Add Sentry log filtering to reduce noise in error reporting

- Added detailed bot state information to error messages when sending fails.
- Implemented early validation of bot readiness and closure in `send_to_discord`.
- Introduced `safe_send_to_discord` to manage bot state issues and prevent '_MissingSentinel' errors.
- Improved logging for better debugging of bot state and HTTP client status.

discord_reminder_bot/main.py

@@ -1,8 +1,10 @@
 from __future__ import annotations
 
+import asyncio
 import datetime
 import json
 import os
+import platform
 import sys
 import tempfile
 from functools import partial
@@ -23,6 +25,9 @@ from discord.abc import PrivateChannel
 from discord.utils import escape_markdown
 from discord_webhook import DiscordWebhook
 from loguru import logger
+from sentry_sdk.integrations.asyncio import AsyncioIntegration
+from sentry_sdk.integrations.loguru import LoggingLevels, LoguruIntegration
+from sentry_sdk.integrations.sys_exit import SysExitIntegration
 
 from discord_reminder_bot.helpers import calculate, generate_markdown_state, generate_state, get_human_readable_time, parse_time
 from discord_reminder_bot.modals import CronReminderModifyModal, DateReminderModifyModal, IntervalReminderModifyModal
@@ -36,6 +41,7 @@ if TYPE_CHECKING:
     from discord.guild import GuildChannel
     from discord.interactions import InteractionChannel
     from requests import Response
+    from sentry_sdk.types import Hint, Log
 
 
 def my_listener(event: JobExecutionEvent) -> None:
@@ -64,15 +70,25 @@ def my_listener(event: JobExecutionEvent) -> None:
         send_webhook(custom_url="", message=msg)
 
     if event.exception:
-        with sentry_sdk.push_scope() as scope:
+        with sentry_sdk.new_scope() as scope:
             scope.set_extra("job_id", event.job_id)
             scope.set_extra("scheduled_run_time", event.scheduled_run_time.isoformat() if event.scheduled_run_time else "None")
             scope.set_extra("event_code", event.code)
+            scope.set_extra("bot_is_ready", bot.is_ready() if "bot" in globals() else "Unknown")
+            scope.set_extra("bot_is_closed", bot.is_closed() if "bot" in globals() else "Unknown")
             sentry_sdk.capture_exception(event.exception)
 
+        # Create detailed error message with bot state information
+        bot_state_info = ""
+        if "bot" in globals():
+            bot_state_info = f"\nBot State: ready={bot.is_ready()}, closed={bot.is_closed()}, user={bot.user}"
+            if hasattr(bot, "http") and bot.http:
+                global_over = getattr(bot.http, "_global_over", None)
+                bot_state_info += f"\nHTTP State: _global_over type={type(global_over)}"
+
         send_webhook(
             custom_url="",
-            message=f"discord-reminder-bot failed to send message to Discord\n{event.exception}\n{event.traceback}",
+            message=f"discord-reminder-bot failed to send message to Discord\nJob ID: {event.job_id}\nScheduled Time: {event.scheduled_run_time.isoformat() if event.scheduled_run_time else 'None'}{bot_state_info}\n{event.exception}\n{event.traceback}",
         )
 
 
@@ -91,7 +107,16 @@ class RemindBotClient(discord.Client):
     async def on_error(self, event_method: str, *args: list[Any], **kwargs: dict[str, Any]) -> None:
         """Log errors that occur in the bot."""
         logger.exception(f"An error occurred in {event_method} with args: {args} and kwargs: {kwargs}")
-        sentry_sdk.capture_exception()  # TODO(TheLovinator): Add more context to the error  # noqa: TD003
+
+        with sentry_sdk.new_scope() as scope:
+            scope.set_extra("event_method", event_method)
+            scope.set_extra("args", args)
+            scope.set_extra("kwargs", kwargs)
+            scope.set_extra("bot_is_ready", self.is_ready())
+            scope.set_extra("bot_is_closed", self.is_closed())
+            if hasattr(self, "ws") and self.ws:
+                scope.set_extra("session_id", self.ws.session_id)
+            sentry_sdk.capture_exception()
 
     async def on_ready(self) -> None:
         """Called when the client is done preparing the data received from Discord. Usually after login is successful and the Client.guilds and co. are filled up.
@@ -113,6 +138,45 @@ class RemindBotClient(discord.Client):
 
