fix(proxy): schedule the deprecation loop when a config reload enables alerting

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

litellm/proxy/utils.py

@@ -482,13 +482,20 @@ class ProxyLogging:
             )  # RUN HANGING REQUEST CHECK (if user wants to alert on hanging requests)
             self.hanging_requests_check_started = True
 
-        if (
-            self.alerting is not None
-            and self.slack_alerting_instance is not None
-            and not self.deprecation_check_started
-        ):
-            asyncio.create_task(self.slack_alerting_instance._run_scheduled_deprecation_check())
-            self.deprecation_check_started = True
+        self._ensure_deprecation_check_scheduled()
+
+    def _ensure_deprecation_check_scheduled(self) -> None:
+        """Alerting can be configured at startup or by a later config reload, so schedule from either path"""
+        if self.alerting is None or self.slack_alerting_instance is None or self.deprecation_check_started:
+            return
+
+        try:
+            asyncio.get_running_loop()
+        except RuntimeError:
+            return
+
+        asyncio.create_task(self.slack_alerting_instance._run_scheduled_deprecation_check())
+        self.deprecation_check_started = True
 
     def update_values(
         self,
@@ -517,6 +524,7 @@ class ProxyLogging:
             updated_slack_alerting = True
 
         if updated_slack_alerting is True:
+            self._ensure_deprecation_check_scheduled()
             self.slack_alerting_instance.update_values(
                 alerting=self.alerting,
                 alerting_threshold=self.alerting_threshold,

tests/test_litellm/proxy/utils/proxy_logging/test_lifecycle.py

@@ -144,6 +144,23 @@ async def test_startup_event_schedules_deprecation_check_before_its_alert_type_i
     proxy_logging.slack_alerting_instance._run_scheduled_deprecation_check.assert_called_once_with()
 
 
+@pytest.mark.asyncio
+async def test_update_values_schedules_deprecation_check_when_alerting_arrives_later(proxy_logging):
+    """A proxy that boots without alerting still needs the loop once a config reload turns it on"""
+    proxy_logging.slack_alerting_instance = MagicMock()
+    proxy_logging.slack_alerting_instance.alert_types = []
+    proxy_logging.slack_alerting_instance._run_scheduled_deprecation_check = AsyncMock()
+    proxy_logging._init_litellm_callbacks = MagicMock()
+
+    proxy_logging.startup_event(llm_router=None, redis_usage_cache=None)
+    assert proxy_logging.deprecation_check_started is False
+
+    proxy_logging.update_values(alerting=["slack"])
+
+    assert proxy_logging.deprecation_check_started is True
+    proxy_logging.slack_alerting_instance._run_scheduled_deprecation_check.assert_called_once_with()
+
+
 def test_startup_event_propagates_init_callbacks_failure_raises(proxy_logging):
     proxy_logging.slack_alerting_instance = MagicMock()
     proxy_logging.slack_alerting_instance.alert_types = []