feat: enhance message handling with content pattern matching and update environment configuration

.env.example

@@ -1,2 +1,11 @@
 # Replace with your actual Discord webhook URL
 DISCORD_WEBHOOK_URL=https://discord.com/api/webhooks/<your_webhook_id>/<your_webhook_token>
+
+# Replace with your Discord bot token
+DISCORD_BOT_TOKEN=<your_bot_token>
+
+# Replace with your Discord channel ID
+DISCORD_CHANNEL_ID=<your_channel_id>
+
+# Replace with your Discord guild/server ID
+DISCORD_GUILD_ID=<your_guild_id>

main.py

@@ -50,6 +50,7 @@ logging.basicConfig(
 load_dotenv()
 
 WEBHOOK_URL = os.getenv('DISCORD_WEBHOOK_URL')
+TEST_MESSAGE_DELETE_PATTERN = r"test notification"
 
 
 def get_state() -> dict:
@@ -158,13 +159,16 @@ def create_embed(type: str, tz_list: list[str] | None = None) -> dict:
     return embed
 
 
-def send_notification(message: str) -> None:
+def send_notification(message: str) -> bool:
     """
     Send a notification to the Discord webhook.
+
+    Returns:
+        bool: True when the webhook accepted the notification, False otherwise.
     """
     if not WEBHOOK_URL:
         logging.error("WEBHOOK_URL not set")
-        return
+        return False
 
     _update_state(
         last_type=message,
@@ -192,6 +196,7 @@ def send_notification(message: str) -> None:
             logging.info(f"Notification sent: {message}")
             _update_state(last_success_at=datetime.now(),
                           last_status_code=response.status_code)
+            return True
         else:
             logging.error(
                 f"Failed to send notification: {response.status_code} - "
@@ -199,9 +204,23 @@ def send_notification(message: str) -> None:
             )
             _update_state(last_status_code=response.status_code,
                           last_error=response.text)
+            return False
     except requests.RequestException as e:
         logging.error(f"Error sending notification: {e}")
         _update_state(last_error=str(e))
+        return False
+
+
+def _schedule_startup_test_cleanup(test_sent: bool) -> None:
+    """Schedule one-time cleanup for the startup test notification."""
+    if not test_sent:
+        return
+
+    def cleanup_startup_test_message() -> schedule.CancelJob:
+        delete_old_messages(1, content_pattern=TEST_MESSAGE_DELETE_PATTERN)
+        return schedule.CancelJob
+
+    schedule.every(1).minutes.do(cleanup_startup_test_message)
 
 
 def schedule_notification(interval: str, at: str, type: str) -> None:
@@ -237,10 +256,9 @@ def main() -> None:
 
     logging.info("Scheduler started.")
 
-    # Test the notification on startup
-    send_notification("test")
-    # delete the test message after a short delay to keep the channel clean
-    schedule.every(1).minutes.do(delete_old_messages, 1)
+    # Send one startup test message and cleanup only if send succeeded.
+    test_sent = send_notification("test")
+    _schedule_startup_test_cleanup(test_sent)
 
     # delete old messages on startup to clean up any previous notifications
     # delete_old_messages(6)

maintenance.py

@@ -1,5 +1,6 @@
 import logging
 import os
+import re
 import time
 from datetime import datetime, timedelta
 
@@ -42,15 +43,55 @@ def should_delete_message(
     webhook_id: str,
     author_id: str,
     cutoff: int,
+    content_pattern: str | None = None,
 ) -> bool:
     message_timestamp = int(parse_message_timestamp(message).timestamp())
     return (
         message_timestamp <= cutoff
         and message.get("webhook_id") == webhook_id
         and message.get("author", {}).get("id") == author_id
+        and message_matches_pattern(message, content_pattern)
     )
 
