diff --git a/ddtrace/contrib/openai/patch.py b/ddtrace/contrib/openai/patch.py
index 5e3bf2caead..a610cf55771 100644
--- a/ddtrace/contrib/openai/patch.py
+++ b/ddtrace/contrib/openai/patch.py
@@ -294,7 +294,12 @@ async def patched_endpoint(func, args, kwargs):
             raise
         finally:
             try:
-                g.send((resp, err))
+                if resp is not None:
+                    # openai responses cannot be None
+                    # if resp is None, it is likely because the context
+                    # of the request was cancelled, so we want that to propagate up properly
+                    # see: https://github.com/DataDog/dd-trace-py/issues/10191
+                    g.send((resp, err))
             except StopIteration as e:
                 if err is None:
                     # This return takes priority over `return resp`
diff --git a/releasenotes/notes/openai-async-timeout-errors-f9ccc1adbe4ed14e.yaml b/releasenotes/notes/openai-async-timeout-errors-f9ccc1adbe4ed14e.yaml
new file mode 100644
index 00000000000..17d85525559
--- /dev/null
+++ b/releasenotes/notes/openai-async-timeout-errors-f9ccc1adbe4ed14e.yaml
@@ -0,0 +1,4 @@
+---
+fixes:
+  - |
+    openai: Fixes a bug where `asyncio.TimeoutError`s were not being propagated correctly from canceled OpenAI API requests.
\ No newline at end of file
diff --git a/tests/contrib/openai/test_openai_v1.py b/tests/contrib/openai/test_openai_v1.py
index e14d54bca8d..ec720dfb5d3 100644
--- a/tests/contrib/openai/test_openai_v1.py
+++ b/tests/contrib/openai/test_openai_v1.py
@@ -1682,3 +1682,43 @@ def test_integration_service_name(openai_api_key, ddtrace_run_python_code_in_sub
         assert status == 0, err
         assert out == b""
         assert err == b""
+
+
+async def test_openai_asyncio_cancellation(openai):
+    import asyncio
+
+    import httpx
+
+    class DelayedTransport(httpx.AsyncBaseTransport):
+        def __init__(self, delay: float):
+            self.delay = delay
+            self._transport = httpx.AsyncHTTPTransport()
+
+        async def handle_async_request(self, request: httpx.Request) -> httpx.Response:
+            # Introduce a delay before making the actual request
+            await asyncio.sleep(self.delay)
+            return await self._transport.handle_async_request(request)
+
+    client = openai.AsyncOpenAI(http_client=httpx.AsyncClient(transport=DelayedTransport(delay=10)))
+    asyncio_timeout = False
+
+    try:
+        await asyncio.wait_for(
+            client.chat.completions.create(
+                model="gpt-3.5-turbo",
+                messages=[
+                    {
+                        "role": "user",
+                        "content": "Write a Python program that writes a Python program for a given task.",
+                    },
+                ],
+                user="ddtrace-test",
+            ),
+            timeout=1,
+        )
+    except asyncio.TimeoutError:
+        asyncio_timeout = True
+    except Exception as e:
+        assert False, f"Unexpected exception: {e}"
+
+    assert asyncio_timeout, "Expected asyncio.TimeoutError"