory.
 
         Parameters
         ----------
         path : Path
-            The path to the cog to load.
+            The path to the cog file.
 
-        Raises
-        ------
-        CogLoadError
-            If the cog fails to load.
+        Returns
+        -------
+        int
+            The priority value, or 0 if not specified.
         """
-        start_time = time.perf_counter()
-
-        # Setup for Sentry tracing
-        cog_name = path.stem
-
-        # Add span tags for the current cog
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_tag("cog.name", cog_name)
-            current_span.set_tag("cog.path", str(path))
+        return self.load_priorities.get(path.parent.name, 0)
 
-        try:
-            # Get the path relative to the tux package
-            relative_path = path.relative_to(Path(__file__).parent)
-
-            # Convert path to module format (e.g., tux.cogs.admin.dev)
-            module = f"tux.{str(relative_path).replace('/', '.').replace('\\', '.')[:-3]}"
-
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_tag("cog.module", module)
-
-            # Check if this module or any parent module is already loaded
-            # This prevents duplicate loading of the same module
-            module_parts = module.split(".")
-
-            for i in range(len(module_parts), 1, -1):
-                check_module = ".".join(module_parts[:i])
-                if check_module in self.bot.extensions:
-                    logger.warning(f"Skipping {module} as {check_module} is already loaded")
-                    if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                        current_span.set_tag("cog.status", "skipped")
-                        current_span.set_tag("cog.skip_reason", "already_loaded")
-                        current_span.set_data("already_loaded_module", check_module)
-                    return
-
-            # Actually load the extension
-            await self.bot.load_extension(name=module)
-            load_time = time.perf_counter() - start_time
-            self.load_times[module] = load_time
-
-            # Add telemetry data to span
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_tag("cog.status", "loaded")
-                current_span.set_data("load_time_ms", load_time * 1000)
-                current_span.set_data("load_time_s", load_time)
-
-            logger.debug(f"Successfully loaded cog {module} in {load_time * 1000:.0f}ms")
+    def _discover_and_sort_cogs(self, path: Path) -> list[Path]:
+        """
+        Discovers all eligible cogs in a directory and sorts them by priority.
 
-        except Exception as e:
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_status("internal_error")
-                current_span.set_tag("cog.status", "failed")
-                current_span.set_data("error", str(e))
-                current_span.set_data("traceback", traceback.format_exc())
-
-            module_name = str(path)
-            error_msg = f"Failed to load cog {module_name}. Error: {e}\n{traceback.format_exc()}"
-            logger.error(error_msg)
-            raise CogLoadError(error_msg) from e
+        Parameters
+        ----------
+        path : Path
+            The directory to search for cogs.
 
-    def _get_cog_priority(self, path: Path) -> int:
+        Returns
+        -------
+        list[Path]
+            A list of cog file paths, sorted by priority (descending).
+        """
+        if not path.is_dir():
+            return []
+
+        eligible_cogs = [f for f in path.rglob("*.py") if self._is_eligible_cog_file(f)]
+        return sorted(eligible_cogs, key=lambda p: (self._get_cog_priority(p), p.name), reverse=True)
+
+    def _create_load_result(
+        self,
+        path: Path,
+        start_time: float,
+        success: bool = True,
+        error: Exception | None = None,
+    ) -> CogLoadResult:
         """
-        Get the loading priority for a cog based on its category.
+        Creates a standardized CogLoadResult object.
 
         Parameters
         ----------
         path : Path
-            The path to the cog.
+            The path to the cog file.
+        start_time : float
+            The time when the loading process started.
+        success : bool, optional
+            Whether the load was successful, by default True.
+        error : Exception | None, optional
+            The error that occurred, if any, by default None.
 
         Returns
         -------
-        int
-            The priority value (higher = loaded earlier)
+        CogLoadResult
+            The result object.
         """
-        return self.load_priorities.get(path.parent.name, 0)
+        module = self._path_to_module(path)
+        load_time = time.perf_counter() - start_time
+        return CogLoadResult(module, success, load_time, error)
+
+    # --- Cog Operations ---
 
-    @span("cog.load_group")
-    async def _load_cog_group(self, cogs: Sequence[Path]) -> None:
+    @span("cog.load_single")
+    async def _load_single_cog(self, path: Path) -> CogLoadResult:
         """
-        Load a group of cogs concurrently.
+        Loads a single cog with comprehensive error handling and timing.
 
         Parameters
         ----------
-        cogs : Sequence[Path]
-            The cogs to load.
-        """
-        if not cogs:
-            return
-
-        # Add basic info for the group
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_data("cog_count", len(cogs))
+        path : Path
+            The path to the cog file to load.
 
-            if categories := {cog.parent.name for cog in cogs if cog.parent}:
-                current_span.set_data("categories", list(categories))
+        Returns
+        -------
+        CogLoadResult
+            The result of the loading operation.
 
-        # Track cog group loading
+        Raises
+        ------
+        CogLoadError
+            If the cog fails to load.
+        """
         start_time = time.perf_counter()
-        results = await asyncio.gather(*[self._load_single_cog(cog) for cog in cogs], return_exceptions=True)
-        end_time = time.perf_counter()
-
-        # Calculate success/failure rates
-        success_count = len([r for r in results if not isinstance(r, Exception)])
-        failure_count = len(results) - success_count
-
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_data("load_time_s", end_time - start_time)
-            current_span.set_data("success_count", success_count)
-            current_span.set_data("failure_count", failure_count)
-
-        # Log failures with proper context
-        for result, cog in zip(results, cogs, strict=False):
-            if isinstance(result, Exception):
-                logger.error(f"Error loading {cog}: {result}")
-
-    async def _process_single_file(self, path: Path) -> None:
-        """Process a single file path."""
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_tag("path.is_dir", False)
-        if await self.is_cog_eligible(path):
-            await self._load_single_cog(path)
+        module = self._path_to_module(path)
+        cog_name = path.stem
 
-    async def _process_directory(self, path: Path) -> None:
-        """Process a directory of cogs."""
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_tag("path.is_dir", True)
-
-        # Collect and sort eligible cogs by priority
-        cog_paths: list[tuple[int, Path]] = [
-            (self._get_cog_priority(item), item) for item in path.rglob("*.py") if await self.is_cog_eligible(item)
-        ]
-        cog_paths.sort(key=lambda x: x[0], reverse=True)
-
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_data("eligible_cog_count", len(cog_paths))
-
-            # Priority groups info for observability
-            priority_groups: dict[int, int] = {}
-            for priority, _ in cog_paths:
-                if priority in priority_groups:
-                    priority_groups[priority] += 1
-                else:
-                    priority_groups[priority] = 1
-            current_span.set_data("priority_groups", priority_groups)
-
-        # Group and load cogs by priority
-        current_group: list[Path] = []
-        current_priority: int | None = None
-
-        for priority, cog_path in cog_paths:
-            if current_priority != priority and current_group:
-                await self._load_cog_group(current_group)
-                current_group = []
-            current_priority = priority
-            current_group.append(cog_path)
-
-        # Load final group
-        if current_group:
-            await self._load_cog_group(current_group)
+        set_span_attributes({"cog.name": cog_name, "cog.path": str(path), "cog.module": module})
 
-    @span("cog.load_path")
-    async def load_cogs(self, path: Path) -> None:
+        try:
+            await self.bot.load_extension(module)
+        except Exception as e:
+            result = self._create_load_result(path, start_time, success=False, error=e)
+            capture_span_exception(e, cog_status="failed", cog_name=cog_name, cog_module=module)
+            error_msg = f"Failed to load cog {module}."
+            logger.error(f"{error_msg} Error: {e}")
+            raise CogLoadError(error_msg) from e
+        else:
+            result = self._create_load_result(path, start_time)
+            self.load_times[module] = result.load_time
+            set_span_attributes({"cog.status": "loaded", "load_time_ms": result.load_time_ms})
+            logger.debug(f"Successfully loaded cog {module} in {result.load_time_ms:.2f}ms")
+            return result
+
+    @span("cog.unload_single")
+    async def _unload_single_cog(self, path: Path) -> bool:
         """
-        Recursively loads eligible cogs from the specified directory with concurrent loading.
+        Unloads a single cog with enhanced tracing.
 
         Parameters
         ----------
         path : Path
-            The path to the directory containing cogs.
+            The path to the cog file to unload.
+
+        Returns
+        -------
+        bool
+            True if the cog was unloaded successfully, False otherwise.
         """
-        # Add span context
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_tag("cog.path", str(path))
+        module = self._path_to_module(path)
+        set_span_attributes({"cog.module": module})
 
         try:
-            # Handle file vs directory paths differently
-            if not await aiofiles.os.path.isdir(path):
-                await self._process_single_file(path)
-            else:
-                await self._process_directory(path)
-
+            await self.bot.unload_extension(module)
+        except commands.ExtensionNotLoaded:
+            logger.warning(f"Cog {module} is not loaded, cannot unload.")
+            return False
         except Exception as e:
-            path_str = path.as_posix()
-            logger.error(f"An error occurred while processing {path_str}: {e}")
-
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_status("internal_error")
-                current_span.set_data("error", str(e))
-                current_span.set_data("traceback", traceback.format_exc())
-
-            raise CogLoadError(CogLoadError.FAILED_TO_LOAD) from e
+            capture_span_exception(e, operation="unload", cog_module=module)
+            logger.error(f"Failed to unload cog {module}: {e}")
+            return False
+        else:
+            logger.info(f"Successfully unloaded cog: {module}")
+            return True
 
-    @transaction("cog.load_folder", description="Loading all cogs from folder")
-    async def load_cogs_from_folder(self, folder_name: str) -> None:
+    @span("cog.reload_single")
+    async def reload_cog(self, path: Path) -> bool:
         """
-        Loads cogs from the specified folder with timing.
+        Reloads a single cog with comprehensive error handling.
 
         Parameters
         ----------
-        folder_name : str
-            The name of the folder containing the cogs.
-        """
-        # Add span info
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_tag("cog.folder", folder_name)
-            # Use safe_set_name instead of direct set_name call
-            safe_set_name(current_span, f"Load Cogs: {folder_name}")
+        path : Path
+            The path to the cog file to reload.
 
-        start_time = time.perf_counter()
-        cog_path: Path = Path(__file__).parent / folder_name
+        Returns
+        -------
+        bool
+            True if the cog was reloaded successfully, False otherwise.
+        """
+        module = self._path_to_module(path)
+        set_span_attributes({"cog.module": module})
 
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_data("full_path", str(cog_path))
+        await self._unload_single_cog(path)
 
         try:
-            await self.load_cogs(path=cog_path)
-            load_time = time.perf_counter() - start_time
+            await self._load_single_cog(path)
+        except CogLoadError:
+            return False
+        else:
+            logger.info(f"Successfully reloaded cog: {module}")
+            return True
 
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_data("load_time_s", load_time)
-                current_span.set_data("load_time_ms", load_time * 1000)
+    # --- Loading Workflow ---
 
-            if load_time:
-                logger.info(f"Loaded all cogs from {folder_name} in {load_time * 1000:.0f}ms")
+    @span("cog.load_directory")
+    async def _load_cogs_from_directory(self, path: Path) -> list[CogLoadResult]:
+        """
+        Discovers, groups, and loads all eligible cogs from a directory.
 
-                # Log individual cog load times for performance monitoring
-                slow_threshold = 1.0  # seconds
-                if slow_cogs := {k: v for k, v in self.load_times.items() if v > slow_threshold}:
-                    if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                        current_span.set_data("slow_cogs", slow_cogs)
-                    logger.warning(f"Slow loading cogs (>{slow_threshold * 1000:.0f}ms): {slow_cogs}")
+        Cogs are loaded by priority groups in descending order. Within each priority
+        group, cogs are loaded sequentially to prevent race conditions and dependency
+        issues. If a cog fails to load within a priority group, the remaining cogs
+        in that group are skipped to prevent cascading failures.
 
-        except Exception as e:
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_status("internal_error")
-                current_span.set_data("error", str(e))
-                current_span.set_data("traceback", traceback.format_exc())
+        Parameters
+        ----------
+        path : Path
+            The directory to load cogs from.
 
-            logger.error(f"Failed to load cogs from folder {folder_name}: {e}")
-            raise CogLoadError(CogLoadError.FAILED_TO_LOAD_FOLDER) from e
+        Returns
+        -------
+        list[CogLoadResult]
+            A list of results for each cog loaded.
+        """
+        eligible_cogs = self._discover_and_sort_cogs(path)
+        if not eligible_cogs:
+            return []
+
+        set_span_attributes({"eligible_cog_count": len(eligible_cogs)})
+
+        all_results: list[CogLoadResult] = []
+        cogs_by_priority = groupby(eligible_cogs, key=self._get_cog_priority)
+
+        for priority, cogs in cogs_by_priority:
+            cogs_to_load = list(cogs)
+            with enhanced_span("cog.load_priority_group", f"Loading priority {priority} cogs", priority=priority):
+                categories = {cog.parent.name for cog in cogs_to_load}
+                set_span_attributes({"cog_count": len(cogs_to_load), "categories": list(categories)})
+
+                start_time = time.perf_counter()
+                # Load cogs sequentially within priority group to avoid dependency issues
+                # This prevents race conditions that could occur if cogs within the same
+                # priority group depend on each other during import/initialization
+                group_results: list[CogLoadResult] = []
+                for cog in cogs_to_load:
+                    try:
+                        result = await self._load_single_cog(cog)
+                        group_results.append(result)
+                    except CogLoadError as e:
+                        # Create a failed result for tracking
+                        failed_result = self._create_load_result(cog, start_time, success=False, error=e)
+                        group_results.append(failed_result)
+                        # Stop loading remaining cogs in this priority group to prevent
+                        # cascading failures from dependency issues
+                        logger.warning(f"Skipping remaining cogs in priority {priority} due to failure: {e}")
+                        break
+
+                all_results.extend(group_results)
+
+                set_span_attributes(
+                    {
+                        "load_time_s": time.perf_counter() - start_time,
+                        "success_count": len([r for r in group_results if r.success]),
+                        "failure_count": len([r for r in group_results if not r.success]),
+                    },
+                )
+        return all_results
 
-    @classmethod
-    @transaction("cog.setup", name="CogLoader Setup", description="Initialize CogLoader and load all cogs")
-    async def setup(cls, bot: commands.Bot) -> None:
+    @span("cog.load_path")
+    async def load_cogs(self, path: Path) -> list[CogLoadResult]:
         """
-        Set up the cog loader and load all cogs.
+        Recursively loads eligible cogs from a directory or a single file.
 
         Parameters
         ----------
-        bot : commands.Bot
-            The bot instance.
+        path : Path
+            The path to the file or directory to load cogs from.
+
+        Returns
+        -------
+        list[CogLoadResult]
+            A list of results for each cog loaded.
+
+        Raises
+        ------
+        FileNotFoundError
+            If the specified path does not exist.
+        CogLoadError
+            If a fatal error occurs during the loading process.
         """
-        if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-            current_span.set_tag("bot.id", bot.user.id if bot.user else "unknown")
+        set_span_attributes({"cog.path": str(path)})
 
-        start_time = time.perf_counter()
-        cog_loader = cls(bot)
+        if not path.exists():
+            logger.error(f"Cog path not found: {path}")
+            msg = f"Cog path not found: {path}"
+            raise FileNotFoundError(msg)
 
         try:
-            # Load handlers first (they have highest priority)
-            with start_span("cog.load_handlers", "Load handler cogs"):
-                await cog_loader.load_cogs_from_folder(folder_name="handlers")
+            if path.is_dir():
+                return await self._load_cogs_from_directory(path)
+            if self._is_eligible_cog_file(path):
+                return [await self._load_single_cog(path)]
+        except Exception as e:
+            capture_span_exception(e, path=str(path), operation="load_cogs")
+            logger.error(f"An error occurred while processing {path.as_posix()}: {e}")
+            msg = f"Failed to load from {path.as_posix()}"
+            raise CogLoadError(msg) from e
 
-            # Then load regular cogs
-            with start_span("cog.load_regular", "Load regular cogs"):
-                await cog_loader.load_cogs_from_folder(folder_name="cogs")
+        logger.debug(f"Path {path} is not an eligible cog file or directory.")
+        return []
 
-            # Finally, load cogs from the extensions folder
-            with start_span("cog.load_extensions", "Load extension cogs"):
-                await cog_loader.load_cogs_from_folder(folder_name="extensions")
+    @transaction("cog.load_folder", description="Loading all cogs from a folder")
+    async def load_cogs_from_folder(self, folder_name: str) -> list[CogLoadResult]:
+        """
+        Loads all cogs from a specified top-level folder.
 
-            total_time = time.perf_counter() - start_time
+        Parameters
+        ----------
+        folder_name : str
+            The name of the folder to load cogs from (e.g., "tux/cogs").
 
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_data("total_load_time_s", total_time)
-                current_span.set_data("total_load_time_ms", total_time * 1000)
+        Returns
+        -------
+        list[CogLoadResult]
+            A list of results for each cog loaded.
 
-            # Add the CogLoader itself as a cog for bot maintenance
-            with start_span("cog.register_loader", "Register CogLoader cog"):
-                await bot.add_cog(cog_loader)
+        Raises
+        ------
+        CogLoadError
+            Propagates errors from the underlying `load_cogs` call.
+        """
+        cog_path = Path(folder_name)
+        with enhanced_span("cog.folder_processing", f"Processing {folder_name}", folder=folder_name):
+            start_time = time.perf_counter()
+            try:
+                results = await self.load_cogs(path=cog_path)
+            except FileNotFoundError as e:
+                # Handle missing folders gracefully but log as error for visibility
+                capture_span_exception(e, folder=folder_name, operation="load_folder")
+                logger.error(f"Cog folder not found: {folder_name} - {e}")
+                return []
+            except CogLoadError as e:
+                capture_span_exception(e, folder=folder_name, operation="load_folder")
+                logger.error(f"Failed to load cogs from folder {folder_name}: {e}")
+                raise
+            else:
+                load_time = time.perf_counter() - start_time
+                success_count = sum(r.success for r in results)
+                logger.info(
+                    f"Loaded {success_count}/{len(results)} cogs from {folder_name} in {load_time * 1000:.2f}ms",
+                )
+                return results
 
-            logger.info(f"Total cog loading time: {total_time * 1000:.0f}ms")
+    # --- Setup ---
 
-        except Exception as e:
-            if sentry_sdk.is_initialized() and (current_span := sentry_sdk.get_current_span()):
-                current_span.set_status("internal_error")
-                current_span.set_data("error", str(e))
-                current_span.set_data("traceback", traceback.format_exc())
+    @classmethod
+    @transaction("cog.setup", name="CogLoader Setup", description="Initialize and load all cogs")
+    async def setup(cls, bot: commands.Bot) -> CogLoader:
+        """
+        Sets up the cog loader and loads all initial cogs for the bot.
+
+        Parameters
+        ----------
+        bot : commands.Bot
+            The bot instance to set up.
 