     async def setup_hook(self) -> None:
         """Setup the bot."""
+        default_sentry_dsn: str = "https://c4c61a52838be9b5042144420fba5aaa@o4505228040339456.ingest.us.sentry.io/4508707268984832"
+
+        def before_send_log(log: Log, _hint: Hint) -> Log | None:
+            """Filter out unwanted log messages before sending to Sentry.
+
+            Args:
+                log: The log object containing message and metadata.
+                _hint: Additional context about the log.
+
+            Returns:
+                The log object if it should be sent to Sentry, None to discard it.
+            """
+            ignored_log_messages: list[str] = [
+                "has connected to Gateway",
+                "has successfully RESUMED session",
+            ]
+
+            if log.get("body") and any(noisy_log in log["body"] for noisy_log in ignored_log_messages):
+                return None
+
+            return log
+
+        sentry_sdk.init(
+            dsn=os.getenv("SENTRY_DSN", default_sentry_dsn),
+            environment=platform.node() or "Unknown",
+            traces_sample_rate=1.0,
+            profile_session_sample_rate=1.0,
+            send_default_pii=True,
+            _experiments={
+                "enable_logs": True,
+                "before_send_log": before_send_log,
+            },
+            integrations=[
+                AsyncioIntegration(),
+                LoguruIntegration(sentry_logs_level=LoggingLevels.WARNING.value),
+                SysExitIntegration(capture_successful_exits=True),
+            ],
+        )
+
         scheduler.add_listener(my_listener, EVENT_JOB_MISSED | EVENT_JOB_ERROR)
         jobs: list[Job] = scheduler.get_jobs()
         if jobs:
@@ -1217,19 +1281,62 @@ async def send_to_discord(channel_id: int, message: str, author_id: int) -> None
         channel_id: The Discord channel ID.
         message: The message.
         author_id: User we should mention in the message.
+
+    Raises:
+        RuntimeError: If the bot is not ready or is closed.
     """
     logger.info(f"Sending message to channel '<#{channel_id}>' with message: '{message}'")
 
-    channel: GuildChannel | discord.Thread | PrivateChannel | None = bot.get_channel(channel_id)
+    # Wait 3 seconds to ensure the bot is ready
-    if channel is None:
+    logger.debug("Waiting for 3 seconds to ensure the bot is ready before sending the message.")
-        channel = await bot.fetch_channel(channel_id)
+    await asyncio.sleep(3)
+
+    # Early validation of bot state
+    if not bot.is_ready():
+        error_msg = f"Bot is not ready! Cannot send message to channel {channel_id}\nMessage: {message}\nAuthor ID: {author_id}"
+        logger.error(error_msg)
+        raise RuntimeError(error_msg)
+
+    if bot.is_closed():
+        error_msg = f"Bot is closed! Cannot send message to channel {channel_id}\nMessage: {message}\nAuthor ID: {author_id}"
+        logger.error(error_msg)
+        raise RuntimeError(error_msg)
+
+    # Debug bot state before attempting to fetch channel
+    _debug_bot_state()
+
+    try:
+        channel: GuildChannel | discord.Thread | PrivateChannel | None = bot.get_channel(channel_id)
+        logger.debug(f"bot.get_channel({channel_id}) returned: {channel}")
+
+        if channel is None:
+            logger.info(f"Channel {channel_id} not in cache, attempting to fetch from API")
+            channel = await bot.fetch_channel(channel_id)
+            logger.debug(f"bot.fetch_channel({channel_id}) returned: {channel}")
+    except Exception as e:
+        logger.error(f"Failed to get/fetch channel {channel_id}: {type(e).__name__}: {e}")
+        logger.error(f"Bot state during error - is_ready: {bot.is_ready()}, is_closed: {bot.is_closed()}")
+        raise
 
     # Channels we can't send messages to
     if isinstance(channel, discord.ForumChannel | discord.CategoryChannel | PrivateChannel):
-        logger.warning(f"We haven't implemented sending messages to this channel type {type(channel)}")
+        logger.error(f"We haven't implemented sending messages to this channel type {type(channel)}")
         return
 
