diff --git a/tests/integration/sdk/test_sync_stream_connection_release_wire.py b/tests/integration/sdk/test_sync_stream_connection_release_wire.py
index a8b49d285c3..21774df66d0 100644
--- a/tests/integration/sdk/test_sync_stream_connection_release_wire.py
+++ b/tests/integration/sdk/test_sync_stream_connection_release_wire.py
@@ -212,3 +212,36 @@ def test_sync_stream_that_raises_mid_stream_releases_the_connection() -> None:
         assert _open_sessions_settling_to(wire, at_most=0) == 0, (
             "a stream that raised mid-way left its TCP session open"
         )
+
+
+_STUCK: Final = _Shape(
+    "hosted_vllm",
+    "hosted_vllm/stuck-model",
+    _OPENAI_OPENING,
+    (_openai_delta("the model is stuck on this", None),) * (10 * litellm.REPEATED_STREAMING_CHUNK_LIMIT),
+)
+
+
+def _still_generating_peer(request: Request) -> Reply:
+    return Reply(content_type="text/event-stream", chunks=(_STUCK.opening, *_STUCK.closing), pause_between_chunks=0.01)
+
+
+def test_sync_stream_stuck_repeating_one_chunk_releases_the_connection() -> None:
+    with wire_server(_still_generating_peer, keep_alive=True) as wire:
+        stuck: Final = litellm.completion(**_request_kwargs(_STUCK, wire))
+        with pytest.raises(Exception, match="repeating the same chunk"):
+            for _ in stuck:
+                pass
+        assert _open_sessions_settling_to(wire, at_most=0) == 0, "a stream stuck on one chunk left its TCP session open"
+
+
+@pytest.mark.asyncio
+async def test_async_stream_stuck_repeating_one_chunk_releases_the_connection() -> None:
+    with wire_server(_still_generating_peer, keep_alive=True) as wire:
+        stuck: Final = await litellm.acompletion(**_request_kwargs(_STUCK, wire))
+        with pytest.raises(Exception, match="repeating the same chunk"):
+            async for _ in stuck:
+                pass
+        assert await _open_sessions_settling_to_while_the_loop_runs(wire, at_most=0) == 0, (
+            "a stream stuck on one chunk left its TCP session open"
+        )
diff --git a/tests/unit/litellm_core_utils/test_streaming_handler.py b/tests/unit/litellm_core_utils/test_streaming_handler.py
index db08191e18c..19f971a5f37 100644
--- a/tests/unit/litellm_core_utils/test_streaming_handler.py
+++ b/tests/unit/litellm_core_utils/test_streaming_handler.py
@@ -2741,7 +2741,7 @@ _STUCK_PROVIDER_CHUNK_CAP: Final = 10 * litellm.REPEATED_STREAMING_CHUNK_LIMIT
 
 class _StuckProvider:
     def __init__(self) -> None:
-        self.closed = threading.Event()
+        self.closed_early = threading.Event()
         self.chunks_sent = 0
 
     def _next_chunk(self) -> ModelResponseStream:
@@ -2751,15 +2751,17 @@ class _StuckProvider:
     def sync_stream(self) -> Iterator[ModelResponseStream]:
         try:
             yield from (self._next_chunk() for _ in range(_STUCK_PROVIDER_CHUNK_CAP))
-        finally:
-            self.closed.set()
+        except GeneratorExit:
+            self.closed_early.set()
+            raise
 
     async def async_stream(self) -> AsyncIterator[ModelResponseStream]:
         try:
             for _ in range(_STUCK_PROVIDER_CHUNK_CAP):
                 yield self._next_chunk()
-        finally:
-            self.closed.set()
+        except GeneratorExit:
+            self.closed_early.set()
+            raise
 
 
 class _FailureRecorder(CustomLogger):
@@ -2786,7 +2788,7 @@ def _stuck_stream_wrapper(
         messages=[{"role": "user", "content": "hi"}],
         stream=True,
         call_type=call_type,
-        start_time=datetime.datetime.now(),
+        start_time=datetime.datetime(2026, 1, 1),
         litellm_call_id=f"stuck-stream-{call_type}",
         function_id=f"stuck-stream-{call_type}",
         dynamic_failure_callbacks=[recorder],
@@ -2815,7 +2817,8 @@ async def test_async_stream_stuck_on_one_chunk_closes_the_provider_stream_and_lo
     with pytest.raises(Exception, match="repeating the same chunk"):
         async for _ in wrapper:
             pass
-    assert provider.closed.is_set()
+    assert provider.closed_early.is_set()
+    assert provider.chunks_sent <= litellm.REPEATED_STREAMING_CHUNK_LIMIT + 1
     chunks_sent_at_failure: Final = provider.chunks_sent
 
     with pytest.raises(StopAsyncIteration):
@@ -2836,7 +2839,8 @@ def test_sync_stream_stuck_on_one_chunk_closes_the_provider_stream_and_logs_one_
     with pytest.raises(Exception, match="repeating the same chunk"):
         for _ in wrapper:
             pass
-    assert provider.closed.is_set()
+    assert provider.closed_early.is_set()
+    assert provider.chunks_sent <= litellm.REPEATED_STREAMING_CHUNK_LIMIT + 1
     chunks_sent_at_failure: Final = provider.chunks_sent
     assert "repeating the same chunk" in recorder.failures.get(timeout=5)