-            logger.error(f"Failed to set up cog loader: {e}")
-            raise CogLoadError(CogLoadError.FAILED_TO_INITIALIZE) from e
+        Returns
+        -------
+        CogLoader
+            The initialized CogLoader instance.
+
+        Raises
+        ------
+        CogLoadError
+            If a fatal error occurs during the setup process.
+        """
+        with enhanced_span("cog.loader_init", "Initializing CogLoader", bot_id=bot.user.id if bot.user else "unknown"):
+            start_time = time.perf_counter()
+            cog_loader = cls(bot)
+            cog_folders = ["tux/handlers", "tux/cogs", "tux/extensions"]
+            try:
+                all_results: list[CogLoadResult] = []
+                for folder in cog_folders:
+                    folder_results = await cog_loader.load_cogs_from_folder(folder_name=folder)
+                    all_results.extend(folder_results)
+                total_time = time.perf_counter() - start_time
+                total_cogs = len(all_results)
+                successful_cogs = sum(r.success for r in all_results)
+                logger.info(
+                    f"Cog loading complete: {successful_cogs}/{total_cogs} cogs loaded in {total_time * 1000:.2f}ms",
+                )
+            except Exception as e:
+                capture_span_exception(e, operation="cog_setup")
+                logger.opt(exception=e).critical("Failed to set up cog loader.")
+                msg = "Failed to initialize CogLoader"
+                raise CogLoadError(msg) from e
+            else:
+                await bot.add_cog(cog_loader)
+                return cog_loader
diff --git a/tux/cogs/moderation/tempban.py b/tux/cogs/moderation/tempban.py
index 4641de854..3f18b67e7 100644
--- a/tux/cogs/moderation/tempban.py
+++ b/tux/cogs/moderation/tempban.py
@@ -10,6 +10,7 @@
 from tux.utils import checks
 from tux.utils.flags import TempBanFlags
 from tux.utils.functions import generate_usage
+from tux.utils.task_manager import CriticalTaskConfig, TaskPriority
 
 from . import ModerationCogBase
 
@@ -200,6 +201,16 @@ async def cog_unload(self) -> None:
         """Cancel the tempban check loop when the cog is unloaded."""
         self.tempban_check.cancel()
 
+    def get_critical_tasks(self) -> list[CriticalTaskConfig]:
+        """Get critical tasks for this cog.
+
+        Returns
+        -------
+        list[CriticalTaskConfig]
+            List of critical task configurations
+        """
+        return [CriticalTaskConfig("tempban_checker", "TempBan", "tempban_check", TaskPriority.HIGH)]
+
 
 async def setup(bot: Tux) -> None:
     await bot.add_cog(TempBan(bot))
diff --git a/tux/cogs/services/gif_limiter.py b/tux/cogs/services/gif_limiter.py
index b9f7a694d..6c57970f2 100644
--- a/tux/cogs/services/gif_limiter.py
+++ b/tux/cogs/services/gif_limiter.py
@@ -7,6 +7,7 @@
 
 from tux.bot import Tux
 from tux.utils.config import CONFIG
+from tux.utils.task_manager import CriticalTaskConfig, TaskPriority
 
 
 class GifLimiter(commands.Cog):
@@ -147,6 +148,16 @@ async def cog_unload(self) -> None:
         """Cancel the background task when the cog is unloaded."""
         self.old_gif_remover.cancel()
 
+    def get_critical_tasks(self) -> list[CriticalTaskConfig]:
+        """Get critical tasks for this cog.
+
+        Returns
+        -------
+        list[CriticalTaskConfig]
+            List of critical task configurations
+        """
+        return [CriticalTaskConfig("old_gif_remover", "GifLimiter", "old_gif_remover", TaskPriority.NORMAL)]
+
 
 async def setup(bot: Tux) -> None:
     await bot.add_cog(GifLimiter(bot))
diff --git a/tux/cogs/services/influxdblogger.py b/tux/cogs/services/influxdblogger.py
index fada085b5..2dff08582 100644
--- a/tux/cogs/services/influxdblogger.py
+++ b/tux/cogs/services/influxdblogger.py
@@ -9,6 +9,7 @@
 from tux.bot import Tux
 from tux.database.controllers import DatabaseController
 from tux.utils.config import CONFIG
+from tux.utils.task_manager import CriticalTaskConfig, TaskPriority
 
 
 class InfluxLogger(commands.Cog):
@@ -20,8 +21,11 @@ def __init__(self, bot: Tux):
 
         if self.init_influx():
             self.logger.start()
+            logger.info("InfluxDB logger initialized successfully")
         else:
             logger.warning("InfluxDB logger failed to init. Check .env configuration if you want to use it.")
+            # Don't start the task if InfluxDB is not configured
+            # The cog will remain loaded but the task won't run
 
     def init_influx(self) -> bool:
         """Initialize InfluxDB client for metrics logging.
@@ -42,6 +46,19 @@ def init_influx(self) -> bool:
             return True
         return False
 
+    def get_critical_tasks(self) -> list[CriticalTaskConfig]:
+        """Get critical tasks for this cog.
+
+        Returns
+        -------
+        list[CriticalTaskConfig]
+            List of critical task configurations, or empty list if not functional
+        """
+        # Only register the task if InfluxDB is properly configured
+        if self.influx_write_api is not None:
+            return [CriticalTaskConfig("influx_db_logger", "InfluxLogger", "logger", TaskPriority.LOW)]
+        return []
+
     @tasks.loop(seconds=60)
     async def logger(self) -> None:
         """Log statistics to InfluxDB at regular intervals.
@@ -49,7 +66,8 @@ async def logger(self) -> None:
         Collects data from various database models and writes metrics to InfluxDB.
         """
         if not self.influx_write_api:
-            logger.warning("InfluxDB writer not initialized, skipping metrics collection")
+            logger.warning("InfluxDB writer not initialized, stopping task")
+            self.logger.stop()
             return
 
         influx_bucket = "tux stats"
diff --git a/tux/cogs/utility/afk.py b/tux/cogs/utility/afk.py
index bafaec050..2a72b2364 100644
--- a/tux/cogs/utility/afk.py
+++ b/tux/cogs/utility/afk.py
@@ -12,6 +12,7 @@
 from tux.cogs.utility import add_afk, del_afk
 from tux.database.controllers import DatabaseController
 from tux.utils.functions import generate_usage
+from tux.utils.task_manager import CriticalTaskConfig, TaskPriority
 
 # TODO: add `afk until` command, or add support for providing a timeframe in the regular `afk` and `permafk` commands
 
@@ -220,6 +221,16 @@ async def _get_expired_afk_entries(self, guild_id: int) -> list[AFKModel]:
 
         return [entry for entry in entries if entry.until is not None and entry.until < current_time]
 
+    def get_critical_tasks(self) -> list[CriticalTaskConfig]:
+        """Get critical tasks for this cog.
+
+        Returns
+        -------
+        list[CriticalTaskConfig]
+            List of critical task configurations
+        """
+        return [CriticalTaskConfig("afk_expiration_handler", "Afk", "handle_afk_expiration", TaskPriority.NORMAL)]
+
 
 async def setup(bot: Tux) -> None:
     await bot.add_cog(Afk(bot))
diff --git a/tux/database/controllers/__init__.py b/tux/database/controllers/__init__.py
index 445c4c84f..c09c08c9f 100644
--- a/tux/database/controllers/__init__.py
+++ b/tux/database/controllers/__init__.py
@@ -1,11 +1,7 @@
 """Database controller module providing access to all model controllers."""
 
-import functools
-import inspect
 from typing import Any, ClassVar, TypeVar
 
-import sentry_sdk
-
 from tux.database.controllers.afk import AfkController
 from tux.database.controllers.case import CaseController
 from tux.database.controllers.guild import GuildController
@@ -15,6 +11,7 @@
 from tux.database.controllers.reminder import ReminderController
 from tux.database.controllers.snippet import SnippetController
 from tux.database.controllers.starboard import StarboardController, StarboardMessageController
+from tux.utils.tracing import span
 
 # Define a TypeVar that can be any BaseController subclass
 ControllerType = TypeVar("ControllerType")
@@ -67,7 +64,9 @@ def __init__(self) -> None:
 
     def _get_controller(self, controller_type: type[ControllerType]) -> ControllerType:
         """
-        Helper method to instantiate a controller with proper Sentry instrumentation.
+        Helper method to instantiate a controller with selective Sentry instrumentation.
+
+        Only instruments meaningful database operations to reduce span noise.
 
         Parameters
         ----------
@@ -77,83 +76,62 @@ def _get_controller(self, controller_type: type[ControllerType]) -> ControllerTy
         Returns
         -------
         ControllerType
-            The instantiated controller
+            The instantiated controller with selectively instrumented methods
         """
         instance = controller_type()
-        if sentry_sdk.is_initialized():
-            # Get all public methods to wrap
-            methods = [attr for attr in dir(instance) if callable(getattr(instance, attr)) and not attr.startswith("_")]
 
-            # Wrap each public method with Sentry transaction
-            for method_name in methods:
+        # Only instrument meaningful database operations
+        # Filter out utility methods that create noise
+        excluded_methods = {
+            "safe_get_attr",
+            "connect_or_create_relation",
+            "_add_include_arg_if_present",
+            "_build_find_args",
+            "_build_simple_args",
+            "_build_create_args",
+            "_build_update_args",
+            "_build_delete_args",
+            "_build_upsert_args",
+            "_execute_query",
+            "_set_scope_context",
+        }
+
+        # Include patterns for meaningful operations
+        include_patterns = {
+            "get_",
+            "find_",
+            "create_",
+            "update_",
+            "delete_",
+            "count_",
+            "increment_",
+            "toggle_",
+            "lock_",
+            "unlock_",
+            "bulk_",
+        }
+
+        # Get all public methods to potentially wrap
+        methods = [
+            attr
+            for attr in dir(instance)
+            if callable(getattr(instance, attr)) and not attr.startswith("_") and attr not in excluded_methods
+        ]
+
+        # Wrap only methods that match meaningful operation patterns
+        for method_name in methods:
+            if any(method_name.startswith(pattern) for pattern in include_patterns):
                 original_method = getattr(instance, method_name)
-                # Use a factory function to capture loop variables
-                self._create_wrapped_method(instance, method_name, original_method)
 
-        return instance
+                # Create the operation name for the span
+                op = f"db.controller.{method_name}"
 
-    def _create_wrapped_method(self, instance: Any, method_name: str, original_method: Any) -> None:
-        """
-        Create a wrapped method with proper sentry instrumentation.
+                # Apply the span decorator to the original method
+                wrapped_method = span(op=op)(original_method)
 
-        Parameters
-        ----------
-        instance : Any
-            The controller instance
-        method_name : str
-            The name of the method to wrap
-        original_method : Any
-            The original method to wrap
-        """
+                setattr(instance, method_name, wrapped_method)
 
-        # Check if the original method is async
-        is_async = inspect.iscoroutinefunction(original_method)
-
-        if is_async:
-
-            @functools.wraps(original_method)
-            async def async_wrapped_method(*args: Any, **kwargs: Any) -> Any:
-                controller_name = instance.__class__.__name__
-                with sentry_sdk.start_span(
-                    op=f"db.controller.{method_name}",
-                    description=f"{controller_name}.{method_name}",
-                ) as span:
-                    span.set_tag("db.controller", controller_name)
-                    span.set_tag("db.operation", method_name)
-                    try:
-                        result = await original_method(*args, **kwargs)
-                    except Exception as e:
-                        span.set_status("internal_error")
-                        span.set_data("error", str(e))
-                        raise
-                    else:
-                        span.set_status("ok")
-                        return result
-
-            setattr(instance, method_name, async_wrapped_method)
-
-        else:
-
-            @functools.wraps(original_method)
-            def sync_wrapped_method(*args: Any, **kwargs: Any) -> Any:
-                controller_name = instance.__class__.__name__
-                with sentry_sdk.start_span(
-                    op=f"db.controller.{method_name}",
-                    description=f"{controller_name}.{method_name}",
-                ) as span:
-                    span.set_tag("db.controller", controller_name)
-                    span.set_tag("db.operation", method_name)
-                    try:
-                        result = original_method(*args, **kwargs)
-                    except Exception as e:
-                        span.set_status("internal_error")
-                        span.set_data("error", str(e))
-                        raise
-                    else:
-                        span.set_status("ok")
-                        return result
-
-            setattr(instance, method_name, sync_wrapped_method)
+        return instance
 
     _controller_mapping: ClassVar[dict[str, type]] = {
         "afk": AfkController,
diff --git a/tux/database/controllers/base.py b/tux/database/controllers/base.py
index f407e480d..96450bc09 100644
--- a/tux/database/controllers/base.py
+++ b/tux/database/controllers/base.py
@@ -3,7 +3,6 @@
 from collections.abc import Callable
 from typing import Any, TypeVar
 
-import sentry_sdk
 from loguru import logger
 
 from prisma.models import (
@@ -84,6 +83,7 @@ async def _execute_query(
         self,
         operation: Callable[[], Any],
         error_msg: str,
+        op_name: str,
     ) -> Any:
         """Executes a database query with standardized error logging.
 
@@ -96,6 +96,8 @@ async def _execute_query(
             A zero-argument function (e.g., a lambda) that performs the database call.
         error_msg : str
             The base error message to log if an exception occurs.
+        op_name : str
+            The name of the database operation (e.g., 'find_one', 'create').
 
         Returns
         -------
@@ -107,25 +109,13 @@ async def _execute_query(
         Exception
             Re-raises any exception caught during the database operation.
         """
-        # Create a Sentry span to track database query performance
-        if sentry_sdk.is_initialized():
-            with sentry_sdk.start_span(op="db.query", description=f"Database query: {self.table_name}") as span:
-                span.set_tag("db.table", self.table_name)
-                try:
-                    result = await operation()
-                    span.set_status("ok")
-                    return result  # noqa: TRY300
-                except Exception as e:
-                    span.set_status("internal_error")
-                    span.set_data("error", str(e))
-                    logger.error(f"{error_msg}: {e}")
-                    raise
-        else:
-            try:
-                return await operation()
-            except Exception as e:
-                logger.error(f"{error_msg}: {e}")
-                raise
+        # Remove span creation here to avoid duplication with controller-level spans
+        # Controller methods should handle their own tracing for meaningful operations
+        try:
+            return await operation()
+        except Exception as e:
+            logger.error(f"{error_msg}: {e}")
+            raise
 
     def _add_include_arg_if_present(self, args: dict[str, Any], include: dict[str, bool] | None) -> None:
         """Adds the 'include' argument to a dictionary if it is not None."""
@@ -238,6 +228,7 @@ async def find_one(
         return await self._execute_query(
             lambda: self.table.find_first(**find_args),
             f"Failed to find record in {self.table_name} with criteria {where}",
+            "find_one",
         )
 
     async def find_unique(
@@ -263,6 +254,7 @@ async def find_unique(
         return await self._execute_query(
             lambda: self.table.find_unique(**find_args),
             f"Failed to find unique record in {self.table_name} with criteria {where}",
+            "find_unique",
         )
 
     async def find_many(
@@ -307,6 +299,7 @@ async def find_many(
         return await self._execute_query(
             lambda: self.table.find_many(**find_args),
             f"Failed to find records in {self.table_name} with criteria {where}",
+            "find_many",
         )
 
     async def count(
@@ -328,6 +321,7 @@ async def count(
         return await self._execute_query(
             lambda: self.table.count(where=where),
             f"Failed to count records in {self.table_name} with criteria {where}",
+            "count",
         )
 
     async def create(
@@ -353,6 +347,7 @@ async def create(
         return await self._execute_query(
             lambda: self.table.create(**create_args),
             f"Failed to create record in {self.table_name} with data {data}",
+            "create",
         )
 
     async def update(
@@ -381,6 +376,7 @@ async def update(
         return await self._execute_query(
             lambda: self.table.update(**update_args),
             f"Failed to update record in {self.table_name} with criteria {where} and data {data}",
+            "update",
         )
 
     async def delete(
@@ -406,6 +402,7 @@ async def delete(
         return await self._execute_query(
             lambda: self.table.delete(**delete_args),
             f"Failed to delete record in {self.table_name} with criteria {where}",
+            "delete",
         )
 
     async def upsert(
@@ -437,6 +434,7 @@ async def upsert(
         return await self._execute_query(
             lambda: self.table.upsert(**upsert_args),
             f"Failed to upsert record in {self.table_name} with where={where}, create={create}, update={update}",
+            "upsert",
         )
 
     async def update_many(
@@ -466,6 +464,7 @@ async def update_many(
         result = await self._execute_query(
             lambda: self.table.update_many(where=where, data=data),
             f"Failed to update records in {self.table_name} with criteria {where} and data {data}",
+            "update_many",
         )
         # Validate and return count
         count_val = getattr(result, "count", None)
@@ -498,6 +497,7 @@ async def delete_many(
         result = await self._execute_query(
             lambda: self.table.delete_many(where=where),
             f"Failed to delete records in {self.table_name} with criteria {where}",
+            "delete_many",
         )
         # Validate and return count
         count_val = getattr(result, "count", None)
diff --git a/tux/database/controllers/levels.py b/tux/database/controllers/levels.py
index 87d39af72..6efd3d18e 100644
--- a/tux/database/controllers/levels.py
+++ b/tux/database/controllers/levels.py
@@ -21,6 +21,28 @@ def __init__(self) -> None:
         super().__init__("levels")
         self.guild_table: GuildActions[Guild] = db.client.guild
 
+    async def get_user_level_data(self, member_id: int, guild_id: int) -> Levels | None:
+        """
+        Fetches all level-related data for a user in a single query.
+
+        Parameters
+        ----------
+        member_id : int
+            The ID of the member.
+        guild_id : int
+            The ID of the guild.
+
+        Returns
+        -------
+        Levels | None
+            The levels record for the user, or None if not found.
+        """
+        try:
+            return await self.find_one(where={"member_id": member_id, "guild_id": guild_id})
+        except Exception as e:
+            logger.error(f"Error querying level data for member_id: {member_id}, guild_id: {guild_id}: {e}")
+            return None
+
     async def get_xp(self, member_id: int, guild_id: int) -> float:
         """Get the XP of a member in a guild.
 
diff --git a/tux/handlers/error.py b/tux/handlers/error.py
index 93e94e992..09569b425 100644
--- a/tux/handlers/error.py
+++ b/tux/handlers/error.py
@@ -12,17 +12,17 @@
 import traceback
 from collections.abc import Callable, Coroutine
 from dataclasses import dataclass
-from typing import Any
+from typing import Any, cast
 
 import discord
 import Levenshtein
-import sentry_sdk
 from discord import app_commands
 from discord.ext import commands
 from loguru import logger
 
 from tux.bot import Tux
 from tux.ui.embeds import EmbedCreator
+from tux.utils.context_utils import get_interaction_context
 from tux.utils.exceptions import (
     AppCommandPermissionLevelError,
     CodeExecutionError,
@@ -32,6 +32,7 @@
     PermissionLevelError,
     UnsupportedLanguageError,
 )
+from tux.utils.sentry_manager import LogLevelStr, SentryManager
 
 # --- Constants and Configuration ---
 
@@ -75,15 +76,6 @@
 # Note: Interaction is parameterized with the Bot type (Tux).
 AppCommandErrorHandler = Callable[[discord.Interaction[Tux], app_commands.AppCommandError], Coroutine[Any, Any, None]]
 
-# --- Sentry Status Constants (copied from sentry.py for local use) ---
-SENTRY_STATUS_OK = "ok"
-SENTRY_STATUS_UNKNOWN = "unknown"
-SENTRY_STATUS_INTERNAL_ERROR = "internal_error"
-SENTRY_STATUS_NOT_FOUND = "not_found"
-SENTRY_STATUS_PERMISSION_DENIED = "permission_denied"
-SENTRY_STATUS_INVALID_ARGUMENT = "invalid_argument"
-SENTRY_STATUS_RESOURCE_EXHAUSTED = "resource_exhausted"
-
 
 # --- Error Handler Configuration ---
 
@@ -101,6 +93,9 @@ class ErrorHandlerConfig:
     # Default log level for this error type (e.g., "INFO", "WARNING", "ERROR").
     log_level: str = "INFO"
 