-    await channel.send(f"<@{author_id}>\n{message}")
+    try:
+        logger.debug(f"Attempting to send message to channel {channel} (type: {type(channel)})")
+        message_content = f"<@{author_id}>\n{message}"
+        logger.debug(f"Message content length: {len(message_content)} characters")
+
+        sent_message = await channel.send(message_content)
+        logger.info(f"Successfully sent message to channel {channel_id}, message ID: {sent_message.id}")
+    except Exception as e:
+        logger.error(f"Failed to send message to channel {channel_id}: {type(e).__name__}: {e}")
+        logger.error(f"Channel: {channel}, Channel type: {type(channel)}")
+        logger.error(f"Bot state during send error - is_ready: {bot.is_ready()}, is_closed: {bot.is_closed()}")
+        if hasattr(channel, "guild"):
+            logger.error(f"Guild: {channel.guild}, Guild available: {getattr(channel.guild, 'available', 'Unknown')}")
+        raise
 
 
 async def send_to_user(user_id: int, guild_id: int, message: str) -> None:
@@ -1272,6 +1379,31 @@ async def send_to_user(user_id: int, guild_id: int, message: str) -> None:
         logger.exception(f"Failed to send message '{message}' to user '{user_id}' in guild '{guild_id}'")
 
 
+def _debug_bot_state() -> None:
+    """Debug helper function to log bot state information."""
+    logger.debug(f"Bot is_ready: {bot.is_ready()}")
+    logger.debug(f"Bot is_closed: {bot.is_closed()}")
+    logger.debug(f"Bot user: {bot.user}")
+    logger.debug(f"Bot guilds count: {len(bot.guilds) if bot.guilds else 'None'}")
+
+    # Check bot's http client state
+    if hasattr(bot, "http") and bot.http:
+        logger.debug(f"Bot HTTP client state: connector_initialized={hasattr(bot.http, 'connector')}")
+        try:
+            # Safely check _global_over attribute which is causing the error
+            global_over = getattr(bot.http, "_global_over", None)
+            logger.debug(f"Bot HTTP _global_over type: {type(global_over)}")
+            logger.debug(f"Bot HTTP _global_over: {global_over}")
+            if global_over is not None and hasattr(global_over, "is_set"):
+                logger.debug(f"Bot HTTP _global_over.is_set(): {global_over.is_set()}")
+            else:
+                logger.warning("Bot HTTP _global_over missing is_set method - this is likely the cause of the error")
+        except (AttributeError, TypeError) as debug_error:
+            logger.warning(f"Could not inspect bot HTTP _global_over: {debug_error}")
+    else:
+        logger.error("Bot HTTP client is None or missing")
+
+
 if __name__ == "__main__":
     bot_token: str = os.getenv("BOT_TOKEN", default="")
     if not bot_token:
@@ -1280,3 +1412,4 @@ if __name__ == "__main__":
 
     logger.info("Starting bot.")
     bot.run(bot_token)
+    logger.info("Bot has been stopped.")

discord_reminder_bot/settings.py

@@ -1,12 +1,10 @@
 from __future__ import annotations
 
 import os
-import platform
 from pathlib import Path
 from zoneinfo import ZoneInfo, ZoneInfoNotFoundError
 
 import pytz
-import sentry_sdk
 from apscheduler.jobstores.sqlalchemy import SQLAlchemyJobStore
 from apscheduler.schedulers.asyncio import AsyncIOScheduler
 from dotenv import load_dotenv
@@ -16,14 +14,6 @@ from discord_reminder_bot.helpers import generate_state
 
 load_dotenv(verbose=True)
 
-default_sentry_dsn: str = "https://c4c61a52838be9b5042144420fba5aaa@o4505228040339456.ingest.us.sentry.io/4508707268984832"
-sentry_sdk.init(
-    dsn=os.getenv("SENTRY_DSN", default_sentry_dsn),
-    environment=platform.node() or "Unknown",
-    traces_sample_rate=1.0,
-    send_default_pii=True,
-)
-
 
 def get_scheduler() -> AsyncIOScheduler:
     """Return the scheduler instance.

uv.lock

@@ -25,7 +25,7 @@ wheels = [
 
 [[package]]
 name = "aiohttp"
-version = "3.12.13"
+version = "3.12.14"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "aiohappyeyeballs" },
@@ -36,25 +36,25 @@ dependencies = [
     { name = "propcache" },
     { name = "yarl" },
 ]
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