 
+def message_matches_pattern(message: dict, content_pattern: str | None = None) -> bool:
+    """Return True when message content/embed text matches the optional pattern."""
+    if not content_pattern:
+        return True
+
+    text_chunks: list[str] = []
+    content = message.get("content")
+    if isinstance(content, str) and content:
+        text_chunks.append(content)
+
+    embeds = message.get("embeds")
+    if isinstance(embeds, list):
+        for embed in embeds:
+            if not isinstance(embed, dict):
+                continue
+            title = embed.get("title")
+            description = embed.get("description")
+            if isinstance(title, str) and title:
+                text_chunks.append(title)
+            if isinstance(description, str) and description:
+                text_chunks.append(description)
+
+            footer = embed.get("footer")
+            if isinstance(footer, dict):
+                footer_text = footer.get("text")
+                if isinstance(footer_text, str) and footer_text:
+                    text_chunks.append(footer_text)
+
+    if not text_chunks:
+        return False
+
+    searchable_text = "\n".join(text_chunks)
+    try:
+        return re.search(content_pattern, searchable_text, flags=re.IGNORECASE) is not None
+    except re.error:
+        return content_pattern.lower() in searchable_text.lower()
+
+
 def get_rate_limit_retry_after(response: requests.Response) -> float | None:
     header_retry_after = parse_float(response.headers.get("Retry-After"))
     if header_retry_after is not None:
@@ -137,7 +178,7 @@ def find_last_message_by_author(
     return None
 
 
-def fetch_messages_to_delete(headers: dict, channel_id: str, webhook_id: str, author_id: str, cutoff: int, last_message_id: str | None = None) -> tuple[list[dict], str | None]:
+def fetch_messages_to_delete(headers: dict, channel_id: str, webhook_id: str, author_id: str, cutoff: int, last_message_id: str | None = None, content_pattern: str | None = None) -> tuple[list[dict], str | None]:
     """
     Fetch messages from the channel that are older than the cutoff timestamp and sent by the webhook.
     Uses pagination with the 'before' parameter to resume from the last processed message.
@@ -180,6 +221,7 @@ def fetch_messages_to_delete(headers: dict, channel_id: str, webhook_id: str, au
                     webhook_id,
                     author_id,
                     cutoff,
+                    content_pattern,
                 ):
                     delete_list.append(build_delete_entry(message))
 
@@ -240,7 +282,7 @@ def delete_message(headers: dict, channel_id: str, message_id: str) -> tuple[boo
     return False, None, False
 
 
-def delete_old_messages(minutes: int = 6) -> None:
+def delete_old_messages(minutes: int = 6, content_pattern: str | None = None) -> None:
     """
     Delete all messages sent by the webhook in the last `minutes` minutes.
     Uses a dynamic slowdown to avoid hitting Discord API rate limits and pagination to fetch all messages.
@@ -283,6 +325,7 @@ def delete_old_messages(minutes: int = 6) -> None:
         webhook_id,
         author_id,
         cutoff,
+        content_pattern,
     ):
         anchor_message = build_delete_entry(last_author_message)
         deleted, wait_seconds, abort_batch = delete_message(
@@ -303,7 +346,13 @@ def delete_old_messages(minutes: int = 6) -> None:
 
     while True:
         delete_list, next_last_message_id = fetch_messages_to_delete(
-            headers, discord_channel_id, webhook_id, author_id, cutoff, last_message_id
+            headers,
+            discord_channel_id,
+            webhook_id,
+            author_id,
+            cutoff,
+            last_message_id,
+            content_pattern,
         )
 
         if not delete_list:

tests/test_main_scheduler.py

@@ -23,3 +23,101 @@ def test_get_next_scheduled_event():
     nxt = main.get_next_scheduled_event(now)
     assert nxt["type"] == "reminder"
     assert nxt["at"].hour == 11 and nxt["at"].minute == 15
+
+
+def test_schedule_startup_test_cleanup_when_sent(monkeypatch):
+    captured: dict[str, object] = {}
+    delete_calls: list[tuple[int, str | None]] = []
+
+    class FakeEvery:
+        @property
+        def minutes(self):
+            return self
+
+        def do(self, fn, *args, **kwargs):
+            captured["job"] = lambda: fn(*args, **kwargs)
+            return object()
+
+    monkeypatch.setattr(main.schedule, "every", lambda n: FakeEvery())
+    monkeypatch.setattr(
+        main,
+        "delete_old_messages",
+        lambda minutes, content_pattern=None: delete_calls.append(
+            (minutes, content_pattern)),
+    )
+
+    main._schedule_startup_test_cleanup(True)
+
+    assert "job" in captured
+    result = captured["job"]()
+    assert result == main.schedule.CancelJob
+    assert delete_calls == [(1, main.TEST_MESSAGE_DELETE_PATTERN)]
+
+
+def test_schedule_startup_test_cleanup_skips_when_not_sent(monkeypatch):
+    called = {"value": False}
+
+    class FakeEvery:
+        @property
+        def minutes(self):
+            return self
+
+        def do(self, fn, *args, **kwargs):
+            called["value"] = True
+            return object()
+
+    monkeypatch.setattr(main.schedule, "every", lambda n: FakeEvery())
+
+    main._schedule_startup_test_cleanup(False)
+
+    assert called["value"] is False
+
+
+def test_main_sends_startup_test_and_deletes_it(monkeypatch):
+    send_calls: list[str] = []
+    delete_calls: list[tuple[int, str | None]] = []
+    scheduled_jobs: dict[int, list[object]] = {1: [], 5: []}
+
+    monkeypatch.setattr(main, "start_dashboard", lambda: None)
+    monkeypatch.setattr(main, "schedule_notification",
+                        lambda interval, at, type: None)
+
+    class FakeEvery:
+        def __init__(self, minutes_value: int):
+            self.minutes_value = minutes_value
+
+        @property
+        def minutes(self):
+            return self
+
+        def do(self, fn, *args, **kwargs):
+            scheduled_jobs.setdefault(self.minutes_value, []).append(
+                lambda: fn(*args, **kwargs)
+            )
+            return object()
+
+    monkeypatch.setattr(main.schedule, "every", lambda n: FakeEvery(n))
+
+    def fake_send_notification(message: str) -> bool:
+        send_calls.append(message)
+        return True
+
+    def fake_delete_old_messages(minutes: int = 6, content_pattern: str | None = None):
+        delete_calls.append((minutes, content_pattern))
+
+    def fake_run_pending():
+        for job in scheduled_jobs.get(1, []):
+            job()
+        raise KeyboardInterrupt()
+
+    monkeypatch.setattr(main, "send_notification", fake_send_notification)
+    monkeypatch.setattr(main, "delete_old_messages", fake_delete_old_messages)
+    monkeypatch.setattr(main.schedule, "run_pending", fake_run_pending)
+    monkeypatch.setattr(main.time, "sleep", lambda s: None)
+    monkeypatch.setenv("DISCORD_WEBHOOK_URL", "http://example.com/webhook")
+    main.WEBHOOK_URL = "http://example.com/webhook"
+
+    main.main()
+
+    assert send_calls == ["test"]
+    assert delete_calls == [(1, main.TEST_MESSAGE_DELETE_PATTERN)]

tests/test_maintenance.py

@@ -53,6 +53,44 @@ def test_should_delete_message():
     )
 
 
+def test_message_matches_pattern_content_and_embeds():
+    message = {
+        "content": "This is a smoke test payload",
+        "embeds": [
+            {"title": "Reminder", "description": "Half-time in 5 minutes"}
+        ],
+    }
+
+    assert maintenance.message_matches_pattern(message, r"smoke test")
+    assert maintenance.message_matches_pattern(message, r"half-time")
+    assert not maintenance.message_matches_pattern(message, r"does-not-match")
+
+
+def test_should_delete_message_with_content_pattern():
+    ts = int(datetime(2026, 1, 1, 10, 0, 0, tzinfo=timezone.utc).timestamp())
+    message = {
+        "timestamp": "2026-01-01T10:00:00Z",
+        "webhook_id": "w",
+        "author": {"id": "a"},
+        "embeds": [{"description": "This is a test notification."}],
+    }
+
+    assert maintenance.should_delete_message(
+        message,
+        webhook_id="w",
+        author_id="a",
+        cutoff=ts,
+        content_pattern=r"test notification",
+    )
+    assert not maintenance.should_delete_message(
+        message,
+        webhook_id="w",
+        author_id="a",
+        cutoff=ts,
+        content_pattern=r"production-only",
+    )
+
+
 def test_get_rate_limit_retry_after_header_priority():
     response = DummyResponse(
         headers={