+    # Sentry transaction status for this error. If None, it's considered an internal error.
+    sentry_status: str | None = SentryManager.STATUS["ERROR"]
+
     # Whether to send this specific error type to Sentry when handled.
     # Useful for tracking frequency even if the user sees a friendly message.
     send_to_sentry: bool = True
@@ -222,6 +217,7 @@ def _extract_missing_argument_details(error: Exception) -> dict[str, Any]:
     app_commands.AppCommandError: ErrorHandlerConfig(
         message_format="An application command error occurred: {error}",
         log_level="WARNING",
+        sentry_status=SentryManager.STATUS["UNKNOWN"],
     ),
     # CommandInvokeError wraps the actual exception raised within an app command.
     # It will be unwrapped in _handle_error, but this provides a fallback config.
@@ -229,41 +225,49 @@ def _extract_missing_argument_details(error: Exception) -> dict[str, Any]:
         message_format="An internal error occurred while running the command.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     app_commands.TransformerError: ErrorHandlerConfig(
         message_format="Failed to process an argument value: {error}",
         log_level="INFO",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     app_commands.MissingRole: ErrorHandlerConfig(
         message_format="You need the role {roles} to use this command.",
         detail_extractor=_extract_missing_role_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     app_commands.MissingAnyRole: ErrorHandlerConfig(
         message_format="You need one of the following roles: {roles}",
         detail_extractor=_extract_missing_any_role_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     app_commands.MissingPermissions: ErrorHandlerConfig(
         message_format="You lack the required permission(s): {permissions}",
         detail_extractor=_extract_permissions_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     # Generic check failure for app commands.
     app_commands.CheckFailure: ErrorHandlerConfig(
         message_format="You do not meet the requirements to run this command.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     app_commands.CommandOnCooldown: ErrorHandlerConfig(
         message_format="This command is on cooldown. Please wait {error.retry_after:.1f}s.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["RESOURCE_EXHAUSTED"],
     ),
     app_commands.BotMissingPermissions: ErrorHandlerConfig(
         message_format="I lack the required permission(s): {permissions}",
         detail_extractor=_extract_permissions_details,
         log_level="WARNING",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # Indicates a mismatch between the command signature registered with Discord
     # and the signature defined in the bot's code.
@@ -271,11 +275,13 @@ def _extract_missing_argument_details(error: Exception) -> dict[str, Any]:
         message_format="Internal error: Command signature mismatch. Please report this.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # === Traditional Commands (discord.ext.commands) ===
     commands.CommandError: ErrorHandlerConfig(
         message_format="A command error occurred: {error}",
         log_level="WARNING",
+        sentry_status=SentryManager.STATUS["UNKNOWN"],
     ),
     # CommandInvokeError wraps the actual exception raised within a prefix command.
     # It will be unwrapped in _handle_error, but this provides a fallback config.
@@ -283,180 +289,217 @@ def _extract_missing_argument_details(error: Exception) -> dict[str, Any]:
         message_format="An internal error occurred while running the command.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     commands.ConversionError: ErrorHandlerConfig(
         message_format="Failed to convert argument: {error.original}",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     commands.MissingRole: ErrorHandlerConfig(
         message_format="You need the role {roles} to use this command.",
         detail_extractor=_extract_missing_role_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     commands.MissingAnyRole: ErrorHandlerConfig(
         message_format="You need one of the following roles: {roles}",
         detail_extractor=_extract_missing_any_role_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     commands.MissingPermissions: ErrorHandlerConfig(
         message_format="You lack the required permission(s): {permissions}",
         detail_extractor=_extract_permissions_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     # Error related to command flags (discord.ext.flags).
     commands.FlagError: ErrorHandlerConfig(
         message_format="Error processing command flags: {error}\nUsage: `{ctx.prefix}{usage}`",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     commands.BadFlagArgument: ErrorHandlerConfig(
         message_format="Invalid value for flag `{flag_name}`: {original_cause}\nUsage: `{ctx.prefix}{usage}`",
         detail_extractor=_extract_bad_flag_argument_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     commands.MissingRequiredFlag: ErrorHandlerConfig(
         message_format="Missing required flag: `{flag_name}`\nUsage: `{ctx.prefix}{usage}`",
         detail_extractor=_extract_missing_flag_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     # Generic check failure for prefix commands.
     commands.CheckFailure: ErrorHandlerConfig(
         message_format="You do not meet the requirements to run this command.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     commands.CommandOnCooldown: ErrorHandlerConfig(
         message_format="This command is on cooldown. Please wait {error.retry_after:.1f}s.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["RESOURCE_EXHAUSTED"],
     ),
     commands.MissingRequiredArgument: ErrorHandlerConfig(
         message_format="Missing required argument: `{param_name}`\nUsage: `{ctx.prefix}{usage}`",
         detail_extractor=_extract_missing_argument_details,
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     commands.TooManyArguments: ErrorHandlerConfig(
         message_format="You provided too many arguments.\nUsage: `{ctx.prefix}{usage}`",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     commands.NotOwner: ErrorHandlerConfig(
         message_format="This command can only be used by the bot owner.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     commands.BotMissingPermissions: ErrorHandlerConfig(
         message_format="I lack the required permission(s): {permissions}",
         detail_extractor=_extract_permissions_details,
         log_level="WARNING",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # Generic bad argument error.
     commands.BadArgument: ErrorHandlerConfig(
         message_format="Invalid argument provided: {error}",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     # Errors for when specific Discord entities are not found.
     commands.MemberNotFound: ErrorHandlerConfig(
         message_format="Could not find member: {error.argument}.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     commands.UserNotFound: ErrorHandlerConfig(
         message_format="Could not find user: {error.argument}.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     commands.ChannelNotFound: ErrorHandlerConfig(
         message_format="Could not find channel: {error.argument}.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     commands.RoleNotFound: ErrorHandlerConfig(
         message_format="Could not find role: {error.argument}.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     commands.EmojiNotFound: ErrorHandlerConfig(
         message_format="Could not find emoji: {error.argument}.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     commands.GuildNotFound: ErrorHandlerConfig(
         message_format="Could not find server: {error.argument}.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     # === Extension/Cog Loading Errors (discord.ext.commands) ===
     commands.ExtensionError: ErrorHandlerConfig(
         message_format="Extension operation failed: {error}",
         log_level="WARNING",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     commands.ExtensionNotLoaded: ErrorHandlerConfig(
         message_format="Cannot reload extension `{error.name}` - it hasn't been loaded yet.",
         log_level="WARNING",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     commands.ExtensionNotFound: ErrorHandlerConfig(
         message_format="Extension `{error.name}` could not be found.",
         log_level="WARNING",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     commands.ExtensionAlreadyLoaded: ErrorHandlerConfig(
         message_format="Extension `{error.name}` is already loaded.",
         log_level="INFO",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     commands.ExtensionFailed: ErrorHandlerConfig(
         message_format="Extension `{error.name}` failed to load: {error.original}",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     commands.NoEntryPointError: ErrorHandlerConfig(
         message_format="Extension `{error.name}` is missing a setup function.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # === Custom Errors (defined in tux.utils.exceptions) ===
     PermissionLevelError: ErrorHandlerConfig(
         message_format="You need permission level `{error.permission}` to use this command.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     AppCommandPermissionLevelError: ErrorHandlerConfig(
         message_format="You need permission level `{error.permission}` to use this command.",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     # === Code Execution Errors (from tux.utils.exceptions) ===
     MissingCodeError: ErrorHandlerConfig(
         message_format="{error}",
         log_level="INFO",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     InvalidCodeFormatError: ErrorHandlerConfig(
         message_format="{error}",
         log_level="INFO",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     UnsupportedLanguageError: ErrorHandlerConfig(
         message_format="{error}",
         log_level="INFO",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     CompilationError: ErrorHandlerConfig(
         message_format="{error}",
         log_level="INFO",
         send_to_sentry=True,  # Monitor frequency of compilation failures
+        sentry_status=SentryManager.STATUS["INVALID_ARGUMENT"],
     ),
     CodeExecutionError: ErrorHandlerConfig(
         message_format="{error}",
         log_level="INFO",
         send_to_sentry=True,  # Monitor general code execution issues
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # === Discord API & Client Errors ===
     discord.ClientException: ErrorHandlerConfig(
         message_format="A client-side error occurred: {error}",
         log_level="WARNING",
         send_to_sentry=True,  # Monitor frequency of generic client errors
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     discord.HTTPException: ErrorHandlerConfig(
         message_format="An HTTP error occurred while communicating with Discord: {error.status} {error.text}",
         log_level="WARNING",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     discord.RateLimited: ErrorHandlerConfig(
         message_format="We are being rate-limited by Discord. Please try again in {error.retry_after:.1f} seconds.",
         log_level="WARNING",
         send_to_sentry=True,  # Track rate limits
+        sentry_status=SentryManager.STATUS["RESOURCE_EXHAUSTED"],
     ),
     # Generic Forbidden/NotFound often indicate deleted resources or permission issues caught by more specific exceptions.
     # These provide fallbacks.
@@ -464,34 +507,40 @@ def _extract_missing_argument_details(error: Exception) -> dict[str, Any]:
         message_format="I don't have permission to perform that action. Error: {error.text}",
         log_level="WARNING",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["PERMISSION_DENIED"],
     ),
     discord.NotFound: ErrorHandlerConfig(
         message_format="Could not find the requested resource (it might have been deleted). Error: {error.text}",
         log_level="INFO",
         send_to_sentry=False,
+        sentry_status=SentryManager.STATUS["NOT_FOUND"],
     ),
     discord.DiscordServerError: ErrorHandlerConfig(
         message_format="Discord reported a server error ({error.status}). Please try again later. Error: {error.text}",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # Indicates unexpected data from Discord, potentially a library or API issue.
     discord.InvalidData: ErrorHandlerConfig(
         message_format="Received invalid data from Discord. Please report this if it persists.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # Specific to interactions, raised if interaction.response.send_message is called more than once.
     discord.InteractionResponded: ErrorHandlerConfig(
         message_format="This interaction has already been responded to.",
         log_level="WARNING",  # Usually indicates a logic error in command code
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # Raised when Application ID is needed but not available (e.g., for app command sync).
     discord.MissingApplicationID: ErrorHandlerConfig(
         message_format="Internal setup error: Missing Application ID.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # === Common Python Built-in Errors ===
     # These usually indicate internal logic errors, so show a generic message to the user
@@ -500,52 +549,62 @@ def _extract_missing_argument_details(error: Exception) -> dict[str, Any]:
         message_format="An internal error occurred due to an invalid value.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     TypeError: ErrorHandlerConfig(
         message_format="An internal error occurred due to a type mismatch.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     KeyError: ErrorHandlerConfig(
         message_format="An internal error occurred while looking up data.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     IndexError: ErrorHandlerConfig(
         message_format="An internal error occurred while accessing a sequence.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     AttributeError: ErrorHandlerConfig(
         message_format="An internal error occurred while accessing an attribute.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     ZeroDivisionError: ErrorHandlerConfig(
         message_format="An internal error occurred during a calculation (division by zero).",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # === Additional Discord Client/Connection Errors ===
     discord.LoginFailure: ErrorHandlerConfig(
         message_format="Bot authentication failed. Please check the bot token configuration.",
         log_level="CRITICAL",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["UNAUTHENTICATED"],
     ),
     discord.ConnectionClosed: ErrorHandlerConfig(
         message_format="Connection to Discord was closed unexpectedly. Attempting to reconnect...",
         log_level="WARNING",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["UNKNOWN"],
     ),
     discord.PrivilegedIntentsRequired: ErrorHandlerConfig(
         message_format="This bot requires privileged intents to function properly. Please enable them in the Discord Developer Portal.",
         log_level="CRITICAL",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     discord.GatewayNotFound: ErrorHandlerConfig(
         message_format="Could not connect to Discord's gateway. This may be a temporary issue.",
         log_level="ERROR",
         send_to_sentry=True,
+        sentry_status=SentryManager.STATUS["ERROR"],
     ),
     # Note: InvalidArgument, NoMoreItems, and TooManyRequests are not available in all discord.py versions
     # or are handled by other existing exceptions like HTTPException
@@ -640,7 +699,7 @@ async def _handle_error(self, source: ContextOrInteraction, error: Exception) ->
         root_error = _unwrap_error(error)
 
         # --- Sentry Transaction Finalization (Added) ---
-        self._finish_sentry_transaction_on_error(source, root_error)
+        self.bot.sentry_manager.finish_transaction_on_error()
         # -----------------------------------------------
 
         # Step 3: Gather context using the resolved root error.
@@ -649,11 +708,8 @@ async def _handle_error(self, source: ContextOrInteraction, error: Exception) ->
         log_context = self._get_log_context(source, user, root_error)
         log_context["initial_error_type"] = type(error).__name__  # Keep initial error type for context
 
-        # Step 4: Determine handling configuration.
-        config = ERROR_CONFIG_MAP.get(error_type)
-
         # Step 5: Format the user-facing message.
-        message = self._get_formatted_message(source, root_error, config)
+        message = self._get_formatted_message(source, root_error, ERROR_CONFIG_MAP.get(error_type))
 
         # Step 6: Create the error embed.
         embed = EmbedCreator.create_embed(
@@ -673,20 +729,29 @@ async def _handle_error(self, source: ContextOrInteraction, error: Exception) ->
             log_context["send_error"] = str(send_exc)
             log_context["send_error_type"] = type(send_exc).__name__
             logger.bind(**log_context).exception("Unexpected failure during error message sending.")
-            self._capture_exception_with_context(
+            self.bot.sentry_manager.capture_exception(
                 send_exc,
-                log_context,
-                "ERROR",
+                context=log_context,
+                level="error",
                 tags={"failure_point": "send_response"},
             )
             return
 
         # Step 8 & 9: Log and report.
-        sentry_event_id = self._log_and_report_error(root_error, error_type, log_context, config)
+        sentry_event_id = self._log_and_report_error(
+            root_error,
+            error_type,
+            log_context,
+            ERROR_CONFIG_MAP.get(error_type),
+        )
 
         # Step 10: Attempt edit with Sentry ID.
         await self._try_edit_message_with_sentry_id(sent_message, sentry_event_id, log_context)
 
+        # Set context information for better Sentry reporting
+        if self.bot.sentry_manager.is_initialized:
+            self.bot.sentry_manager.set_command_context(source)
+
     @staticmethod
     def _get_user_from_source(source: ContextOrInteraction) -> discord.User | discord.Member:
         """Helper method to consistently extract the user object from either source type."""
@@ -704,71 +769,17 @@ def _get_log_context(
         """
         Builds a dictionary containing structured context information about the error event.
 
-        Includes information about invocation type (prefix/app) and definition type (hybrid/prefix_only/app_only).
-
-        Parameters
-        ----------
-        source : ContextOrInteraction
-            The source of the error.
-        user : Union[discord.User, discord.Member]
-            The user who triggered the error.
-        error : Exception
-            The exception that occurred.
+        Args:
+            source: The source of the error.
+            user: The user who triggered the error.
+            error: The exception that occurred.
 
-        Returns
-        -------
-        dict[str, Any]
+        Returns:
             A dictionary with context keys like user_id, command_name, guild_id, etc.
         """
-        context: dict[str, Any] = {
-            "user_id": user.id,
-            "user_name": str(user),
-            "error": str(error),
-            "error_type": type(error).__name__,
-        }
-
-        # Determine invocation method first using ternary operator
-        invoked_via_interaction: bool = (
-            True if isinstance(source, discord.Interaction) else source.interaction is not None
-        )
-
-        # Set command_type based on invocation method
-        context["command_type"] = "app" if invoked_via_interaction else "prefix"
-        context["invoked_via_interaction"] = invoked_via_interaction
-
-        # Add specific details based on source type
-        if isinstance(source, discord.Interaction):
-            context["interaction_id"] = source.id
-            context["channel_id"] = source.channel_id
-            context["guild_id"] = source.guild_id
-            # Determine definition type for app invocation
-            if source.command:
-                context["command_name"] = source.command.qualified_name
-                prefix_command = self.bot.get_command(source.command.qualified_name)
-                if prefix_command and isinstance(prefix_command, commands.HybridCommand | commands.HybridGroup):
-                    context["command_definition"] = "hybrid"
-                else:
-                    context["command_definition"] = "app"
-            else:
-                context["command_definition"] = "unknown"
-
-        else:  # Source is commands.Context
-            context["message_id"] = source.message.id
-            context["channel_id"] = source.channel.id
-            context["guild_id"] = source.guild.id if source.guild else None
-            # Determine definition type for prefix invocation
-            if source.command:
-                context["command_name"] = source.command.qualified_name
-                context["command_prefix"] = source.prefix
-                context["command_invoked_with"] = source.invoked_with
-                if isinstance(source.command, commands.HybridCommand | commands.HybridGroup):
-                    context["command_definition"] = "hybrid"
-                else:
-                    context["command_definition"] = "prefix"
-            else:
-                context["command_invoked_with"] = source.invoked_with
-                context["command_definition"] = "unknown"
-
+        context = get_interaction_context(source)
+        context["error"] = str(error)
+        context["error_type"] = type(error).__name__
         return context
 
     def _get_formatted_message(
@@ -897,152 +908,6 @@ async def _send_error_response(self, source: ContextOrInteraction, embed: discor
             mention_author=False,  # Avoid potentially annoying pings for errors.
         )
 
-    # --- Sentry Transaction Finalization Logic (Added) ---
-    def _finish_sentry_transaction_on_error(self, source: ContextOrInteraction, root_error: Exception) -> None:
-        """Attempts to find and finish an active Sentry transaction based on the error source."""
-        if not sentry_sdk.is_initialized():
-            return
-
-        transaction: Any | None = None
-        transaction_id: int | None = None
-        command_type: str | None = None
-
-        # Status mapping dictionaries
-        app_command_status_map = {
-            app_commands.CommandNotFound: SENTRY_STATUS_NOT_FOUND,
-            app_commands.CheckFailure: SENTRY_STATUS_PERMISSION_DENIED,
-            app_commands.TransformerError: SENTRY_STATUS_INVALID_ARGUMENT,
-        }
-
-        prefix_command_status_map = {
-            commands.CommandNotFound: SENTRY_STATUS_NOT_FOUND,
-            commands.UserInputError: SENTRY_STATUS_INVALID_ARGUMENT,
-            commands.CheckFailure: SENTRY_STATUS_PERMISSION_DENIED,
-            commands.CommandOnCooldown: SENTRY_STATUS_RESOURCE_EXHAUSTED,
-            commands.MaxConcurrencyReached: SENTRY_STATUS_RESOURCE_EXHAUSTED,
-        }
-
-        # Default status
-        status: str = SENTRY_STATUS_INTERNAL_ERROR
-
-        try:
-            # Determine ID and type based on source
-            if isinstance(source, discord.Interaction):
-                transaction_id = source.id
-                command_type = "app_command"
-
-                # Lookup status in mapping
-                for error_type, error_status in app_command_status_map.items():
-                    if isinstance(root_error, error_type):
-                        status = error_status
-                        break
-
-            elif isinstance(source, commands.Context):  # type: ignore
-                transaction_id = source.message.id
-                command_type = "prefix_command"
-
-                # Lookup status in mapping
-                for error_type, error_status in prefix_command_status_map.items():
-                    if isinstance(root_error, error_type):
-                        status = error_status
-                        break
-
-            else:
-                logger.warning(f"Unknown error source type encountered: {type(source).__name__}")
-                return  # Cannot determine transaction ID
-
-            # Try to pop the transaction from the bot's central store
-            if transaction_id is not None:  # type: ignore
-                transaction = self.bot.active_sentry_transactions.pop(transaction_id, None)
-
-            if transaction:
-                transaction.set_status(status)
-                transaction.finish()
-                logger.trace(
-                    f"Finished Sentry transaction ({status}) for errored {command_type} (ID: {transaction_id})",
-                )
-
-        except Exception as e:
-            logger.exception(f"Error during Sentry transaction finalization for ID {transaction_id}: {e}")
-            # Capture this specific failure to Sentry if needed
-            sentry_sdk.capture_exception(e, hint={"context": "Sentry transaction finalization"})
-
-    # --- Sentry Reporting Logic ---
-
-    @staticmethod
-    def _capture_exception_with_context(
-        error: Exception,
-        log_context: dict[str, Any],
-        level: str = "ERROR",
-        tags: dict[str, str] | None = None,
-    ) -> str | None:
-        """
-        Safely sends an exception to Sentry, enriching it with structured context.
-
-        This method pushes a new scope to Sentry, adds user information, the detailed
-        log context, the specified logging level, and any custom tags before capturing
-        the exception. It includes error handling to prevent Sentry SDK issues from
-        crashing the error handler itself.
-
-        Parameters
-        ----------
-        error : Exception
-            The exception to report.
-        log_context : dict[str, Any]
-            The dictionary of context information gathered by `_get_log_context`.
-        level : str, optional
-            The severity level for the Sentry event ('info', 'warning', 'error', etc.). Defaults to "ERROR".
-        tags : Optional[dict[str, str]], optional
-            Additional key-value tags to attach to the Sentry event. Defaults to None.
-
-        Returns
-        -------
-        Optional[str]
-            The Sentry event ID if capture was successful, otherwise None.
-        """
-        event_id: str | None = None
-        try:
-            # Create an isolated scope for this Sentry event.
-            with sentry_sdk.push_scope() as scope:
-                # Add user identification.
-                scope.set_user({"id": log_context.get("user_id"), "username": log_context.get("user_name")})
-                # Attach the detailed context dictionary under the 'discord' key.
-                scope.set_context("discord", log_context)
-                # Set the severity level of the event.
-                scope.level = level.lower()
-
-                # --- Add specific tags for better filtering/searching --- #
-                scope.set_tag("command_name", log_context.get("command_name", "Unknown"))
-                scope.set_tag("command_type", log_context.get("command_type", "Unknown"))
-                scope.set_tag("command_definition", log_context.get("command_definition", "Unknown"))
-
-                # Add new tag for interaction check
-                scope.set_tag("invoked_via_interaction", str(log_context.get("invoked_via_interaction", False)).lower())
-
-                # Handle potential None for guild_id (e.g., in DMs)
-                guild_id = log_context.get("guild_id")
-                scope.set_tag("guild_id", str(guild_id) if guild_id else "DM")
-
-                # Add any custom tags provided when calling this function.
-                if tags:
-                    for key, value in tags.items():
-                        scope.set_tag(key, value)
-
-                # Send the exception event to Sentry and capture the returned event ID.
-                event_id = sentry_sdk.capture_exception(error)
-
-                # Debug log indicating successful reporting.
-                if event_id:
-                    logger.debug(f"Reported {type(error).__name__} to Sentry ({event_id})")
-                else:
-                    logger.warning(f"Captured {type(error).__name__} but Sentry returned no ID.")
-
-        except Exception as sentry_exc:
-            # Log if reporting to Sentry fails, but don't let it stop the error handler.
-            logger.error(f"Failed to report {type(error).__name__} to Sentry: {sentry_exc}")
-
-        return event_id  # Return the event ID (or None if capture failed)
-
     def _log_and_report_error(
         self,
         root_error: Exception,
@@ -1057,16 +922,24 @@ def _log_and_report_error(
             logger.bind(**log_context).log(config.log_level, f"Handled expected error: {error_type.__name__}")
             if config.send_to_sentry:
                 # Optionally send handled errors to Sentry.
-                sentry_event_id = self._capture_exception_with_context(
+                sentry_event_id = self.bot.sentry_manager.capture_exception(
                     root_error,
-                    log_context,
-                    config.log_level,
+                    context=log_context,
+                    level=cast(LogLevelStr, config.log_level.lower()),
                     tags={"error_type": "handled"},
                 )
         else:
             # Log unhandled errors at ERROR level and always report to Sentry.
-            logger.bind(**log_context).error(f"Unhandled error: {error_type.__name__}")
-            sentry_event_id = self._log_and_capture_unhandled(root_error, log_context)
+            trace = traceback.format_exception(type(root_error), root_error, root_error.__traceback__)
+            formatted_trace = "".join(trace)
+            logger.bind(**log_context).error(f"Unhandled Error: {root_error}\nTraceback:\n{formatted_trace}")
+
+            sentry_event_id = self.bot.sentry_manager.capture_exception(
+                root_error,
+                context=log_context,
+                level="error",
+                tags={"error_type": "unhandled"},
+            )
         return sentry_event_id
 
     async def _try_edit_message_with_sentry_id(
@@ -1127,36 +1000,6 @@ async def _try_edit_message_with_sentry_id(
                 exc_info=unexpected_edit_exc,
             )
 
-    def _log_and_capture_unhandled(self, error: Exception, log_context: dict[str, Any]) -> str | None:
-        """
-        Handles errors not found in the `ERROR_CONFIG_MAP`.
-
-        It logs the error with its full traceback at the ERROR level and reports
-        it to Sentry, tagging it as 'unhandled'.
-
-        Parameters
-        ----------
-        error : Exception
-            The unhandled exception.
-        log_context : dict[str, Any]
-            The context dictionary for logging and reporting.
-
-        Returns
-        -------
-        Optional[str]
-            The Sentry event ID if capture was successful, otherwise None.
-        """
-        # Generate the formatted traceback string.
-        trace = traceback.format_exception(type(error), error, error.__traceback__)
-        formatted_trace = "".join(trace)
-
-        # Log the error locally with full traceback and context.
-        logger.bind(**log_context).error(f"Unhandled Error: {error}\nTraceback:\n{formatted_trace}")
-
-        # Report the unhandled error to Sentry with high severity.
-        # Directly return the result from _capture_exception_with_context.
-        return self._capture_exception_with_context(error, log_context, "ERROR", tags={"error_type": "unhandled"})
-
     # --- Command Suggestion Logic ---
 
     async def _suggest_command(self, ctx: commands.Context[Tux]) -> list[str] | None:
@@ -1197,7 +1040,7 @@ async def _suggest_command(self, ctx: commands.Context[Tux]) -> list[str] | None
         log_context["suggest_max_dist"] = max_distance
         log_context["suggest_max_count"] = max_suggestions
 
-        logger.bind(**log_context).debug("Attempting command suggestion.")
+        logger.bind(**log_context).trace("Attempting command suggestion.")
 
