diff --git a/litellm/litellm_core_utils/logging_worker.py b/litellm/litellm_core_utils/logging_worker.py
index 59f0ee0d7ec..cb0baa82767 100644
--- a/litellm/litellm_core_utils/logging_worker.py
+++ b/litellm/litellm_core_utils/logging_worker.py
@@ -143,14 +143,18 @@ class LoggingWorker:
     def _close_queued_coroutines(self) -> None:
         if self._queue is None:
             return
-        while True:
-            try:
-                logging_task: Final = self._queue.get_nowait()
-            except asyncio.QueueEmpty:
-                return
+        while (logging_task := self._dequeue_task()) is not None:
             logging_task["coroutine"].close()
             self._queue.task_done()
 
+    def _dequeue_task(self) -> LoggingTask | None:
+        if self._queue is None:
+            return None
+        try:
+            return self._queue.get_nowait()
+        except asyncio.QueueEmpty:
+            return None
+
     def _release_running_tasks(self) -> None:
         for task in tuple(self._running_tasks):
             if not task.done():
@@ -158,7 +162,7 @@ class LoggingWorker:
                     task.cancel()
                 except RuntimeError:
                     pass
-                setattr(task, "_log_destroy_pending", False)
+                task._log_destroy_pending = False  # pyright: ignore[reportPrivateUsage, reportAttributeAccessIssue]  # asyncio private shutdown flag
             if coroutine := self._task_coroutines.get(task):
                 coroutine.close()
         self._running_tasks.clear()
@@ -280,6 +284,7 @@ class LoggingWorker:
 
         try:
             self._queue.put_nowait(task)
+            self._start_queued_tasks()
         except asyncio.QueueFull:
             # Still full - handle it appropriately (clear or retry again)
             self._handle_queue_full(task)
diff --git a/tests/test_litellm/litellm_core_utils/test_logging_worker.py b/tests/test_litellm/litellm_core_utils/test_logging_worker.py
index 74bba4b3ec8..af419ea6efe 100644
--- a/tests/test_litellm/litellm_core_utils/test_logging_worker.py
+++ b/tests/test_litellm/litellm_core_utils/test_logging_worker.py
@@ -184,9 +184,10 @@ class TestLoggingWorker:
     @pytest.mark.asyncio
     async def test_clear_queue_with_time_limit(self, logging_worker):
         """Test that clear_queue respects the time limit."""
+
         # Create several mock coroutines that take time to complete
-        slow_coro = AsyncMock()
-        slow_coro.return_value = asyncio.sleep(0.5)  # Takes 500ms
+        async def slow_coro() -> None:
+            await asyncio.sleep(0.5)
 
         # Initialize the worker and add items
         logging_worker._ensure_queue()
@@ -388,6 +389,25 @@ class TestLoggingWorker:
 
         assert len(processed) >= 4, f"Expected 4+ tasks processed, got {len(processed)}"
 
+    @pytest.mark.asyncio
+    async def test_delayed_enqueue_retry_restarts_workers_after_queue_drains(self):
+        worker = LoggingWorker(timeout=1.0, max_queue_size=1, concurrency=1)
+        worker.start()
+        processed = asyncio.Event()
+
+        async def retried_task() -> None:
+            processed.set()
+
+        try:
+            await worker._retry_enqueue_task(
+                {"coroutine": retried_task(), "context": contextvars.copy_context()},
+                0.0,
+            )
+
+            await asyncio.wait_for(processed.wait(), timeout=1.0)
+        finally:
+            await worker.stop()
+
     @pytest.mark.asyncio
     async def test_event_loop_change_handling(self):
         """Test that LoggingWorker handles event loop changes correctly.