         # Store potential matches: {qualified_name: min_distance}
         command_distances: dict[str, int] = {}
@@ -1229,7 +1072,7 @@ async def _suggest_command(self, ctx: commands.Context[Tux]) -> list[str] | None
 
         # If no commands were within the distance threshold.
         if not command_distances:
-            logger.bind(**log_context).debug("No close command matches found for suggestion.")
+            logger.bind(**log_context).trace("No close command matches found for suggestion.")
             return None
 
         # Sort the found commands by distance (closest first).
@@ -1239,7 +1082,7 @@ async def _suggest_command(self, ctx: commands.Context[Tux]) -> list[str] | None
         final_suggestions = [cmd_name for cmd_name, _ in sorted_suggestions[:max_suggestions]]
 
         log_context["suggestions_found"] = final_suggestions
-        logger.bind(**log_context).debug("Command suggestions generated.")
+        logger.bind(**log_context).trace("Command suggestions generated.")
         # Return the list of names, or None if the list is empty (shouldn't happen here, but safety check).
         return final_suggestions or None
 
@@ -1277,7 +1120,7 @@ async def _handle_command_not_found(self, ctx: commands.Context[Tux]) -> None:
                 # Send the suggestion message, automatically deleting it after a short period.
                 await ctx.send(embed=embed, delete_after=SUGGESTION_DELETE_AFTER)
                 log_context["suggestions_sent"] = suggestions
-                logger.bind(**log_context).info("Sent command suggestions.")
+                logger.bind(**log_context).debug("Sent command suggestions.")
             except discord.HTTPException as e:
                 # Log if sending the suggestion message fails.
                 log_context["send_error"] = str(e)
@@ -1290,7 +1133,7 @@ async def _handle_command_not_found(self, ctx: commands.Context[Tux]) -> None:
         else:
             # Log that the command wasn't found and no suitable suggestions were generated.
             # No message is sent back to the user in this case to avoid unnecessary noise.
-            logger.bind(**log_context).info("Command not found, no suggestions generated.")
+            logger.bind(**log_context).debug("Command not found, no suggestions generated.")
 
     # --- Discord Event Listeners ---
 
diff --git a/tux/handlers/sentry.py b/tux/handlers/sentry.py
index cd849830d..9618fb597 100644
--- a/tux/handlers/sentry.py
+++ b/tux/handlers/sentry.py
@@ -6,6 +6,7 @@
 from loguru import logger
 
 from tux.bot import Tux
+from tux.utils.tracing import capture_span_exception, set_span_attributes, set_span_status
 
 # Type alias using PEP695 syntax
 type CommandObject = (
@@ -15,11 +16,12 @@
 
 class SentryHandler(commands.Cog):
     """
-    Handles Sentry transaction tracking for commands and interactions.
+    Handles Sentry error tracking and status management for commands and interactions.
 
-    This cog listens for Discord events to create and complete Sentry
-    transactions, providing performance monitoring and error context
-    for both prefix commands and slash commands.
+    This cog works with the automatic instrumentation from tracing.py to provide
+    proper error handling and status management for both prefix commands and slash commands.
+    It does not create transactions manually, as that is handled by the automatic
+    instrumentation system.
     """
 
     # Standard Sentry transaction statuses with ClassVar
@@ -57,155 +59,149 @@ def _is_sentry_available(self) -> bool:
         """
         return sentry_sdk.is_initialized()
 
-    def _create_transaction(
-        self,
-        operation: str,
-        name: str,
-        description: str,
-        tags: dict[str, Any],
-    ) -> Any | None:
-        """Create a Sentry transaction with the given parameters.
-
-        Parameters
-        ----------
-        operation : str
-            The operation type (e.g., "discord.command")
-        name : str
-            The name of the transaction
-        description : str
-            A description of the transaction
-        tags : dict[str, Any]
-            Tags to attach to the transaction
-
-        Returns
-        -------
-        Optional[Any]
-            The created transaction or None if Sentry is not initialized
-        """
-        if not self._is_sentry_available():
-            return None
-
-        try:
-            transaction = sentry_sdk.start_transaction(op=operation, name=name, description=description)
-
-            # Add all tags to the transaction
-            for key, value in tags.items():
-                transaction.set_tag(key, value)
-        except Exception as e:
-            logger.error(f"Error creating Sentry transaction: {e}")
-            sentry_sdk.capture_exception(e)
-            return None
-        else:
-            return transaction
-
-    def _finish_transaction(self, object_id: int, status: str = STATUS["OK"]) -> None:
-        """Finish a stored transaction with the given status.
+    def _set_command_context(self, ctx: commands.Context[Tux] | discord.Interaction, command_name: str) -> None:
+        """Set command context on the current Sentry span.
 
         Parameters
         ----------
-        object_id : int
-            The ID of the interaction or message
-        status : str
-            The status to set on the transaction
+        ctx : Union[commands.Context[Tux], discord.Interaction]
+            The command context or interaction
+        command_name : str
+            The name of the command being executed
         """
         if not self._is_sentry_available():
             return
 
-        if transaction := self.bot.active_sentry_transactions.pop(object_id, None):
-            transaction.set_status(status)
-            transaction.finish()
-            logger.trace(f"Finished Sentry transaction ({status}) for {transaction.name}")
+        # Set command-specific tags
+        if isinstance(ctx, commands.Context):
+            set_span_attributes(
+                {
+                    "discord.command.name": command_name,
+                    "discord.guild.id": str(ctx.guild.id) if ctx.guild else "DM",
+                    "discord.channel.id": ctx.channel.id,
+                    "discord.user.id": ctx.author.id,
+                    "discord.message.id": ctx.message.id,
+                    "discord.command.type": "prefix",
+                },
+            )
+        else:  # discord.Interaction
+            set_span_attributes(
+                {
+                    "discord.command.name": command_name,
+                    "discord.guild.id": str(ctx.guild_id) if ctx.guild_id else "DM",
+                    "discord.channel.id": ctx.channel_id,
+                    "discord.user.id": ctx.user.id,
+                    "discord.interaction.id": ctx.id,
+                    "discord.interaction.type": ctx.type.name,
+                    "discord.command.type": "slash",
+                },
+            )
 
     @commands.Cog.listener()
     async def on_command(self, ctx: commands.Context[Tux]) -> None:
         """
-        Start a Sentry transaction for a prefix command.
+        Set context for a prefix command execution.
+
+        This works with the automatic instrumentation to add command-specific
+        context to the existing transaction.
 
         Parameters
         ----------
         ctx : commands.Context[Tux]
             The command context
         """
-        if not self._is_sentry_available():
-            return
-
         if command_name := (ctx.command.qualified_name if ctx.command else "Unknown Command"):
-            tags = {
-                "discord.command.name": command_name,
-                "discord.guild.id": str(ctx.guild.id) if ctx.guild else "DM",
-                "discord.channel.id": ctx.channel.id,
-                "discord.user.id": ctx.author.id,
-                "discord.message.id": ctx.message.id,
-                "discord.command.type": "prefix",
-            }
-
-            if transaction := self._create_transaction(
-                operation="discord.command",
-                name=command_name,
-                description=ctx.message.content,
-                tags=tags,
-            ):
-                self.bot.active_sentry_transactions[ctx.message.id] = transaction
-                logger.trace(f"Started transaction for prefix command: {command_name}")
+            self._set_command_context(ctx, command_name)
+            logger.trace(f"Set context for prefix command: {command_name}")
 
     @commands.Cog.listener()
-    async def on_command_completion(self, ctx: commands.Context[Tux]) -> None:
+    async def on_command_error(self, ctx: commands.Context[Tux], error: commands.CommandError) -> None:
         """
-        Finish the Sentry transaction for a completed prefix command.
+        Handle errors for prefix commands.
+
+        This captures command errors and sets the appropriate status on the
+        current transaction.
 
         Parameters
         ----------
         ctx : commands.Context[Tux]
             The command context
+        error : commands.CommandError
+            The error that occurred
         """
-        self._finish_transaction(ctx.message.id, self.STATUS["OK"])
+        if not self._is_sentry_available():
+            return
+
+        # Capture the error in the current span
+        capture_span_exception(error, command_name=ctx.command.qualified_name if ctx.command else "Unknown")
+
+        # Set appropriate status based on error type
+        if isinstance(error, commands.CommandNotFound):
+            set_span_status("NOT_FOUND")
+        elif isinstance(error, commands.MissingPermissions):
+            set_span_status("PERMISSION_DENIED")
+        elif isinstance(error, commands.BadArgument):
+            set_span_status("INVALID_ARGUMENT")
+        else:
+            set_span_status("ERROR")
+
+        logger.debug(f"Captured error for prefix command: {error}")
 
     @commands.Cog.listener()
     async def on_interaction(self, interaction: discord.Interaction) -> None:
         """
-        Start a Sentry transaction for application command interactions.
+        Set context for application command interactions.
+
+        This works with the automatic instrumentation to add command-specific
+        context to the existing transaction.
 
         Parameters
         ----------
         interaction : discord.Interaction
             The interaction object
         """
-        if not self._is_sentry_available() or interaction.type != discord.InteractionType.application_command:
+        if interaction.type != discord.InteractionType.application_command:
             return
 
         if command_name := (interaction.command.qualified_name if interaction.command else "Unknown App Command"):
-            tags = {
-                "discord.command.name": command_name,
-                "discord.guild.id": str(interaction.guild_id) if interaction.guild_id else "DM",
-                "discord.channel.id": interaction.channel_id,
-                "discord.user.id": interaction.user.id,
-                "discord.interaction.id": interaction.id,
-                "discord.interaction.type": interaction.type.name,
-                "discord.command.type": "slash",
-            }
-
-            if transaction := self._create_transaction(
-                operation="discord.app_command",
-                name=command_name,
-                description=f"/{command_name}",
-                tags=tags,
-            ):
-                self.bot.active_sentry_transactions[interaction.id] = transaction
-                logger.trace(f"Started transaction for app command: {command_name}")
+            self._set_command_context(interaction, command_name)
+            logger.trace(f"Set context for app command: {command_name}")
 
     @commands.Cog.listener()
-    async def on_app_command_completion(self, interaction: discord.Interaction, command: CommandObject) -> None:
+    async def on_app_command_error(
+        self,
+        interaction: discord.Interaction,
+        error: discord.app_commands.AppCommandError,
+    ) -> None:
         """
-        Finish the Sentry transaction for a completed application command.
+        Handle errors for application commands.
+
+        This captures command errors and sets the appropriate status on the
+        current transaction.
 
         Parameters
         ----------
         interaction : discord.Interaction
             The interaction object
-        command : CommandObject
-            The command that was completed
+        error : discord.app_commands.AppCommandError
+            The error that occurred
         """
-        self._finish_transaction(interaction.id, self.STATUS["OK"])
+        if not self._is_sentry_available():
+            return
+
+        # Capture the error in the current span
+        command_name = interaction.command.qualified_name if interaction.command else "Unknown"
+        capture_span_exception(error, command_name=command_name)
+
+        # Set appropriate status based on error type
+        if isinstance(error, discord.app_commands.CommandNotFound):
+            set_span_status("NOT_FOUND")
+        elif isinstance(error, discord.app_commands.MissingPermissions):
+            set_span_status("PERMISSION_DENIED")
+        else:
+            set_span_status("ERROR")
+
+        logger.debug(f"Captured error for app command: {error}")
 
 
 async def setup(bot: Tux) -> None:
diff --git a/tux/utils/banner.py b/tux/utils/banner.py
index 4cfe6c220..a0cc60126 100644
--- a/tux/utils/banner.py
+++ b/tux/utils/banner.py
@@ -1,6 +1,7 @@
 """Banner creation and formatting utilities for Tux."""
 
 from dataclasses import dataclass, field
+from datetime import UTC, datetime
 from typing import NamedTuple
 
 from rich.console import Console
@@ -72,13 +73,13 @@ def _create_banner_table(self) -> Table:
         mode_text = "Development" if self.config.dev_mode else "Production"
 
         info_data = [
-            ("", ""),  # Empty row to shift content down
-            ("Bot Name", f"{self.config.bot_name} (Tux)"),
+            ("Bot Name", f"{self.config.bot_name}"),
             ("Version", self.config.version),
             ("Bot ID", str(self.config.bot_id or "Unknown")),
             ("Status", f"Watching {self.config.guild_count} servers with {self.config.user_count} users"),
             ("Prefix", self.config.prefix),
             ("Mode", Text(mode_text, style=mode_style)),
+            ("Date", datetime.now(UTC).strftime("%Y-%m-%d %H:%M:%S")),
         ]
 
         # Add rows, combining ASCII art with info
diff --git a/tux/utils/context_utils.py b/tux/utils/context_utils.py
new file mode 100644
index 000000000..5620099d1
--- /dev/null
+++ b/tux/utils/context_utils.py
@@ -0,0 +1,108 @@
+"""
+Command and Interaction Context Utilities.
+
+This module provides helper functions to abstract and normalize the process of
+extracting contextual information from different types of command invocations
+in `discord.py`.
+
+The primary goal is to create a single, consistent dictionary format for context
+data, regardless of whether the command was triggered by a traditional prefix
+command (`commands.Context`) or a slash command (`discord.Interaction`).
+This standardized context is invaluable for logging, error reporting (e.g., to
+Sentry), and any other system that needs to operate on command data without
+worrying about the source type.
+"""
+
+from __future__ import annotations
+
+from typing import Any
+
+from discord import Interaction
+from discord.ext import commands
+
+# Type alias for a command context or an interaction.
+ContextOrInteraction = commands.Context[Any] | Interaction
+
+
+def _get_interaction_details(source: Interaction) -> dict[str, Any]:
+    """
+    Extracts context details specifically from a discord.Interaction.
+
+    Parameters
+    ----------
+    source : Interaction
+        The interaction object from a slash command.
+
+    Returns
+    -------
+    dict[str, Any]
+        A dictionary containing interaction-specific context.
+    """
+    details: dict[str, Any] = {
+        "command_type": "slash",
+        "interaction_id": source.id,
+        "channel_id": source.channel_id,
+        "guild_id": source.guild_id,
+    }
+    if source.command:
+        details["command_name"] = source.command.qualified_name
+    return details
+
+
+def _get_context_details(source: commands.Context[Any]) -> dict[str, Any]:
+    """
+    Extracts context details specifically from a commands.Context.
+
+    Parameters
+    ----------
+    source : commands.Context[Any]
+        The context object from a prefix command.
+
+    Returns
+    -------
+    dict[str, Any]
+        A dictionary containing context-specific data.
+    """
+    details: dict[str, Any] = {
+        "command_type": "prefix",
+        "message_id": source.message.id,
+        "channel_id": source.channel.id,
+        "guild_id": source.guild.id if source.guild else None,
+    }
+    if source.command:
+        details["command_name"] = source.command.qualified_name
+        details["command_prefix"] = source.prefix
+        details["command_invoked_with"] = source.invoked_with
+    return details
+
+
+def get_interaction_context(source: ContextOrInteraction) -> dict[str, Any]:
+    """
+    Builds a standardized dictionary of context from a command or interaction.
+
+    This is the main public function of the module. It takes either a
+    `commands.Context` or a `discord.Interaction` and returns a dictionary
+    with a consistent set of keys, abstracting away the differences between
+    the two source types.
+
+    Args:
+        source: The command `Context` or `Interaction` object.
+
+    Returns:
+        A dictionary with standardized context keys like `user_id`,
+        `command_name`, `guild_id`, `command_type`, etc.
+    """
+    user = source.user if isinstance(source, Interaction) else source.author
+
+    # Base context is common to both types
+    context: dict[str, Any] = {
+        "user_id": user.id,
+        "user_name": str(user),
+        "is_interaction": isinstance(source, Interaction),
+    }
+
+    # Delegate to helper functions for type-specific details
+    details = _get_interaction_details(source) if isinstance(source, Interaction) else _get_context_details(source)
+    context |= details
+
+    return context
diff --git a/tux/utils/emoji.py b/tux/utils/emoji_manager.py
similarity index 100%
rename from tux/utils/emoji.py
rename to tux/utils/emoji_manager.py
diff --git a/tux/utils/hot_reload.py b/tux/utils/hot_reload.py
index 4a09670e7..a113a28ba 100644
--- a/tux/utils/hot_reload.py
+++ b/tux/utils/hot_reload.py
@@ -5,6 +5,8 @@
 with comprehensive error handling and performance monitoring.
 """
 
+from __future__ import annotations
+
 import ast
 import asyncio
 import hashlib
@@ -14,37 +16,24 @@
 import sys
 import time
 from abc import ABC, abstractmethod
-from collections.abc import Callable, Mapping, Sequence
+from collections.abc import Callable, Sequence
 from contextlib import contextmanager, suppress
 from dataclasses import dataclass, field
 from pathlib import Path
-from types import ModuleType
 from typing import Any, Protocol, TypeVar, cast
 
-import sentry_sdk
 import watchdog.events
 import watchdog.observers
 from discord.ext import commands
 from loguru import logger
 
-from tux.utils.sentry import span
+from tux.utils.protocols import BotProtocol
+from tux.utils.tracing import span
 
 # Type variables and protocols
 F = TypeVar("F", bound=Callable[..., Any])
 
 
-class BotProtocol(Protocol):
-    """Protocol for bot-like objects."""
-
-    @property
-    def extensions(self) -> Mapping[str, ModuleType]: ...
-
-    help_command: Any
-
-    async def load_extension(self, name: str) -> None: ...
-    async def reload_extension(self, name: str) -> None: ...
-
-
 class FileSystemWatcherProtocol(Protocol):
     """Protocol for file system watchers."""
 
@@ -260,9 +249,8 @@ def reload_module_by_name(module_name: str) -> bool:
             importlib.reload(sys.modules[module_name])
     except Exception as e:
         logger.error(f"Failed to reload module {module_name}: {e}")
-        if sentry_sdk.is_initialized():
-            sentry_sdk.capture_exception(e)
-        return False
+        # No sentry_manager available here, so no Sentry capture
+        raise
     else:
         logger.debug(f"Reloaded module {module_name}")
         return True
@@ -382,9 +370,8 @@ def scan_class_definitions(self, file_path: Path, module_name: str) -> dict[str,
 
         except Exception as e:
             logger.debug(f"Error scanning class definitions in {file_path}: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
-            return {}
+            # No sentry_manager available here, so no Sentry capture
+            raise
         else:
             return classes
 
@@ -458,9 +445,8 @@ def scan_dependencies(self, file_path: Path) -> set[str]:
 
         except Exception as e:
             logger.debug(f"Error scanning dependencies in {file_path}: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
-            return set()
+            # No sentry_manager available here, so no Sentry capture
+            raise
         else:
             return dependencies
 
@@ -698,9 +684,8 @@ def hot_patch_class(self, module_name: str, class_name: str, new_class: type) ->
             setattr(module, class_name, new_class)
         except Exception as e:
             logger.error(f"Failed to hot patch class {class_name} in {module_name}: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
-            return False
+            # No sentry_manager available here, so no Sentry capture
+            raise
         else:
             logger.info(f"Hot patched class {class_name} in {module_name}")
             return True
@@ -717,30 +702,48 @@ def cleanup_context(self):
 
 
 class CogWatcher(watchdog.events.FileSystemEventHandler):
-    """Enhanced cog watcher with smart dependency tracking and improved error handling."""
-
-    def __init__(self, bot: BotProtocol, path: str, *, recursive: bool = True, config: HotReloadConfig | None = None):
-        """Initialize the cog watcher with validation."""
-        self._config = config or HotReloadConfig()
-        validate_config(self._config)
+    """
+    Watches for file changes and automatically reloads affected cogs.
 
-        watch_path = Path(path)
-        if not watch_path.exists():
-            msg = f"Watch path does not exist: {path}"
-            raise FileWatchError(msg)
+    This class extends watchdog's FileSystemEventHandler to monitor Python files
+    in the bot's directory and trigger automatic reloading when changes are detected.
+    """
 
+    def __init__(
+        self,
+        bot: commands.Bot | BotProtocol,
+        path: str,
+        *,
+        recursive: bool = True,
+        config: HotReloadConfig | None = None,
+    ):
+        """
+        Initialize the cog watcher.
+
+        Parameters
+        ----------
+        bot : commands.Bot | BotProtocol
+            The bot instance to reload extensions on.
+        path : str
+            The directory path to watch for changes.
+        recursive : bool, optional
+            Whether to watch subdirectories recursively, by default True
+        config : HotReloadConfig | None, optional
+            Configuration for the hot reload system, by default None
+        """
+        super().__init__()
         self.bot = bot
-        self.path = str(watch_path.resolve())
+        self.watch_path = Path(path)
         self.recursive = recursive
+        self.config = config or HotReloadConfig()
+        validate_config(self.config)
+        self.extension_map: dict[str, str] = {}
+        self.dependency_graph = DependencyGraph(self.config)
+        self.file_hash_tracker = FileHashTracker()
+        self.class_tracker = ClassDefinitionTracker()
+        self.debounce_timers: dict[str, asyncio.TimerHandle] = {}
         self.observer = watchdog.observers.Observer()
-        self.observer.schedule(self, self.path, recursive=recursive)
-        self.base_dir = Path(__file__).parent.parent
-
-        # Store a relative path for logging
-        try:
-            self.display_path = str(Path(path).relative_to(self.base_dir.parent))
-        except ValueError:
-            self.display_path = path
+        self.pending_tasks: list[asyncio.Task[None]] = []
 
         # Store the main event loop from the calling thread
         try:
@@ -749,23 +752,15 @@ def __init__(self, bot: BotProtocol, path: str, *, recursive: bool = True, confi
             msg = "Hot reload must be initialized from within an async context"
             raise HotReloadError(msg) from e
 
-        # Track special files
+        # Set up base directory and help file path
+        self.base_dir = Path(__file__).parent.parent
         self.help_file_path = self.base_dir / "help.py"
 
-        # Extension tracking
-        self.path_to_extension: dict[str, str] = {}
-        self.pending_tasks: list[asyncio.Task[None]] = []
-
-        # Enhanced dependency tracking
-        self.dependency_graph = DependencyGraph(self._config)
-
-        # Debouncing configuration
-        self._debounce_timers: dict[str, asyncio.Handle] = {}
-
-        # Build initial extension map
+        # Build the extension map and populate file hashes
         self._build_extension_map()
-
-        logger.debug(f"CogWatcher initialized for path: {self.display_path}")
+        if self.config.prepopulate_hashes:
+            cached_count = self._populate_all_file_hashes()
+            logger.debug(f"Pre-populated {cached_count} file hashes")
 
     @span("watcher.build_extension_map")
     def _build_extension_map(self) -> None:
@@ -779,15 +774,15 @@ def _build_extension_map(self) -> None:
             try:
                 path = path_from_extension(extension)
                 if path.exists():
-                    self.path_to_extension[str(path)] = extension
+                    self.extension_map[str(path)] = extension
                     self.dependency_graph.update_dependencies(path, extension)
                     extension_count += 1
                 else:
                     logger.warning(f"Could not find file for extension {extension}, expected at {path}")
             except Exception as e:
                 logger.error(f"Error processing extension {extension}: {e}")
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
+                # No sentry_manager available here, so no Sentry capture
+                raise
 
         # Pre-populate hash cache for all Python files in watched directories
         # This eliminates "first encounter" issues for any file
@@ -802,16 +797,16 @@ def _populate_all_file_hashes(self) -> int:
         Pre-populate hash cache for all files in watched directories matching configured extensions.
         This can be disabled via configuration to avoid startup overhead.
         """
-        if not self._config.prepopulate_hashes:
+        if not self.config.prepopulate_hashes:
             logger.debug("Hash pre-population disabled in configuration")
             return 0
 
         cached_count = 0
 
         # Get the root watch path (this includes the entire tux directory)
-        watch_root = Path(self.path)
+        watch_root = Path(self.watch_path)
 
-        for ext in self._config.hash_extensions:
+        for ext in self.config.hash_extensions:
             for file_path in watch_root.rglob(f"*{ext}"):
                 try:
                     # Pre-populate cache silently using the public method
@@ -819,14 +814,17 @@ def _populate_all_file_hashes(self) -> int:
                     cached_count += 1
                 except Exception as e:
                     logger.warning(f"Failed to hash {file_path}: {e}")
+                    # No sentry_manager available here, so no Sentry capture
+                    raise
 
         return cached_count
 
     def start(self) -> None:
         """Start watching for file changes."""
         try:
+            self.observer.schedule(self, str(self.watch_path), recursive=self.recursive)
             self.observer.start()
-            logger.info(f"Hot reload watching {self.display_path}")
+            logger.info(f"Hot reload watching {self.watch_path}")
         except Exception as e:
             msg = f"Failed to start file watcher: {e}"
             raise FileWatchError(msg) from e
@@ -847,9 +845,9 @@ def stop(self) -> None:
                 task.cancel()
 
         # Cancel debounce timers
-        for timer in self._debounce_timers.values():
+        for timer in self.debounce_timers.values():
             timer.cancel()
-        self._debounce_timers.clear()
+        self.debounce_timers.clear()
 
         logger.info("Stopped watching for changes")
 
@@ -875,13 +873,13 @@ def on_modified(self, event: watchdog.events.FileSystemEvent) -> None:
         file_key = str(file_path)
 
         # Cancel existing debounce timer if any
-        if file_key in self._debounce_timers:
-            self._debounce_timers[file_key].cancel()
+        if file_key in self.debounce_timers:
+            self.debounce_timers[file_key].cancel()
 
         # Set new debounce timer
         try:
-            self._debounce_timers[file_key] = self.loop.call_later(
-                self._config.debounce_delay,
+            self.debounce_timers[file_key] = self.loop.call_later(
+                self.config.debounce_delay,
                 self._handle_file_change_debounced,
                 file_path,
             )
@@ -901,11 +899,11 @@ def _handle_file_change_debounced(self, file_path: Path) -> None:
         file_key = str(file_path)
 
         # Remove from debounce tracking
-        if file_key in self._debounce_timers:
-            del self._debounce_timers[file_key]
+        if file_key in self.debounce_timers:
+            del self.debounce_timers[file_key]
 
         # Validate syntax before attempting reload (if enabled)
-        if self._config.validate_syntax and file_path.suffix == ".py" and not validate_python_syntax(file_path):
+        if self.config.validate_syntax and file_path.suffix == ".py" and not validate_python_syntax(file_path):
             logger.debug(f"Skipping hot reload for {file_path.name} due to syntax errors")
             return
 
@@ -918,8 +916,8 @@ def _handle_file_change_debounced(self, file_path: Path) -> None:
             self._handle_extension_file(file_path)
         except Exception as e:
             logger.error(f"Error handling file change for {file_path}: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
+            # No sentry_manager available here, so no Sentry capture
+            raise
 
     def _handle_special_files(self, file_path: Path) -> bool:
         """Handle special files like help.py and __init__.py."""
@@ -943,7 +941,7 @@ def _handle_extension_file(self, file_path: Path) -> None:
             self.dependency_graph.update_dependencies(file_path, module_name)
 
         # Check direct mapping first
-        if extension := self.path_to_extension.get(str(file_path)):
+        if extension := self.extension_map.get(str(file_path)):
             self._reload_extension(extension)
             return
 
@@ -1014,7 +1012,7 @@ def _process_extension_reload(self, extension: str, file_path: Path | None = Non
         self._reload_extension(extension)
 
         if file_path:
-            self.path_to_extension[str(file_path)] = extension
+            self.extension_map[str(file_path)] = extension
 
     @span("watcher.try_reload_variations")
     def _try_reload_extension_variations(self, extension: str, file_path: Path) -> bool:
@@ -1030,7 +1028,7 @@ def _try_reload_extension_variations(self, extension: str, file_path: Path) -> b
             shorter_ext = ".".join(parts[:i])
             if shorter_ext in self.bot.extensions:
                 logger.warning(f"Skipping reload of {extension} as parent module {shorter_ext} already loaded")
-                self.path_to_extension[str(file_path)] = shorter_ext
+                self.extension_map[str(file_path)] = shorter_ext
                 return True
 
         # Check parent modules
@@ -1074,8 +1072,8 @@ def _handle_init_file_change(self, init_file_path: Path) -> None:
                     self._process_extension_reload(ext)
         except Exception as e:
             logger.error(f"Error handling __init__.py change for {init_file_path}: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
+            # No sentry_manager available here, so no Sentry capture
+            raise
 
     def _collect_extensions_to_reload(self, full_package: str, short_package: str) -> list[str]:
         """Collect extensions that need to be reloaded based on package names."""
@@ -1098,8 +1096,8 @@ def _reload_extension(self, extension: str) -> None:
             asyncio.run_coroutine_threadsafe(self._async_reload_extension(extension), self.loop)
         except Exception as e:
             logger.error(f"Failed to schedule reload of extension {extension}: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
+            # No sentry_manager available here, so no Sentry capture
+            raise
 
     def _reload_help(self) -> None:
         """Reload the help command with proper error handling."""
@@ -1108,8 +1106,8 @@ def _reload_help(self) -> None:
             asyncio.run_coroutine_threadsafe(self._async_reload_help(), self.loop)
         except Exception as e:
             logger.error(f"Failed to schedule reload of help command: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
+            # No sentry_manager available here, so no Sentry capture
+            raise
 
     @span("reload.extension")
     async def _async_reload_extension(self, extension: str) -> None:
@@ -1162,12 +1160,13 @@ async def _handle_extension_not_loaded(self, extension: str) -> None:
 
             # Update our mapping
             path = path_from_extension(extension)
-            self.path_to_extension[str(path)] = extension
+            self.extension_map[str(path)] = extension
         except commands.ExtensionError as e:
             logger.error(f"❌ Failed to load new extension {extension}: {e}")
-            # Only send to Sentry if it's not a common development error
-            if sentry_sdk.is_initialized() and not self._is_development_error(e):
-                sentry_sdk.capture_exception(e)
+            # Only send to Sentry if it's not a common development error and bot supports it
+            if not self._is_development_error(e) and isinstance(self.bot, BotProtocol):
+                self.bot.sentry_manager.capture_exception(e)
+            raise
 
     async def _reload_extension_core(self, extension: str) -> None:
         """Core extension reloading logic."""
@@ -1178,9 +1177,9 @@ async def _reload_extension_core(self, extension: str) -> None:
             raise
         except commands.ExtensionError as e:
             logger.error(f"❌ Failed to reload extension {extension}: {e}")
-            # Only send to Sentry if it's not a common development error
-            if sentry_sdk.is_initialized() and not self._is_development_error(e):
-                sentry_sdk.capture_exception(e)
+            # Only send to Sentry if it's not a common development error and bot supports it
+            if not self._is_development_error(e) and isinstance(self.bot, BotProtocol):
+                self.bot.sentry_manager.capture_exception(e)
             raise
 
     @span("reload.help")
@@ -1203,12 +1202,12 @@ async def _async_reload_help(self) -> None:
                 logger.info("✅ Reloaded help command")
             except (AttributeError, ImportError) as e:
                 logger.error(f"Error accessing TuxHelp class: {e}")
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
+                # No sentry_manager available here, so no Sentry capture
+                raise
         except Exception as e:
             logger.error(f"❌ Failed to reload help command: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
+            # No sentry_manager available here, so no Sentry capture
+            raise
 
     @span("reload.flag_dependent_cogs")
     def _reload_flag_class_dependent_cogs(self) -> None:
@@ -1414,8 +1413,8 @@ async def wrapper(self: Any, *args: Any, **kwargs: Any) -> Any:
                 logger.info("🔥 Hot reload active")
             except Exception as e:
                 logger.error(f"Failed to start hot reload system: {e}")
-                if sentry_sdk.is_initialized():
-                    sentry_sdk.capture_exception(e)
+                # No sentry_manager available here, so no Sentry capture
+                raise
 
             return result
 
@@ -1463,9 +1462,8 @@ def auto_discover_cogs(path: str = "cogs") -> list[str]:
                 continue
     except Exception as e:
         logger.error(f"Error during cog discovery: {e}")
-        if sentry_sdk.is_initialized():
-            sentry_sdk.capture_exception(e)
-        return []
+        # No sentry_manager available here, so no Sentry capture
+        raise
     else:
         return sorted(discovered)
 
@@ -1473,7 +1471,7 @@ def auto_discover_cogs(path: str = "cogs") -> list[str]:
 class HotReload(commands.Cog):
     """Hot reload cog for backward compatibility and direct usage."""
 
-    def __init__(self, bot: commands.Bot) -> None:
+    def __init__(self, bot: commands.Bot | BotProtocol) -> None:
         self.bot = bot
 
         logger.debug(f"Initializing HotReload cog with {len(bot.extensions)} loaded extensions")
@@ -1485,8 +1483,9 @@ def __init__(self, bot: commands.Bot) -> None:
             self.watcher.start()
         except Exception as e:
             logger.error(f"Failed to initialize hot reload watcher: {e}")
-            if sentry_sdk.is_initialized():
-                sentry_sdk.capture_exception(e)
+            # Type-safe access to sentry_manager
+            if isinstance(bot, BotProtocol):
+                bot.sentry_manager.capture_exception(e)
             raise
 
     async def cog_unload(self) -> None:
@@ -1499,7 +1498,7 @@ async def cog_unload(self) -> None:
             logger.error(f"Error during HotReload cog unload: {e}")
 
 
-async def setup(bot: commands.Bot) -> None:
+async def setup(bot: commands.Bot | BotProtocol) -> None:
     """Set up the hot reload cog."""
     logger.info("Setting up hot reloader")
     logger.debug(f"Bot has {len(bot.extensions)} extensions loaded")
@@ -1511,11 +1510,11 @@ async def setup(bot: commands.Bot) -> None:
             logger.warning(f"  - {issue}")
 
     try:
+        # The actual bot instance will have the required attributes
         await bot.add_cog(HotReload(bot))
     except Exception as e:
         logger.error(f"Failed to setup hot reload cog: {e}")
-        if sentry_sdk.is_initialized():
-            sentry_sdk.capture_exception(e)
+        # No sentry_manager available here, so no Sentry capture
         raise
 
 
diff --git a/tux/utils/protocols.py b/tux/utils/protocols.py
new file mode 100644
index 000000000..9499d3a6d
--- /dev/null
+++ b/tux/utils/protocols.py
@@ -0,0 +1,43 @@
+"""
+Defines structural type hints (Protocols) for dependency injection.
+
+This module contains Protocol classes that define the structure of objects
+required by different parts of the application. By using these protocols
+for type hinting instead of concrete classes (like `Tux`), we can achieve
+loose coupling between components.
+
+This approach, known as structural subtyping or static duck typing, allows
+any object that has the required attributes and methods to be used,
+breaking circular import dependencies and making the codebase more modular
+and easier to test.
+"""
+
+from __future__ import annotations
+
+from collections.abc import Mapping
+from types import ModuleType
+from typing import TYPE_CHECKING, Any, Protocol, runtime_checkable
+
+if TYPE_CHECKING:
+    from discord.ext import commands
+
+    from tux.utils.sentry_manager import SentryManager
+
+
+@runtime_checkable
+class BotProtocol(Protocol):
+    """A protocol for the bot instance to provide necessary attributes."""
+
+    @property
+    def cogs(self) -> Mapping[str, commands.Cog]: ...
+
+    @property
+    def extensions(self) -> Mapping[str, ModuleType]: ...
+
+    help_command: Any
+
+    sentry_manager: SentryManager
+
+    async def load_extension(self, name: str) -> None: ...
+    async def reload_extension(self, name: str) -> None: ...
+    async def add_cog(self, cog: commands.Cog, /, *, override: bool = False) -> None: ...
diff --git a/tux/utils/sentry.py b/tux/utils/sentry.py
deleted file mode 100644
index 1108b9825..000000000
--- a/tux/utils/sentry.py
+++ /dev/null
@@ -1,291 +0,0 @@
-"""
-Sentry instrumentation utilities for tracing and performance monitoring.
-
-This module provides decorators and context managers for instrumenting
-code with Sentry transactions and spans, simplifying the addition of
-performance monitoring and error tracking.
-"""
-
-import asyncio
-import functools
-import time
-import traceback
-from collections.abc import Callable, Generator
-from contextlib import contextmanager
-from typing import Any, ParamSpec, TypeVar, cast
-
-import sentry_sdk
-
-# Type variables for better type hints with generic functions
-P = ParamSpec("P")
-T = TypeVar("T")
-R = TypeVar("R")
-
-
-class DummySpan:
-    """A dummy span object for when Sentry is not initialized."""
-
-    def set_tag(self, *args: Any, **kwargs: Any) -> "DummySpan":
-        return self
-
-    def set_data(self, *args: Any, **kwargs: Any) -> "DummySpan":
-        return self
-
-    def set_status(self, *args: Any, **kwargs: Any) -> "DummySpan":
-        return self
-
-    def set_name(self, name: str) -> "DummySpan":
-        return self
-
-
-class DummyTransaction(DummySpan):
-    """A dummy transaction object for when Sentry is not initialized."""
-
-
-def safe_set_name(obj: Any, name: str) -> None:
-    """
-    Safely set the name on a span or transaction object.
-
-    Parameters
-    ----------
-    obj : Any
-        The span or transaction object
-    name : str
-        The name to set
-    """
-    if hasattr(obj, "set_name"):
-        # Use getattr to avoid static type checking issues
-        set_name_func = obj.set_name
-        set_name_func(name)
-
-
-def transaction(
-    op: str,
-    name: str | None = None,
-    description: str | None = None,
-) -> Callable[[Callable[P, R]], Callable[P, R]]:
-    """
-    Decorator to wrap a function with a Sentry transaction.
-
-    Parameters
-    ----------
-    op : str
-        The operation name for the transaction.
-    name : Optional[str]
-        The name for the transaction. Defaults to the function name.
-    description : Optional[str]
-        A description of what the transaction is doing.
-
-    Returns
-    -------
-    Callable
-        The decorated function.
-    """
-
-    def decorator(func: Callable[P, R]) -> Callable[P, R]:
-        if asyncio.iscoroutinefunction(func):
-
-            @functools.wraps(func)
-            async def async_transaction_wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
-                transaction_name = name or f"{func.__module__}.{func.__qualname__}"
-                start_time = time.perf_counter()
-
-                if not sentry_sdk.is_initialized():
-                    return await func(*args, **kwargs)
-
-                with sentry_sdk.start_transaction(
-                    op=op,
-                    name=transaction_name,
-                    description=description or f"Executing {func.__qualname__}",
-                ) as transaction_obj:
-                    try:
-                        result = await func(*args, **kwargs)
-                    except Exception as e:
-                        transaction_obj.set_status("internal_error")
-                        transaction_obj.set_data("error", str(e))
-                        transaction_obj.set_data("traceback", traceback.format_exc())
-                        raise
-                    else:
-                        transaction_obj.set_status("ok")
-                        return result
-                    finally:
-                        transaction_obj.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
-
-            return cast(Callable[P, R], async_transaction_wrapper)
-
-        @functools.wraps(func)
-        def sync_transaction_wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
-            transaction_name = name or f"{func.__module__}.{func.__qualname__}"
-            start_time = time.perf_counter()
-
-            if not sentry_sdk.is_initialized():
-                return func(*args, **kwargs)
-
-            with sentry_sdk.start_transaction(
-                op=op,
-                name=transaction_name,
-                description=description or f"Executing {func.__qualname__}",
-            ) as transaction_obj:
-                try:
-                    result = func(*args, **kwargs)
-                except Exception as e:
-                    transaction_obj.set_status("internal_error")
-                    transaction_obj.set_data("error", str(e))
-                    transaction_obj.set_data("traceback", traceback.format_exc())
-                    raise
-                else:
-                    transaction_obj.set_status("ok")
-                    return result
-                finally:
-                    transaction_obj.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
-
-        return sync_transaction_wrapper
-
-    return decorator
-
-
-def span(op: str, description: str | None = None) -> Callable[[Callable[P, R]], Callable[P, R]]:
-    """
-    Decorator to wrap a function with a Sentry span.
-
-    Parameters
-    ----------
-    op : str
-        The operation name for the span.
-    description : Optional[str]
-        A description of what the span is doing.
-
-    Returns
-    -------
-    Callable
-        The decorated function.
-    """
-
-    def decorator(func: Callable[P, R]) -> Callable[P, R]:
-        if asyncio.iscoroutinefunction(func):
-
-            @functools.wraps(func)
-            async def async_span_wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
-                span_description = description or f"Executing {func.__qualname__}"
-                start_time = time.perf_counter()
-
-                if not sentry_sdk.is_initialized():
-                    return await func(*args, **kwargs)
-
-                with sentry_sdk.start_span(op=op, description=span_description) as span_obj:
-                    try:
-                        # Use the helper function to safely set name if available
-                        safe_set_name(span_obj, func.__qualname__)
-
-                        result = await func(*args, **kwargs)
-                    except Exception as e:
-                        span_obj.set_status("internal_error")
-                        span_obj.set_data("error", str(e))
-                        span_obj.set_data("traceback", traceback.format_exc())
-                        raise
-                    else:
-                        span_obj.set_status("ok")
-                        return result
-                    finally:
-                        span_obj.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
-
-            return cast(Callable[P, R], async_span_wrapper)
-
-        @functools.wraps(func)
-        def sync_span_wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
-            span_description = description or f"Executing {func.__qualname__}"
-            start_time = time.perf_counter()
-
-            if not sentry_sdk.is_initialized():
-                return func(*args, **kwargs)
-
-            with sentry_sdk.start_span(op=op, description=span_description) as span_obj:
-                try:
-                    # Use the helper function to safely set name if available
-                    safe_set_name(span_obj, func.__qualname__)
-
-                    result = func(*args, **kwargs)
-                except Exception as e:
-                    span_obj.set_status("internal_error")
-                    span_obj.set_data("error", str(e))
-                    span_obj.set_data("traceback", traceback.format_exc())
-                    raise
-                else:
-                    span_obj.set_status("ok")
-                    return result
-                finally:
-                    span_obj.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
-
-        return sync_span_wrapper
-
-    return decorator
-
-
-@contextmanager
-def start_span(op: str, description: str = "") -> Generator[DummySpan | Any]:
-    """
-    Context manager for creating a Sentry span.
-
-    Parameters
-    ----------
-    op : str
-        The operation name for the span.
-    description : str
-        A description of what the span is doing.
-
-    Yields
-    ------
-    Union[DummySpan, Any]
-        The Sentry span object or a dummy object if Sentry is not initialized.
-    """
-    start_time = time.perf_counter()
-
-    if not sentry_sdk.is_initialized():
-        # Create a dummy context if Sentry is not available
-        dummy = DummySpan()
-        try:
-            yield dummy
-        finally:
-            pass
-    else:
-        with sentry_sdk.start_span(op=op, description=description) as span:
-            try:
-                yield span
-            finally:
-                span.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
-
-
-@contextmanager
-def start_transaction(op: str, name: str, description: str = "") -> Generator[DummyTransaction | Any]:
-    """
-    Context manager for creating a Sentry transaction.
-
-    Parameters
-    ----------
-    op : str
-        The operation name for the transaction.
-    name : str
-        The name for the transaction.
-    description : str
-        A description of what the transaction is doing.
-
-    Yields
-    ------
-    Union[DummyTransaction, Any]
-        The Sentry transaction object or a dummy object if Sentry is not initialized.
-    """
-    start_time = time.perf_counter()
-
-    if not sentry_sdk.is_initialized():
-        # Create a dummy context if Sentry is not available
-        dummy = DummyTransaction()
-        try:
-            yield dummy
-        finally:
-            pass
-    else:
-        with sentry_sdk.start_transaction(op=op, name=name, description=description) as transaction:
-            try:
-                yield transaction
-            finally:
-                transaction.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
diff --git a/tux/utils/sentry_manager.py b/tux/utils/sentry_manager.py
new file mode 100644
index 000000000..7e319ad38
--- /dev/null
+++ b/tux/utils/sentry_manager.py
@@ -0,0 +1,744 @@
+"""
+Sentry Integration Manager.
+
+This module provides the `SentryManager` class, a centralized wrapper for all
+interactions with the Sentry SDK. Its primary responsibilities include:
+
+- **Initialization**: Configuring and initializing the Sentry SDK with the
+  appropriate DSN, release version, and environment settings.
+- **Graceful Shutdown**: Handling OS signals (SIGTERM, SIGINT) to ensure that
+  all pending Sentry events are flushed before the application exits.
+- **Context Management**: Providing methods to enrich Sentry events with
+  contextual data, such as user information, command details, and custom tags.
+- **Event Capturing**: Offering a simplified interface (`capture_exception`,
+  `capture_message`) for sending events to Sentry.
+"""
+
+from __future__ import annotations
+
+import asyncio
+from types import FrameType
+from typing import Any, ClassVar, Literal, cast
+
+import discord
+import sentry_sdk
+from discord import Interaction
+from discord.ext import commands
+from loguru import logger
+from sentry_sdk.integrations.asyncio import AsyncioIntegration
+from sentry_sdk.integrations.loguru import LoguruIntegration
+from sentry_sdk.types import Event, Hint
+
+from tux.utils.config import CONFIG
+from tux.utils.context_utils import get_interaction_context
+from tux.utils.env import get_current_env
+
+# Type alias for Sentry's log level strings.
+LogLevelStr = Literal["fatal", "critical", "error", "warning", "info", "debug"]
+
+# Type alias for a command context or an interaction.
+ContextOrInteraction = commands.Context[commands.Bot] | Interaction
+
+sentry_sdk.set_user(None)
+
+
+class SentryManager:
+    """
+    Handles all interactions with the Sentry SDK for the bot.
+
+    This class acts as a singleton-like manager (though not strictly enforced)
+    for initializing Sentry, capturing events, and managing performance
+    monitoring transactions.
+    """
+
+    # Standard Sentry transaction statuses.
+    # See: https://develop.sentry.dev/sdk/event-payloads/transaction/#transaction-status
+    STATUS: ClassVar[dict[str, str]] = {
+        "OK": "ok",
+        "UNKNOWN": "unknown",
+        "ERROR": "internal_error",
+        "NOT_FOUND": "not_found",
+        "PERMISSION_DENIED": "permission_denied",
+        "INVALID_ARGUMENT": "invalid_argument",
+        "RESOURCE_EXHAUSTED": "resource_exhausted",
+        "UNAUTHENTICATED": "unauthenticated",
+        "CANCELLED": "cancelled",
+    }
+
+    def __init__(self) -> None:
+        """Initialize the SentryManager."""
+        self.active_sentry_transactions: dict[int, Any] = {}
+
+    # --- Setup & Lifecycle ---
+
+    @staticmethod
+    def _before_send(event: Event, hint: Hint) -> Event | None:
+        """
+        Filter and sanitize events before sending to Sentry.
+
+        This hook allows us to:
+        - Remove sensitive information
+        - Filter out noisy errors
+        - Add error fingerprinting for better grouping
+        - Drop events we don't want to track
+        """
+        # Filter out known noisy errors that provide little value
+        if "exc_info" in hint:
+            exc_type, exc_value, _ = hint["exc_info"]
+
+            # Filter out network-related errors that are usually not actionable
+            if exc_type.__name__ in ("ConnectionResetError", "ConnectionAbortedError", "TimeoutError"):
+                return None
+
+            # Add custom fingerprinting for Discord errors
+            if exc_type.__name__.startswith("Discord"):
+                event["fingerprint"] = [exc_type.__name__, str(getattr(exc_value, "code", "unknown"))]
+
+            # Add fingerprinting for database errors
+            elif exc_type.__name__ in ("DatabaseError", "OperationalError", "IntegrityError"):
+                # Group database errors by type and first few words of message
+                error_msg = str(exc_value)[:50] if exc_value else "unknown"
+                event["fingerprint"] = ["database_error", exc_type.__name__, error_msg]
+
+            # Add fingerprinting for command errors
+            elif exc_type.__name__.endswith("CommandError"):
+                command_name = event.get("tags", {}).get("command", "unknown")
+                event["fingerprint"] = ["command_error", exc_type.__name__, command_name]
+
+        # Basic data sanitization - remove potentially sensitive info
+        # Remove sensitive data from request context if present
+        if "request" in event:
+            request = event["request"]
+            if "query_string" in request:
+                request["query_string"] = "[REDACTED]"
+            if "cookies" in request:
+                request["cookies"] = "[REDACTED]"
+
+        return event
+
+    @staticmethod
+    def _get_span_operation_mapping(op: str) -> str:
+        """
+        Map database controller operations to standardized operation types.
+
+        Parameters
+        ----------
+        op : str
+            The original operation name
+
+        Returns
+        -------
+        str
+            The standardized operation type
+        """
+        if not op.startswith("db.controller."):
+            return op
+
+        # Use dictionary lookup instead of if/elif chain
+        operation_mapping = {
+            "get_": "db.read",
+            "find_": "db.read",
+            "create_": "db.create",
+            "update_": "db.update",
+            "increment_": "db.update",
+            "delete_": "db.delete",
+            "count_": "db.count",
+        }
+
+        return next((mapped_op for prefix, mapped_op in operation_mapping.items() if prefix in op), "db.other")
+
+    @staticmethod
+    def _get_transaction_operation_mapping(transaction_name: str) -> str:
+        """
+        Map database controller transaction names to standardized operation types.
+
+        Parameters
+        ----------
+        transaction_name : str
+            The original transaction name
+
+        Returns
+        -------
+        str
+            The standardized transaction operation type
+        """
+        if not transaction_name.startswith("db.controller."):
+            return transaction_name
+
+        # Use dictionary lookup instead of if/elif chain
+        operation_mapping = {
+            "get_": "db.controller.read_operation",
+            "find_": "db.controller.read_operation",
+            "create_": "db.controller.create_operation",
+            "update_": "db.controller.update_operation",
+            "increment_": "db.controller.update_operation",
+            "delete_": "db.controller.delete_operation",
+            "count_": "db.controller.count_operation",
+        }
+
+        return next(
+            (mapped_op for prefix, mapped_op in operation_mapping.items() if prefix in transaction_name),
+            "db.controller.other_operation",
+        )
+
+    @staticmethod
+    def _filter_and_group_spans(spans: list[dict[str, Any]]) -> list[dict[str, Any]]:
+        """
+        Filter and group spans to reduce noise and improve trace readability.
+
+        Parameters
+        ----------
+        spans : list[dict[str, Any]]
+            List of spans to filter and group
+
+        Returns
+        -------
+        list[dict[str, Any]]
+            Filtered and grouped spans
+        """
+        filtered_spans: list[dict[str, Any]] = []
+
+        for span in spans:
+            op = span.get("op", "")
+            description = span.get("description", "")
+
+            # Filter out internal Prisma HTTP requests to the query engine
+            if op == "http.client" and "localhost" in description:
+                continue
+
+            # Filter out noisy, low-level asyncio/library functions
+            if "staggered_race" in description:
+                continue
+
+            # Group database controller operations for cleaner reporting
+            if "db.controller." in op:
+                span["op"] = SentryManager._get_span_operation_mapping(op)
+                # Normalize description for grouped DB operations
+                span["description"] = f"DB {str(span['op']).split('.')[-1].capitalize()} Operation"
+
+            filtered_spans.append(span)
+
+        return filtered_spans
+
+    @staticmethod
+    def _before_send_transaction(event: Event, hint: Hint) -> Event | None:
+        """
+        Filter and modify transaction events before sending to Sentry.
+
+        This helps reduce noise and improve transaction grouping.
+        """
+        if event.get("type") != "transaction":
+            return event
+
+        transaction_name = event.get("transaction", "")
+
+        # Filter out noisy or uninteresting transactions entirely
+        noisy_operations = [
+            "safe_get_attr",
+            "connect_or_create",
+            "_build_",
+            "_add_include",
+            "CogLoader.load_cogs_from_folder",  # Startup noise
+            "CogLoader Setup",  # More startup noise
+            "Bot shutdown process",  # Shutdown noise
+        ]
+
+        if any(op in transaction_name for op in noisy_operations):
+            return None
+
+        # Filter spans to reduce noise and group operations
+        if "spans" in event:
+            spans = cast(list[dict[str, Any]], event.get("spans") or [])
+            event["spans"] = SentryManager._filter_and_group_spans(spans)
+
+        # Group all database controller transactions by type for cleaner reporting
+        if "db.controller." in transaction_name:
+            event["transaction"] = SentryManager._get_transaction_operation_mapping(transaction_name)
+
+        return event
+
+    @staticmethod
+    def _traces_sampler(sampling_context: dict[str, Any]) -> float:
+        """
+        Custom trace sampling function for more granular control over which traces to sample.
+
+        Parameters
+        ----------
+        sampling_context : dict[str, Any]
+            Context information about the transaction
+
+        Returns
+        -------
+        float
+            Sampling rate between 0.0 and 1.0
+        """
+        # Get transaction name for decision making
+        transaction_name = sampling_context.get("transaction_context", {}).get("name", "")
+
+        # Full sampling in development for debugging
+        if get_current_env() in ("dev", "development"):
+            return 1.0
+
+        # Production sampling rates using dictionary lookup
+        sampling_rates = {
+            "db.controller": 0.01,  # 1% sampling for DB operations
+            "db.query": 0.005,  # 0.5% sampling for low-level DB queries
+            "command": 0.1,  # 10% sampling for commands
+            "cog.": 0.02,  # 2% sampling for cog ops
+        }
+
+        # Check for matching patterns and return appropriate sampling rate
+        return next(
+            (rate for pattern, rate in sampling_rates.items() if pattern in transaction_name),
+            0.05,  # Default sampling rate for other operations
+        )
+
+    @staticmethod
+    def setup() -> None:
+        """
+        Initializes the Sentry SDK with configuration from the environment.
+
+        If no Sentry DSN is provided in the configuration, setup is skipped.
+        This method configures the release version, environment, tracing, and
+        enables Sentry's logging integration.
+        """
+        if not CONFIG.SENTRY_DSN:
+            logger.warning("No Sentry DSN configured, skipping Sentry setup")
+            return
+
+        logger.info("Setting up Sentry...")
+
+        try:
+            sentry_sdk.init(
+                # https://docs.sentry.io/platforms/python/configuration/options/#dsn
+                dsn=CONFIG.SENTRY_DSN,
+                # https://docs.sentry.io/platforms/python/configuration/options/#release
+                release=CONFIG.BOT_VERSION,
+                # https://docs.sentry.io/platforms/python/configuration/options/#environment
+                environment=get_current_env(),
+                integrations=[
+                    AsyncioIntegration(),
+                    LoguruIntegration(),
+                ],
+                enable_tracing=True,
+                # https://docs.sentry.io/platforms/python/configuration/options/#attach_stacktrace
+                attach_stacktrace=True,
+                # https://docs.sentry.io/platforms/python/configuration/options/#send_default_pii
+                send_default_pii=False,
+                # https://docs.sentry.io/platforms/python/configuration/options/#traces_sample_rate
+                # Adjust sampling based on environment - 100% for dev, lower for production
+                traces_sample_rate=1.0 if get_current_env() in ("dev", "development") else 0.1,
+                # Set profiles_sample_rate to profile transactions.
+                # We recommend adjusting this value in production.
+                profiles_sample_rate=1.0 if get_current_env() in ("dev", "development") else 0.01,
+                # https://docs.sentry.io/platforms/python/configuration/filtering/#using-before-send
+                before_send=SentryManager._before_send,
+                before_send_transaction=SentryManager._before_send_transaction,
+                # Custom trace sampling function for more granular control
+                traces_sampler=SentryManager._traces_sampler,
+                _experiments={
+                    "enable_logs": True,
+                },
+            )
+            sentry_sdk.set_tag("discord_library_version", discord.__version__)
+            logger.info(f"Sentry initialized: {sentry_sdk.is_initialized()}")
+        except Exception as e:
+            logger.error(f"Failed to initialize Sentry: {e}")
+
+    @staticmethod
+    def _set_signal_scope_tags(scope: Any, signum: int) -> None:
+        """Set signal-related tags on a Sentry scope.
+
+        Parameters
+        ----------
+        scope : Any
+            The Sentry scope to modify
+        signum : int
+            The signal number
+        """
+        tags = {
+            "signal.number": signum,
+            "lifecycle.event": "termination_signal",
+        }
+
+        for key, value in tags.items():
+            scope.set_tag(key, value)
+
+    @staticmethod
+    def report_signal(signum: int, _frame: FrameType | None) -> None:
+        """
+        A signal handler that reports termination signals to Sentry.
+
+        This method is designed to be used with Python's `signal` module.
+        It captures signals like SIGTERM and SIGINT, adds context to Sentry,
+        and then raises a `KeyboardInterrupt` to trigger the bot's graceful
+        shutdown sequence.
+
+        Parameters
+        ----------
+        signum : int
+            The signal number received.
+        _frame : FrameType | None
+            The current stack frame at the time of the signal.
+        """
+        if sentry_sdk.is_initialized():
+            with sentry_sdk.push_scope() as scope:
+                SentryManager._set_signal_scope_tags(scope, signum)
+                sentry_sdk.add_breadcrumb(
+                    category="lifecycle",
+                    message=f"Received termination signal {signum}",
+                    level="info",
+                )
+        raise KeyboardInterrupt
+
+    @staticmethod
+    def flush() -> None:
+        """
+        Flushes all pending Sentry events.
+
+        This should be called during the application's shutdown sequence to
+        ensure that all buffered events are sent before the process exits.
+        """
+        if sentry_sdk.is_initialized():
+            sentry_sdk.flush()
+
+    @staticmethod
+    async def flush_async() -> None:
+        """
+        Asynchronously flushes all pending Sentry events.
+
+        This method prevents blocking the event loop during shutdown by
+        running the synchronous flush operation in an executor.
+        """
+        if sentry_sdk.is_initialized():
+            loop: asyncio.AbstractEventLoop = asyncio.get_running_loop()
+            await loop.run_in_executor(None, SentryManager.flush)
+
+    @property
+    def is_initialized(self) -> bool:
+        """
+        A convenience property to check if the Sentry SDK is active.
+
+        Returns
+        -------
+        bool
+            True if Sentry is initialized, False otherwise.
+        """
+        return sentry_sdk.is_initialized()
+
+    # --- Event Capturing & Context ---
+
+    def capture_exception(
+        self,
+        error: Exception,
+        *,
+        context: dict[str, Any] | None = None,
+        level: LogLevelStr = "error",
+        tags: dict[str, str] | None = None,
+    ) -> str | None:
+        """
+        Captures and reports an exception to Sentry.
+
+        This method enriches the exception report with additional context
+        and tags, providing more insight into the error.
+
+        Parameters
+        ----------
+        error : Exception
+            The exception object to capture.
+        context : dict[str, Any] | None, optional
+            A dictionary of context data to attach to the event.
+        level : LogLevelStr, optional
+            The severity level for the event (e.g., 'error', 'warning').
+        tags : dict[str, str] | None, optional
+            Additional key-value tags to associate with the event.
+
+        Returns
+        -------
+        str | None
+            The Sentry event ID if capture was successful, otherwise None.
+        """
+        if not self.is_initialized:
+            return None
+
+        event_id: str | None = None
+        try:
+            with sentry_sdk.push_scope() as scope:
+                if context:
+                    self._set_scope_context(scope, context)
+
+                scope.level = level
+
+                if tags:
+                    for key, value in tags.items():
+                        scope.set_tag(key, value)
+
+                event_id = sentry_sdk.capture_exception(error)
+
+                if event_id:
+                    logger.trace(f"Reported {type(error).__name__} to Sentry ({event_id})")
+                else:
+                    logger.warning(f"Captured {type(error).__name__} but Sentry returned no ID.")
+        except Exception as e:
+            logger.error(f"Failed to report {type(error).__name__} to Sentry: {e}")
+
+        return event_id
+
+    def capture_message(self, message: str, level: LogLevelStr = "info") -> None:
+        """
+        Captures and reports a message to Sentry.
+
+        Parameters
+        ----------
+        message : str
+            The message string to report.
+        level : LogLevelStr, optional
+            The severity level for the message.
+        """
+        if self.is_initialized:
+            with sentry_sdk.push_scope() as scope:
+                scope.set_level(level)
+                sentry_sdk.capture_message(message)
+                logger.trace(f"Captured message in Sentry: {message}")
+
+    def set_tag(self, key: str, value: Any) -> None:
+        """
+        Sets a tag in the current Sentry scope.
+
+        Tags are indexed key-value pairs that can be used for searching
+        and filtering events in Sentry.
+
+        Parameters
+        ----------
+        key : str
+            The name of the tag.
+        value : Any
+            The value of the tag.
+        """
+        if self.is_initialized:
+            sentry_sdk.set_tag(key, value)
+            logger.trace(f"Set Sentry tag: {key}={value}")
+
+    def set_context(self, key: str, value: dict[str, Any]) -> None:
+        """
+        Sets context data in the current Sentry scope.
+
+        Context provides additional, non-indexed data that is displayed
+        on the Sentry event page.
+
+        Parameters
+        ----------
+        key : str
+            The name of the context group (e.g., 'discord', 'user_info').
+        value : dict[str, Any]
+            A dictionary of context data.
+        """
+        if self.is_initialized:
+            sentry_sdk.set_context(key, value)
+            logger.trace(f"Set Sentry context for {key}.")
+
+    # --- Transaction Management ---
+
+    def finish_transaction_on_error(self) -> None:
+        """
+        Finds and finishes an active Sentry transaction with an error status.
+
+        This method should be called from an error handler. It automatically
+        accesses the current span and sets its status to 'internal_error'.
+        """
+        if not self.is_initialized:
+            return
+
+        if span := sentry_sdk.get_current_span():
+            span.set_status(self.STATUS["ERROR"])
+            logger.trace("Set Sentry span status to 'internal_error' for errored command.")
+
+    # --- Internal Helpers ---
+
+    def _set_scope_context(self, scope: Any, context: dict[str, Any]) -> None:
+        """
+        Sets user, context, and tags on a Sentry scope from a context dictionary.
+
+        Parameters
+        ----------
+        scope : Any
+            The Sentry scope object to modify.
+        context : dict[str, Any]
+            A dictionary of context data.
+        """
+        scope.set_user({"id": context.get("user_id"), "username": context.get("user_name")})
+        scope.set_context("discord", context)
+
+        # Set tags using a dictionary to avoid repetitive set_tag calls
+        tags = {
+            "command_name": context.get("command_name", "Unknown"),
+            "command_type": context.get("command_type", "Unknown"),
+            "guild_id": str(context.get("guild_id")) if context.get("guild_id") else "DM",
+        }
+
+        for key, value in tags.items():
+            scope.set_tag(key, value)
+
+    def set_user_context(self, user: discord.User | discord.Member) -> None:
+        """
+        Sets the user context for the current Sentry scope.
+
+        This provides valuable information for debugging user-specific issues.
+
+        Parameters
+        ----------
+        user : discord.User | discord.Member
+            The Discord user or member to set as context.
+        """
+        if not self.is_initialized:
+            return
+
+        user_data: dict[str, Any] = {
+            "id": str(user.id),
+            "username": user.name,
+            "display_name": user.display_name,
+            "bot": user.bot,
+            "created_at": user.created_at.isoformat(),
+        }
+
+        # Add member-specific data if available
+        if isinstance(user, discord.Member):
+            member_data = {
+                "guild_id": str(user.guild.id),
+                "guild_name": user.guild.name,
+                "nick": user.nick,
+                "joined_at": user.joined_at.isoformat() if user.joined_at else None,
+                "roles": [role.name for role in user.roles[1:]],  # Exclude @everyone
+                "premium_since": user.premium_since.isoformat() if user.premium_since else None,
+            }
+            user_data |= member_data
+
+        sentry_sdk.set_user(user_data)
+        logger.trace(f"Set Sentry user context for {user.name}")
+
+    def set_command_context(self, ctx: ContextOrInteraction) -> None:
+        """
+        Sets comprehensive command context for the current Sentry scope using existing context utilities.
+
+        This enriches error reports with command-specific information.
+
+        Parameters
+        ----------
+        ctx : ContextOrInteraction
+            The command context or interaction.
+        """
+        if not self.is_initialized:
+            return
+
+        # Use existing context utilities to get standardized context data
+        context_data = get_interaction_context(ctx)
+
+        # Set user context
+        user = ctx.user if isinstance(ctx, Interaction) else ctx.author
+        self.set_user_context(user)
+
+        # Set guild context if available
+        if ctx.guild:
+            guild_data = {
+                "id": str(ctx.guild.id),
+                "name": ctx.guild.name,
+                "member_count": ctx.guild.member_count,
+                "created_at": ctx.guild.created_at.isoformat(),
+                "owner_id": str(ctx.guild.owner_id) if ctx.guild.owner_id else None,
+                "verification_level": ctx.guild.verification_level.name,
+                "premium_tier": ctx.guild.premium_tier,
+                "preferred_locale": str(ctx.guild.preferred_locale),
+            }
+            self.set_context("guild", guild_data)
+
+        # Set command context using standardized data
+        self.set_context("command", context_data)
+
+    # --- Tracing and Span Management ---
+
+    def get_current_span(self) -> Any | None:
+        """
+        Get the current active span from Sentry.
+
+        Returns
+        -------
+        Any | None
+            The current span if Sentry is initialized and a span is active, None otherwise.
+        """
+        return sentry_sdk.get_current_span() if self.is_initialized else None
+
+    def start_transaction(self, op: str, name: str, description: str = "") -> Any:
+        """
+        Start a new Sentry transaction.
+
+        Parameters
+        ----------
+        op : str
+            The operation name for the transaction.
+        name : str
+            The name of the transaction.
+        description : str, optional
+            A description of the transaction.
+
+        Returns
+        -------
+        Any
+            The started transaction object.
+        """
+        return (
+            sentry_sdk.start_transaction(
+                op=op,
+                name=name,
+                description=description,
+            )
+            if self.is_initialized
+            else None
+        )
+
+    def start_span(self, op: str, description: str = "") -> Any:
+        """
+        Start a new Sentry span.
+
+        Parameters
+        ----------
+        op : str
+            The operation name for the span.
+        description : str, optional
+            A description of the span.
+
+        Returns
+        -------
+        Any
+            The started span object.
+        """
+        return sentry_sdk.start_span(op=op, description=description) if self.is_initialized else None
+
+    def add_breadcrumb(
+        self,
+        message: str,
+        category: str = "default",
+        level: LogLevelStr = "info",
+        data: dict[str, Any] | None = None,
+    ) -> None:
+        """
+        Add a breadcrumb to the current Sentry scope.
+
+        Parameters
+        ----------
+        message : str
+            The breadcrumb message.
+        category : str, optional
+            The breadcrumb category.
+        level : LogLevelStr, optional
+            The breadcrumb level.
+        data : dict[str, Any] | None, optional
+            Additional data for the breadcrumb.
+        """
+        if not self.is_initialized:
+            return
+        sentry_sdk.add_breadcrumb(
+            message=message,
+            category=category,
+            level=level,
+            data=data,
+        )
diff --git a/tux/utils/task_manager.py b/tux/utils/task_manager.py
new file mode 100644
index 000000000..552061e13
--- /dev/null
+++ b/tux/utils/task_manager.py
@@ -0,0 +1,761 @@
+"""
+Asynchronous Task Management Utility.
+
+This module provides the `TaskManager` class, which encapsulates the logic for
+monitoring, categorizing, and managing the lifecycle of asyncio tasks within the
+bot. By abstracting this functionality, it keeps the main `Tux` class cleaner
+and more focused on its core responsibilities.
+
+The manager is responsible for:
+- Periodically monitoring all running asyncio tasks.
+- Categorizing tasks based on their naming conventions (e.g., discord.py
+  internal tasks, scheduled tasks, command tasks).
+- Gracefully stopping and cancelling tasks during the bot's shutdown sequence.
+- Health monitoring and automatic recovery of critical tasks.
+- Collecting performance metrics and statistics.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import contextlib
+import functools
+import time
+from collections import defaultdict, deque
+from collections.abc import Callable, Coroutine
+from dataclasses import dataclass, field
+from enum import Enum, auto
+from typing import Any, ClassVar, NamedTuple, Protocol, cast, runtime_checkable
+
+from discord.ext import tasks
+from loguru import logger
+
+from tux.utils.protocols import BotProtocol
+from tux.utils.tracing import start_span, transaction
+
+
+def instrumented_task(coro: Callable[..., Coroutine[Any, Any, Any]]) -> Callable[..., Coroutine[Any, Any, Any]]:
+    """
+    Decorator to instrument a task coroutine for monitoring/metrics.
+    Apply this decorator to critical task coroutines at definition time.
+    """
+
+    @functools.wraps(coro)
+    async def wrapper(*args: Any, **kwargs: Any) -> Any:
+        # Insert instrumentation logic here (e.g., Sentry, metrics, logging)
+        # Start timing, add tracing, etc.
+        return await coro(*args, **kwargs)
+
+    return wrapper
+
+
+class TaskCategory(Enum):
+    """Categories for background tasks."""
+
+    SCHEDULED = auto()
+    GATEWAY = auto()
+    SYSTEM = auto()
+    COMMAND = auto()
+    UNKNOWN = auto()
+
+
+class TaskPriority(Enum):
+    """Task priority levels for shutdown ordering."""
+
+    CRITICAL = auto()  # Essential tasks (database, core services)
+    HIGH = auto()  # Important tasks (moderation, reminders)
+    NORMAL = auto()  # Regular tasks (levels, starboard)
+    LOW = auto()  # Optional tasks (status, activities)
+
+
+@dataclass
+class TaskMetrics:
+    """Metrics tracking for individual tasks."""
+
+    name: str
+    category: TaskCategory
+    priority: TaskPriority = TaskPriority.NORMAL
+    start_time: float = field(default_factory=time.time)
+    restart_count: int = 0
+    last_restart: float | None = None
+    total_runtime: float = 0.0
+    avg_runtime: float = 0.0
+    max_runtime: float = 0.0
+    error_count: int = 0
+    last_error: str | None = None
+    last_error_time: float | None = None
+
+
+class TaskHealth(NamedTuple):
+    """Health status of a task."""
+
+    is_healthy: bool
+    uptime: float
+    error_rate: float
+    restart_count: int
+    last_seen: float
+
+
+@dataclass
+class CriticalTaskConfig:
+    """Configuration for critical tasks that should be monitored and restarted."""
+
+    name: str
+    cog_name: str
+    task_attr: str
+    priority: TaskPriority = TaskPriority.HIGH
+    max_restarts: int = 5
+    restart_delay: float = 30.0
+    health_check_interval: float = 300.0  # 5 minutes
+
+
+@runtime_checkable
+class CriticalTasksProvider(Protocol):
+    """Protocol for cogs that provide critical tasks."""
+
+    def get_critical_tasks(self) -> list[CriticalTaskConfig]: ...
+
+
+class TaskManager:
+    """
+    Enhanced task manager with health monitoring, metrics, and recovery capabilities.
+
+    Manages the lifecycle of asyncio tasks for the bot with advanced features:
+    - Task registration and health monitoring
+    - Automatic recovery of failed critical tasks
+    - Performance metrics and statistics collection
+    """
+
+    # This mapping is used to categorize tasks based on the prefix of their names.
+    # It allows for easy identification of tasks from specific libraries or systems.
+    TASK_PREFIX_MAP: ClassVar[dict[tuple[str, ...], TaskCategory]] = {
+        ("discord-ext-tasks:",): TaskCategory.SCHEDULED,
+        ("discord.py:", "discord-voice-", "discord-gateway-"): TaskCategory.GATEWAY,
+        ("patch_asyncio",): TaskCategory.SYSTEM,
+    }
+
+    def __init__(self, bot: BotProtocol) -> None:
+        """
+        Initialize the TaskManager with enhanced monitoring capabilities.
+
+        Parameters
+        ----------
+        bot : BotProtocol
+            The bot instance that conforms to the protocol.
+        """
+        self.bot = bot
+
+        # Task registration and monitoring
+        self.critical_tasks: dict[str, CriticalTaskConfig] = {}
+        self.task_metrics: dict[str, TaskMetrics] = {}
+        self.task_history: dict[str, deque[float]] = defaultdict(lambda: deque(maxlen=100))
+
+        # Health monitoring
+        self.last_health_check: float = 0.0
+        self.health_check_interval: float = 300.0  # 5 minutes
+
+        # Note: Critical tasks are now registered after cogs are loaded
+        # to ensure cogs exist before registering their tasks
+
+    def setup_task_instrumentation(self) -> None:
+        """
+        Initializes instrumentation for all registered critical tasks.
+
+        To ensure compatibility with discord.py and avoid relying on internal
+        implementation details, critical task coroutines should be wrapped with
+        the @instrumented_task decorator at definition time. This ensures that
+        instrumentation is applied in a supported and robust manner.
+
+        Example usage:
+            @instrumented_task
+            async def my_critical_task(...):
+                ...
+
+        This method can still be used for any additional setup or validation.
+        """
+        logger.info("Validating Sentry instrumentation for critical tasks...")
+
+        for task_name, config in self.critical_tasks.items():
+            if not (cog := self.bot.cogs.get(config.cog_name)):
+                logger.warning(f"Cog {config.cog_name} not found for task {task_name}. Skipping instrumentation.")
+                continue
+
+            if not (task_loop := getattr(cog, config.task_attr, None)):
+                logger.warning(
+                    f"Task loop {config.task_attr} not found in cog {config.cog_name}. Skipping instrumentation.",
+                )
+                continue
+
+            if isinstance(task_loop, tasks.Loop):
+                try:
+                    # We are confident .coro exists and is a callable coroutine on a tasks.Loop instance.
+                    # The type checker struggles with this dynamic attribute from the discord.py library.
+                    original_coro = cast(Callable[..., Coroutine[Any, Any, None]], task_loop.coro)  # type: ignore[attr-defined]
+                    decorated_loop = transaction(op="task.run", name=f"task.{task_name}")(original_coro)
+                    task_loop.coro = decorated_loop  # type: ignore[attr-defined]
+                    logger.debug(f"Instrumented task: {task_name}")
+                except AttributeError:
+                    logger.warning(f"Could not find a 'coro' on task {task_name}. Skipping instrumentation.")
+            else:
+                logger.warning(
+                    f"Attribute {config.task_attr} in {config.cog_name} is not a Loop. Skipping instrumentation.",
+                )
+
+    # --- Public Methods ---
+
+    def start(self) -> None:
+        """Starts the background task monitoring loop if it's not already running."""
+        if not self._monitor_tasks_loop.is_running():
+            self._monitor_tasks_loop.start()
+            logger.debug("Task monitoring loop started.")
+        logger.debug("Enhanced task monitoring started.")
+
+    def stop(self) -> None:
+        """Stops the background task monitoring loop."""
+        if self._monitor_tasks_loop.is_running():
+            self._monitor_tasks_loop.stop()
+        logger.debug("Enhanced task monitoring stopped.")
+
+    def register_critical_task(self, config: CriticalTaskConfig) -> None:
+        """
+        Register a critical task for health monitoring and recovery.
+
+        Parameters
+        ----------
+        config : CriticalTaskConfig
+            Configuration for the critical task to register.
+        """
+        self.critical_tasks[config.name] = config
+        self.task_metrics[config.name] = TaskMetrics(
+            name=config.name,
+            category=TaskCategory.SCHEDULED,
+            priority=config.priority,
+        )
+        logger.debug(f"Registered critical task: {config.name}")
+
+    def discover_and_register_cog_tasks(self) -> None:
+        """
+        Discover and register critical tasks from all loaded cogs.
+
+        This method iterates through all loaded cogs and looks for a
+        `get_critical_tasks` method. If found, it calls the method to
+        get a list of CriticalTaskConfig objects and registers them.
+        """
+        for cog_name, cog in self.bot.cogs.items():
+            if isinstance(cog, CriticalTasksProvider):
+                try:
+                    task_configs = cog.get_critical_tasks()
+                    for config in task_configs:
+                        self.register_critical_task(config)
+                        logger.debug(f"Discovered task {config.name} from cog {cog_name}")
+                except Exception as e:
+                    logger.warning(f"Error discovering tasks from cog {cog_name}: {e}")
+                    continue
+
+    def unregister_critical_task(self, task_name: str) -> None:
+        """
+        Unregister a critical task when its cog is unloaded.
+
+        Parameters
+        ----------
+        task_name : str
+            The name of the task to unregister.
+        """
+        if task_name in self.critical_tasks:
+            del self.critical_tasks[task_name]
+            logger.debug(f"Unregistered critical task: {task_name}")
+
+        if task_name in self.task_metrics:
+            del self.task_metrics[task_name]
+            logger.debug(f"Removed metrics for task: {task_name}")
+
+    def cleanup_cog_tasks(self, cog_name: str) -> None:
+        """
+        Clean up all critical tasks associated with a specific cog.
+
+        Parameters
+        ----------
+        cog_name : str
+            The name of the cog that was unloaded.
+        """
+        tasks_to_remove = [
+            task_name for task_name, config in self.critical_tasks.items() if config.cog_name == cog_name
+        ]
+
+        for task_name in tasks_to_remove:
+            self.unregister_critical_task(task_name)
+
+        if tasks_to_remove:
+            logger.info(f"Cleaned up {len(tasks_to_remove)} critical tasks for unloaded cog: {cog_name}")
+
+    def get_task_health(self, task_name: str) -> TaskHealth | None:
+        """
+        Get health status for a specific task.
+
+        Parameters
+        ----------
+        task_name : str
+            The name of the task to check.
+
+        Returns
+        -------
+        TaskHealth | None
+            Health status or None if task not found.
+        """
+        if (metrics := self.task_metrics.get(task_name)) is None:
+            return None
+
+        current_time = time.time()
+        uptime = current_time - metrics.start_time
+
+        # Calculate error rate (errors per hour)
+        error_rate = (metrics.error_count / max(uptime / 3600, 0.1)) if uptime > 0 else 0.0
+
+        # Task is healthy if it has low error rate and hasn't been restarting frequently
+        is_healthy = (
+            error_rate < 10.0  # Less than 10 errors per hour
+            and metrics.restart_count < 3  # Less than 3 restarts
+            and (not metrics.last_restart or current_time - metrics.last_restart > 300)  # No restart in last 5 minutes
+        )
+
+        return TaskHealth(
+            is_healthy=is_healthy,
+            uptime=uptime,
+            error_rate=error_rate,
+            restart_count=metrics.restart_count,
+            last_seen=current_time,
+        )
+
+    def get_task_statistics(self) -> dict[str, Any]:
+        """
+        Get comprehensive task statistics.
+
+        Returns
+        -------
+        dict[str, Any]
+            Statistics about all monitored tasks.
+        """
+        # Initialize counters
+        healthy_tasks = 0
+        unhealthy_tasks = 0
+        total_restarts = 0
+        total_errors = 0
+        categories: defaultdict[str, int] = defaultdict(int)
+        priorities: defaultdict[str, int] = defaultdict(int)
+
+        for task_name, metrics in self.task_metrics.items():
+            if health := self.get_task_health(task_name):
+                if health.is_healthy:
+                    healthy_tasks += 1
+                else:
+                    unhealthy_tasks += 1
+
+            categories[metrics.category.name] += 1
+            priorities[metrics.priority.name] += 1
+            total_restarts += metrics.restart_count
+            total_errors += metrics.error_count
+
+        return {
+            "total_tasks": len(self.task_metrics),
+            "critical_tasks": len(self.critical_tasks),
+            "healthy_tasks": healthy_tasks,
+            "unhealthy_tasks": unhealthy_tasks,
+            "categories": dict(categories),
+            "priorities": dict(priorities),
+            "total_restarts": total_restarts,
+            "total_errors": total_errors,
+        }
+
+    async def restart_critical_task(self, task_name: str) -> bool:  # noqa: PLR0911
+        """
+        Attempt to restart a critical task.
+
+        Parameters
+        ----------
+        task_name : str
+            The name of the task to restart.
+
+        Returns
+        -------
+        bool
+            True if restart was successful, False otherwise.
+        """
+        # Validate task is critical and get config/metrics
+        if task_name not in self.critical_tasks:
+            logger.warning(f"Cannot restart non-critical task: {task_name}")
+            return False
+
+        config = self.critical_tasks[task_name]
+        metrics = self.task_metrics[task_name]
+        current_time = time.time()
+
+        # Check restart constraints
+        if metrics.restart_count >= config.max_restarts:
+            logger.error(f"Task {task_name} has exceeded max restarts ({config.max_restarts})")
+            return False
+
+        if metrics.last_restart and current_time - metrics.last_restart < config.restart_delay:
+            logger.warning(f"Task {task_name} is in restart cooldown")
+            return False
+
+        # Find and validate the cog and task
+        cog = self.bot.cogs.get(config.cog_name)
+        if not cog:
+            logger.error(f"Cog {config.cog_name} not found for task {task_name}")
+            return False
+
+        task_loop = getattr(cog, config.task_attr, None)
+        if not isinstance(task_loop, tasks.Loop):
+            logger.error(f"Task {config.task_attr} not found in cog {config.cog_name}")
+            return False
+
+        # Attempt restart
+        try:
+            if task_loop.is_running():
+                task_loop.restart()
+            else:
+                task_loop.start()
+        except Exception as e:
+            logger.error(f"Failed to restart task {task_name}: {e}")
+            self.bot.sentry_manager.capture_exception(e)
+            return False
+        else:
+            # Update metrics on successful restart
+            metrics.restart_count += 1
+            metrics.last_restart = current_time
+            metrics.start_time = current_time
+
+            logger.info(f"Successfully restarted critical task: {task_name}")
+            return True
+
+    async def cancel_all_tasks(self) -> None:
+        """
+        Gracefully cancels all managed asyncio tasks with priority ordering.
+
+        This is the main entrypoint for the shutdown process. It stops all
+        `discord.ext.tasks` loops and then proceeds to cancel all other
+        categorized tasks in priority order.
+        """
+        with start_span("bot.cleanup_tasks", "Cleaning up running tasks"):
+            try:
+                await self._stop_task_loops()
+
+                all_tasks = [t for t in asyncio.all_tasks() if t is not asyncio.current_task()]
+                tasks_by_type = self._categorize_tasks(all_tasks)
+
+                # Cancel tasks in priority order (low priority first)
+                await self._cancel_tasks_by_priority(tasks_by_type)
+
+            except Exception as e:
+                logger.error(f"Error during task cleanup: {e}")
+                self.bot.sentry_manager.capture_exception(e)
+
+    # --- Monitoring Loop ---
+
+    @tasks.loop(seconds=60)
+    async def _monitor_tasks_loop(self) -> None:
+        """
+        Enhanced task monitoring with health checks and metrics collection.
+
+        This loop runs every 60 seconds to gather all tasks, categorize them,
+        handle finished tasks, perform health checks, and collect metrics.
+
+        Raises
+        ------
+        RuntimeError
+            If a critical, unhandled exception occurs during task monitoring.
+        """
+        with start_span("bot.monitor_tasks", "Monitoring async tasks"):
+            try:
+                current_time = time.time()
+                all_tasks = [t for t in asyncio.all_tasks() if t is not asyncio.current_task()]
+                tasks_by_type = self._categorize_tasks(all_tasks)
+
+            except Exception as e:
+                logger.error(f"Error during task categorization: {e}")
+                self.bot.sentry_manager.capture_exception(e)
+                return
+
+            try:
+                await self._process_finished_tasks(tasks_by_type)
+            except Exception as e:
+                logger.error(f"Error processing finished tasks: {e}")
+                self.bot.sentry_manager.capture_exception(e)
+
+            try:
+                self._update_task_metrics(tasks_by_type, current_time)
+            except Exception as e:
+                logger.error(f"Error updating task metrics: {e}")
+                self.bot.sentry_manager.capture_exception(e)
+
+            try:
+                if current_time - self.last_health_check > self.health_check_interval:
+                    await self._perform_health_checks()
+                    self.last_health_check = current_time
+            except Exception as e:
+                logger.error(f"Error performing health checks: {e}")
+                self.bot.sentry_manager.capture_exception(e)
+
+    # --- Task Categorization & Processing ---
+
+    def _categorize_tasks(self, tasks: list[asyncio.Task[Any]]) -> dict[TaskCategory, list[asyncio.Task[Any]]]:
+        """
+        Categorizes a list of tasks based on their names.
+
+        Parameters
+        ----------
+        tasks : list[asyncio.Task[Any]]
+            The list of asyncio tasks to categorize.
+
+        Returns
+        -------
+        dict[TaskCategory, list[asyncio.Task[Any]]]
+            A dictionary mapping each task category to a list of tasks.
+        """
+        tasks_by_type: dict[TaskCategory, list[asyncio.Task[Any]]] = {category: [] for category in TaskCategory}
+
+        for task in tasks:
+            if task.done():
+                continue
+
+            name = self._get_task_name(task)
+            category = self._get_task_category(name)
+            tasks_by_type.setdefault(category, []).append(task)
+
+        if unknown_tasks := tasks_by_type.get(TaskCategory.UNKNOWN):
+            task_names = [self._get_task_name(t) for t in unknown_tasks]
+            logger.warning(f"Found {len(unknown_tasks)} uncategorized tasks: {', '.join(task_names)}")
+
+        return tasks_by_type
+
+    def _get_task_category(self, name: str) -> TaskCategory:
+        """
+        Determines the category of a task from its name.
+
+        It first checks against the `TASK_PREFIX_MAP` for known system/library
+        tasks, then checks for command-related tasks, and finally defaults
+        to a general system task.
+
+        Parameters
+        ----------
+        name : str
+            The name of the asyncio task.
+
+        Returns
+        -------
+        TaskCategory
+            The determined category for the task.
+        """
+        if name in self.critical_tasks:
+            return TaskCategory.SCHEDULED
+
+        # Default asyncio tasks (e.g., Task-1) are considered SYSTEM tasks.
+        if name.startswith("Task-"):
+            return TaskCategory.SYSTEM
+
+        return next(
+            (
+                category
+                for prefixes, category in self.TASK_PREFIX_MAP.items()
+                if any(name.startswith(p) for p in prefixes)
+            ),
+            (TaskCategory.COMMAND if "command_" in name.lower() else TaskCategory.UNKNOWN),
+        )
+
+    async def _process_finished_tasks(self, tasks_by_type: dict[TaskCategory, list[asyncio.Task[Any]]]) -> None:
+        """
+        Awaits any tasks that have already completed to handle their results.
+
+        This is important for preventing "awaitable was never awaited" warnings
+        and ensuring that exceptions from completed tasks are raised and logged.
+
+        Parameters
+        ----------
+        tasks_by_type : dict[TaskCategory, list[asyncio.Task[Any]]]
+            A dictionary of tasks, categorized by type.
+        """
+        for task_list in tasks_by_type.values():
+            for task in task_list:
+                if task.done():
+                    with contextlib.suppress(asyncio.CancelledError):
+                        try:
+                            await task
+                        except Exception as e:
+                            # Log task exceptions and update metrics
+                            logger.error(f"Task {(task_name := self._get_task_name(task))} failed with exception: {e}")
+                            self._record_task_error(task_name, str(e))
+
+    def _update_task_metrics(
+        self,
+        tasks_by_type: dict[TaskCategory, list[asyncio.Task[Any]]],
+        current_time: float,
+    ) -> None:
+        """
+        Update metrics for all running tasks.
+
+        Parameters
+        ----------
+        tasks_by_type : dict[TaskCategory, list[asyncio.Task[Any]]]
+            Categorized tasks.
+        current_time : float
+            Current timestamp.
+        """
+        # Update runtime metrics for critical tasks
+        for task_name, config in self.critical_tasks.items():
+            if cog := self.bot.cogs.get(config.cog_name):
+                task_loop = getattr(cog, config.task_attr, None)
+                if isinstance(task_loop, tasks.Loop) and task_loop.is_running():
+                    metrics = self.task_metrics[task_name]
+                    metrics.total_runtime = current_time - metrics.start_time
+                    self.task_history[task_name].append(current_time)
+
+    async def _perform_health_checks(self) -> None:
+        """Perform health checks on all critical tasks."""
+        unhealthy_tasks: list[str] = []
+
+        for task_name, config in self.critical_tasks.items():
+            cog = self.bot.cogs.get(config.cog_name)
+            if not cog:
+                logger.warning(f"Cog {config.cog_name} not found for critical task {task_name}")
+                continue
+
+            task_loop = getattr(cog, config.task_attr, None)
+            if not isinstance(task_loop, tasks.Loop):
+                logger.warning(f"Task {config.task_attr} not found in cog {config.cog_name}")
+                continue
+
+            # Check if task is running
+            if not task_loop.is_running():
+                logger.warning(f"Critical task {task_name} is not running")
+                unhealthy_tasks.append(task_name)
+                continue
+
+            # Check task health
+            health = self.get_task_health(task_name)
+            if health and not health.is_healthy:
+                logger.warning(f"Critical task {task_name} is unhealthy: {health}")
+                unhealthy_tasks.append(task_name)
+
+        # Attempt to restart unhealthy critical tasks
+        for task_name in unhealthy_tasks:
+            if await self.restart_critical_task(task_name):
+                logger.info(f"Successfully recovered unhealthy task: {task_name}")
+
+    def _record_task_error(self, task_name: str, error_msg: str) -> None:
+        """
+        Record an error for a task.
+
+        Parameters
+        ----------
+        task_name : str
+            The name of the task.
+        error_msg : str
+            The error message.
+        """
+        if task_name in self.task_metrics:
+            metrics = self.task_metrics[task_name]
+            metrics.error_count += 1
+            metrics.last_error = error_msg
+            metrics.last_error_time = time.time()
+
+    # --- Shutdown & Cleanup ---
+
+    async def _stop_task_loops(self) -> None:
+        """
+        Stops all registered `discord.ext.tasks.Loop` instances in all cogs.
+
+        This is a critical first step in the cleanup process to prevent new
+        tasks from being created while shutdown is in progress.
+        """
+        with start_span("bot.stop_task_loops", "Stopping task loops"):
+            for cog_name, cog in self.bot.cogs.items():
+                if not cog:
+                    continue
+
+                for name, value in cog.__dict__.items():
+                    if isinstance(value, tasks.Loop):
+                        try:
+                            value.stop()
+                            logger.debug(f"Stopped task loop {cog_name}.{name}")
+                        except Exception as e:
+                            logger.error(f"Error stopping task loop {cog_name}.{name}: {e}")
+
+            # Only stop the monitor loop if all cog tasks were processed without critical errors
+            if self._monitor_tasks_loop.is_running():
+                self._monitor_tasks_loop.stop()
+
+    @staticmethod
+    def _get_task_name(task: asyncio.Task[Any]) -> str:
+        """
+        Gets a descriptive name for an asyncio task.
+
+        If a task was not explicitly named, it attempts to derive a name
+        from its coroutine object for better logging.
+
+        Parameters
+        ----------
+        task : asyncio.Task[Any]
+            The asyncio task to get the name from.
+
+        Returns
+        -------
+        str
+            A descriptive name for the task.
+        """
+        name = task.get_name() or "unnamed"
+        if name in ("None", "unnamed"):
+            coro = task.get_coro()
+            name = getattr(coro, "__qualname__", str(coro))
+        return name
+
+    async def _cancel_tasks_by_priority(self, tasks_by_type: dict[TaskCategory, list[asyncio.Task[Any]]]) -> None:
+        """
+        Cancel tasks in priority order (low priority first).
+
+        Parameters
+        ----------
+        tasks_by_type : dict[TaskCategory, list[asyncio.Task[Any]]]
+            The dictionary of tasks to be cancelled.
+        """
+        # Define shutdown priority order (low priority first)
+        shutdown_order = [
+            TaskCategory.UNKNOWN,
+            TaskCategory.COMMAND,
+            TaskCategory.SYSTEM,
+            TaskCategory.SCHEDULED,
+            TaskCategory.GATEWAY,
+        ]
+
+        with start_span("bot.cancel_tasks", "Cancelling tasks by priority") as span:
+            for category in shutdown_order:
+                task_list = tasks_by_type.get(category, [])
+                if not task_list:
+                    continue
+
+                task_names = [self._get_task_name(t) for t in task_list]
+                names = ", ".join(task_names)
+
+                logger.debug(f"Cancelling {len(task_list)} {category.name}: {names}")
+                span.set_data(f"tasks.{category.name.lower()}", task_names)
+
+                for task in task_list:
+                    task.cancel()
+
+                results = await asyncio.gather(*task_list, return_exceptions=True)
+
+                for result in results:
+                    if isinstance(result, Exception) and not isinstance(result, asyncio.CancelledError):
+                        logger.error(f"Exception during task cancellation for {category.name}: {result!r}")
+
+                logger.debug(f"Cancelled {category.name}")
+
+    async def _cancel_tasks(self, tasks_by_type: dict[TaskCategory, list[asyncio.Task[Any]]]) -> None:
+        """
+        Legacy method - redirects to priority-based cancellation.
+
+        Parameters
+        ----------
+        tasks_by_type : dict[TaskCategory, list[asyncio.Task[Any]]]
+            The dictionary of tasks to be cancelled.
+        """
+        await self._cancel_tasks_by_priority(tasks_by_type)
diff --git a/tux/utils/tracing.py b/tux/utils/tracing.py
new file mode 100644
index 000000000..b34a0f5de
--- /dev/null
+++ b/tux/utils/tracing.py
@@ -0,0 +1,592 @@
+"""
+Sentry Instrumentation Utilities for Tracing and Performance Monitoring.
+
+This module provides a set of decorators and context managers to simplify the
+instrumentation of code with Sentry transactions and spans. It standardizes the
+creation of performance monitoring traces and ensures that they gracefully handle
+cases where the Sentry SDK is not initialized by providing dummy objects.
+
+The main components are:
+- Decorators (`@transaction`, `@span`): For easily wrapping entire functions or
+  methods in a Sentry transaction or span.
+- Context Managers (`start_transaction`, `start_span`): For instrumenting
+  specific blocks of code within a function.
+- Helper Functions: For adding contextual data to the currently active span.
+"""
+
+import asyncio
+import functools
+import time
+import traceback
+from collections.abc import Callable, Coroutine, Generator
+from contextlib import contextmanager
+from typing import Any, ParamSpec, TypeVar, cast
+
+import sentry_sdk
+from discord.ext import commands
+from loguru import logger
+
+# Type variables for better type hints with generic functions
+P = ParamSpec("P")
+T = TypeVar("T")
+R = TypeVar("R")
+
+
+# --- Dummy Objects for Graceful Failure ---
+
+
+class DummySpan:
+    """
+    A no-op (dummy) span object for when the Sentry SDK is not initialized.
+
+    This class mimics the interface of a Sentry span but performs no actions,
+    allowing instrumentation code (`with start_span(...)`) to run without errors
+    even if Sentry is disabled.
+    """
+
+    def __init__(self) -> None:
+        """Initialize the dummy span."""
+        self.start_time = time.perf_counter()
+
+    def set_tag(self, *args: Any, **kwargs: Any) -> "DummySpan":
+        """No-op tag setter."""
+        return self
+
+    def set_data(self, *args: Any, **kwargs: Any) -> "DummySpan":
+        """No-op data setter."""
+        return self
+
+    def set_status(self, *args: Any, **kwargs: Any) -> "DummySpan":
+        """No-op status setter."""
+        return self
+
+    def set_name(self, name: str) -> "DummySpan":
+        """No-op name setter."""
+        return self
+
+
+class DummyTransaction(DummySpan):
+    """
+    A no-op (dummy) transaction object for when Sentry is not initialized.
+
+    This inherits from `DummySpan` and provides a safe fallback for the
+    `start_transaction` context manager.
+    """
+
+
+# --- Common Helpers ---
+
+
+def safe_set_name(obj: Any, name: str) -> None:
+    """
+    Safely set the name on a span or transaction object.
+
+    This helper is used because the `set_name` method may not always be
+    present on all span-like objects from Sentry, so this avoids
+    potential `AttributeError` exceptions.
+
+    Parameters
+    ----------
+    obj : Any
+        The span or transaction object.
+    name : str
+        The name to set.
+    """
+    if hasattr(obj, "set_name"):
+        # Use getattr to avoid static type checking issues
+        set_name_func = obj.set_name
+        set_name_func(name)
+
+
+def _handle_exception_in_sentry_context(context_obj: Any, exception: Exception) -> None:
+    """
+    Handle exceptions in a Sentry context (span or transaction) with consistent patterns.
+
+    Parameters
+    ----------
+    context_obj : Any
+        The Sentry span or transaction object.
+    exception : Exception
+        The exception that occurred.
+    """
+    context_obj.set_status("internal_error")
+    context_obj.set_data("error", str(exception))
+    context_obj.set_data("traceback", traceback.format_exc())
+
+
+def _finalize_sentry_context(context_obj: Any, start_time: float) -> None:
+    """
+    Finalize a Sentry context with timing information.
+
+    Parameters
+    ----------
+    context_obj : Any
+        The Sentry span or transaction object.
+    start_time : float
+        The start time for duration calculation.
+    """
+    context_obj.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
+
+
+def create_instrumentation_wrapper[**P, R](
+    func: Callable[P, R],
+    context_factory: Callable[[], Any],
+    is_transaction: bool = False,
+) -> Callable[P, R]:
+    """
+    Creates an instrumentation wrapper for both sync and async functions.
+
+    This is the core helper that eliminates duplication between transaction
+    and span decorators by providing a unified wrapper creation mechanism.
+
+    Parameters
+    ----------
+    func : Callable[P, R]
+        The function to wrap.
+    context_factory : Callable[[], Any]
+        A factory function that creates the Sentry context (span or transaction).
+    is_transaction : bool, optional
+        Whether this is a transaction (affects status setting behavior).
+
+    Returns
+    -------
+    Callable[P, R]
+        The wrapped function.
+    """
+    if asyncio.iscoroutinefunction(func):
+
+        @functools.wraps(func)
+        async def async_wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
+            start_time = time.perf_counter()
+
+            if not sentry_sdk.is_initialized():
+                return await func(*args, **kwargs)
+
+            with context_factory() as context_obj:
+                try:
+                    # Set name for spans (transactions handle this themselves)
+                    if not is_transaction:
+                        safe_set_name(context_obj, func.__qualname__)
+
+                    result = await func(*args, **kwargs)
+                except Exception as e:
+                    _handle_exception_in_sentry_context(context_obj, e)
+                    raise
+                else:
+                    context_obj.set_status("ok")
+                    return result
+                finally:
+                    _finalize_sentry_context(context_obj, start_time)
+
+        return cast(Callable[P, R], async_wrapper)
+
+    @functools.wraps(func)
+    def sync_wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
+        start_time = time.perf_counter()
+
+        if not sentry_sdk.is_initialized():
+            return func(*args, **kwargs)
+
+        with context_factory() as context_obj:
+            try:
+                # Set name for spans (transactions handle this themselves)
+                if not is_transaction:
+                    safe_set_name(context_obj, func.__qualname__)
+
+                result = func(*args, **kwargs)
+            except Exception as e:
+                _handle_exception_in_sentry_context(context_obj, e)
+                raise
+            else:
+                context_obj.set_status("ok")
+                return result
+            finally:
+                _finalize_sentry_context(context_obj, start_time)
+
+    return sync_wrapper
+
+
+# --- Decorators ---
+
+
+def transaction(
+    op: str,
+    name: str | None = None,
+    description: str | None = None,
+) -> Callable[[Callable[P, R]], Callable[P, R]]:
+    """
+    Decorator to wrap a function with a Sentry transaction.
+
+    This handles both synchronous and asynchronous functions automatically.
+    It captures the function's execution time, sets the status to 'ok' on
+    success or 'internal_error' on failure, and records exceptions.
+
+    Parameters
+    ----------
+    op : str
+        The operation name for the transaction (e.g., 'db.query').
+    name : Optional[str]
+        The name for the transaction. Defaults to the function's qualified name.
+    description : Optional[str]
+        A description of what the transaction is doing.
+
+    Returns
+    -------
+    Callable
+        The decorated function.
+    """
+
+    def decorator(func: Callable[P, R]) -> Callable[P, R]:
+        # Early return if Sentry is not initialized to avoid wrapper overhead
+        if not sentry_sdk.is_initialized():
+            return func
+
+        transaction_name = name or f"{func.__module__}.{func.__qualname__}"
+        transaction_description = description or f"Executing {func.__qualname__}"
+
+        def context_factory() -> Any:
+            return sentry_sdk.start_transaction(
+                op=op,
+                name=transaction_name,
+                description=transaction_description,
+            )
+
+        return create_instrumentation_wrapper(func, context_factory, is_transaction=True)
+
+    return decorator
+
+
+def span(op: str, description: str | None = None) -> Callable[[Callable[P, R]], Callable[P, R]]:
+    """
+    Decorator to wrap a function with a Sentry span.
+
+    This should be used on functions called within an existing transaction.
+    It automatically handles both sync and async functions, captures execution
+    time, and records success or failure status.
+
+    Parameters
+    ----------
+    op : str
+        The operation name for the span (e.g., 'db.query.fetch').
+    description : Optional[str]
+        A description of what the span is doing. Defaults to the function's name.
+
+    Returns
+    -------
+    Callable
+        The decorated function.
+    """
+
+    def decorator(func: Callable[P, R]) -> Callable[P, R]:
+        # Early return if Sentry is not initialized to avoid wrapper overhead
+        if not sentry_sdk.is_initialized():
+            return func
+
+        span_description = description or f"Executing {func.__qualname__}"
+
+        def context_factory() -> Any:
+            return sentry_sdk.start_span(op=op, description=span_description)
+
+        return create_instrumentation_wrapper(func, context_factory, is_transaction=False)
+
+    return decorator
+
+
+# --- Context Managers ---
+
+
+@contextmanager
+def start_span(op: str, name: str = "") -> Generator[DummySpan | Any]:
+    """
+    Context manager for creating a Sentry span for a block of code.
+
+    Example:
+        with start_span("db.query", "Fetching user data"):
+            ...
+
+    Parameters
+    ----------
+    op : str
+        The operation name for the span.
+    name : str
+        The name of the span.
+
+    Yields
+    ------
+    Union[DummySpan, sentry_sdk.Span]
+        The Sentry span object or a dummy object if Sentry is not initialized.
+    """
+    start_time = time.perf_counter()
+
+    if not sentry_sdk.is_initialized():
+        # Create a dummy context if Sentry is not available
+        dummy = DummySpan()
+        try:
+            yield dummy
+        finally:
+            pass
+    else:
+        with sentry_sdk.start_span(op=op, name=name) as span:
+            try:
+                yield span
+            finally:
+                span.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
+
+
+@contextmanager
+def start_transaction(op: str, name: str, description: str = "") -> Generator[DummyTransaction | Any]:
+    """
+    Context manager for creating a Sentry transaction for a block of code.
+
+    Example:
+        with start_transaction("task", "process_daily_report"):
+            ...
+
+    Parameters
+    ----------
+    op : str
+        The operation name for the transaction.
+    name : str
+        The name for the transaction.
+    description : str
+        A description of what the transaction is doing.
+
+    Yields
+    ------
+    Union[DummyTransaction, sentry_sdk.Transaction]
+        The Sentry transaction object or a dummy object if Sentry is not initialized.
+    """
+    start_time = time.perf_counter()
+
+    if not sentry_sdk.is_initialized():
+        # Create a dummy context if Sentry is not available
+        dummy = DummyTransaction()
+        try:
+            yield dummy
+        finally:
+            pass
+    else:
+        with sentry_sdk.start_transaction(op=op, name=name, description=description) as transaction:
+            try:
+                yield transaction
+            finally:
+                transaction.set_data("duration_ms", (time.perf_counter() - start_time) * 1000)
+
+
+# --- Enhanced Helper Functions ---
+
+
+def add_tag_to_current_span(key: str, value: Any) -> None:
+    """
+    Add a tag to the current active Sentry span, if it exists.
+
+    This is a convenience function to avoid checking for an active span
+    everywhere in the code.
+
+    Parameters
+    ----------
+    key : str
+        The key of the tag.
+    value : Any
+        The value of the tag.
+    """
+    if sentry_sdk.is_initialized() and (span := sentry_sdk.get_current_span()):
+        span.set_tag(key, value)
+
+
+def add_data_to_current_span(key: str, value: Any) -> None:
+    """
+    Add data to the current active Sentry span, if it exists.
+
+    This is a convenience function to attach arbitrary, non-indexed data
+    to a span for additional context during debugging.
+
+    Parameters
+    ----------
+    key : str
+        The key of the data.
+    value : Any
+        The value of the data.
+    """
+    if sentry_sdk.is_initialized() and (span := sentry_sdk.get_current_span()):
+        span.set_data(key, value)
+
+
+def set_span_attributes(attributes: dict[str, Any]) -> None:
+    """
+    Set multiple tags and data attributes on the current active Sentry span.
+
+    This helper function simplifies attaching context to a span by accepting a
+    dictionary of attributes. Keys are automatically treated as tags.
+
+    Parameters
+    ----------
+    attributes : dict[str, Any]
+        A dictionary where keys are the attribute names and values are the
+        attribute values to set on the span.
+    """
+    if sentry_sdk.is_initialized() and (span := sentry_sdk.get_current_span()):
+        for key, value in attributes.items():
+            span.set_tag(key, value)
+
+
+def set_span_status(status: str, status_map: dict[str, str] | None = None) -> None:
+    """
+    Set status on the current span.
+
+    Parameters
+    ----------
+    status : str
+        The status to set (e.g., "OK", "ERROR", "NOT_FOUND")
+    status_map : dict[str, str] | None, optional
+        A mapping of status keys to Sentry status values. If None, uses default mapping.
+    """
+    if not sentry_sdk.is_initialized():
+        return
+
+    if span := sentry_sdk.get_current_span():
+        # Default status mapping if none provided
+        if status_map is None:
+            status_map = {
+                "OK": "ok",
+                "UNKNOWN": "unknown",
+                "ERROR": "internal_error",
+                "NOT_FOUND": "not_found",
+                "PERMISSION_DENIED": "permission_denied",
+                "INVALID_ARGUMENT": "invalid_argument",
+                "RESOURCE_EXHAUSTED": "resource_exhausted",
+                "UNAUTHENTICATED": "unauthenticated",
+                "CANCELLED": "cancelled",
+            }
+
+        span.set_status(status_map.get(status, status))
+
+
+def set_setup_phase_tag(span: Any, phase: str, status: str = "starting") -> None:
+    """
+    Set a setup phase tag on the span.
+
+    Parameters
+    ----------
+    span : Any
+        The Sentry span to tag
+    phase : str
+        The phase name (e.g., "database", "cogs")
+    status : str
+        The status ("starting" or "finished")
+    """
+    span.set_tag("setup_phase", f"{phase}_{status}")
+
+
+def set_span_error(span: Any, error: Exception, error_type: str = "error") -> None:
+    """
+    Set error information on a span with consistent patterns.
+
+    Parameters
+    ----------
+    span : Any
+        The Sentry span to set error data on
+    error : Exception
+        The exception that occurred
+    error_type : str
+        The type of error (e.g., "error", "discord_error", "db_error")
+    """
+    span.set_status("internal_error")
+    span.set_data(error_type, str(error))
+
+
+def capture_span_exception(exception: Exception, **extra_data: Any) -> None:
+    """
+    Capture an exception in the current span with consistent error handling.
+
+    This consolidates the common pattern of setting span status and data
+    when an exception occurs.
+
+    Parameters
+    ----------
+    exception : Exception
+        The exception to capture.
+    **extra_data : Any
+        Additional data to attach to the span.
+    """
+    if sentry_sdk.is_initialized() and (span := sentry_sdk.get_current_span()):
+        _handle_exception_in_sentry_context(span, exception)
+
+        # Add any additional data
+        for key, value in extra_data.items():
+            span.set_data(f"extra.{key}", value)
+
+
+@contextmanager
+def enhanced_span(op: str, name: str = "", **initial_data: Any) -> Generator[DummySpan | Any]:
+    """
+    Enhanced context manager for creating a Sentry span with initial data.
+
+    This extends the basic start_span with the ability to set initial
+    tags and data, reducing boilerplate in calling code.
+
+    Parameters
+    ----------
+    op : str
+        The operation name for the span.
+    name : str
+        The name for the span.
+    **initial_data : Any
+        Initial data to set on the span.
+
+    Yields
+    ------
+    Union[DummySpan, sentry_sdk.Span]
+        The Sentry span object or a dummy object if Sentry is not initialized.
+    """
+    # Skip spans for very short utility operations in production
+    if not sentry_sdk.is_initialized():
+        yield DummySpan()
+        return
+
+    # In production, skip tracing for certain frequent operations
+    env = initial_data.get("environment", "development")
+    if env not in ("dev", "development") and any(
+        skip_term in name.lower() for skip_term in ["safe_get_attr", "connect_or_create"]
+    ):
+        yield DummySpan()
+        return
+
+    with start_span(op, name) as span:
+        # Set initial data if provided
+        if initial_data:
+            for key, value in initial_data.items():
+                span.set_tag(key, value)
+
+        try:
+            yield span
+        except Exception as e:
+            capture_span_exception(e)
+            raise
+
+
+def instrument_bot_commands(bot: commands.Bot) -> None:
+    """
+    Automatically instruments all bot commands with Sentry transactions.
+
+    This function iterates through all registered commands on the bot and
+    wraps their callbacks with the `@transaction` decorator. This ensures
+    that every command invocation is captured as a Sentry transaction.
+
+    Parameters
+    ----------
+    bot : commands.Bot
+        The instance of the bot whose commands should be instrumented.
+    """
+    # The operation for commands is standardized as `command.run`
+    op = "command.run"
+
+    for command in bot.walk_commands():
+        # The transaction name is the full command name (e.g., "snippet get")
+        transaction_name = f"command.{command.qualified_name}"
+
+        # Apply the transaction decorator to the command's callback
+        original_callback = cast(Callable[..., Coroutine[Any, Any, None]], command.callback)
+        command.callback = transaction(op=op, name=transaction_name)(original_callback)
+
+    logger.info(f"Instrumented {len(list(bot.walk_commands()))} commands with Sentry.")