diff --git a/tests/v1/core/test_scheduler.py b/tests/v1/core/test_scheduler.py
index aaac2deb12ac..1a705ad827c7 100644
--- a/tests/v1/core/test_scheduler.py
+++ b/tests/v1/core/test_scheduler.py
@@ -1948,6 +1948,84 @@ def test_schedule_skip_tokenizer_init_structured_output_request():
     assert len(scheduler.waiting) == 1
 
 
+def test_kv_connector_finished_sending_race_condition():
+    """
+    Test the race condition where a request is in finished_sending
+    but not actually in a finished state on the scheduler side.
+
+    This can happen when:
+    1. Worker-side NIXL connector times out waiting for decode workers
+    2. Worker reports request in finished_sending to prevent stranding blocks
+    3. Scheduler-side request hasn't reached a finished state yet
+
+    Before the fix, this would crash with AssertionError in _free_blocks.
+    After the fix, it should log a warning and skip block freeing.
+    """
+    from vllm.v1.outputs import KVConnectorOutput
+
+    # Setup scheduler with KV connector
+    scheduler = create_scheduler(
+        enable_prefix_caching=True,
+        use_kv_connector=True,
+    )
+
+    # Create and schedule a request
+    requests = create_requests(num_requests=1, max_tokens=10)
+    request = requests[0]
+    scheduler.add_request(request)
+
+    # Schedule the request
+    scheduler_output = scheduler.schedule()
+    assert len(scheduler_output.scheduled_new_reqs) == 1
+    assert request.request_id in scheduler.requests
+
+    # Simulate model execution - generate one token but DON'T finish
+    model_runner_output = ModelRunnerOutput(
+        req_ids=[request.request_id],
+        req_id_to_index={request.request_id: 0},
+        sampled_token_ids=[[100]],  # One token, not EOS
+        logprobs=None,
+        prompt_logprobs_dict={},
+        pooler_output=[],
+    )
+
+    # Update with this output - request should still be RUNNING
+    scheduler.update_from_output(scheduler_output, model_runner_output)
+    assert request.status == RequestStatus.RUNNING
+    assert len(scheduler.running) == 1
+
+    # Now simulate the race condition: create a KVConnectorOutput that
+    # reports this request as finished_sending, even though the request
+    # is still RUNNING on the scheduler side.
+    # This simulates the timeout scenario in NIXL connector.
+    kv_connector_output = KVConnectorOutput(finished_sending={request.request_id})
+
+    # Schedule again to trigger the race condition
+    scheduler_output2 = scheduler.schedule()
+    model_runner_output2 = ModelRunnerOutput(
+        req_ids=[request.request_id],
+        req_id_to_index={request.request_id: 0},
+        sampled_token_ids=[[101]],  # Another token, not EOS
+        logprobs=None,
+        prompt_logprobs_dict={},
+        pooler_output=[],
+        kv_connector_output=kv_connector_output,
+    )
+
+    # This should handle the race condition gracefully
+    # by logging a warning and skipping block freeing.
+    _ = scheduler.update_from_output(scheduler_output2, model_runner_output2)
+
+    # Verify the request is still in the system and running
+    # (i.e., it was NOT incorrectly freed)
+    assert request.request_id in scheduler.requests
+    assert request.status == RequestStatus.RUNNING
+    assert len(scheduler.running) == 1
+
+    # The request should NOT have been freed
+    assert request.request_id not in scheduler.finished_req_ids
+
+
 def test_priority_scheduling_preemption_and_resumption_when_out_of_kv():
     """Test that priority scheduling preempts lower priority requests
     when out of KV cache space."""
diff --git a/vllm/v1/core/sched/scheduler.py b/vllm/v1/core/sched/scheduler.py
index 08368b7d99ef..387145372e86 100644
--- a/vllm/v1/core/sched/scheduler.py
+++ b/vllm/v1/core/sched/scheduler.py
@@ -1365,8 +1365,24 @@ def _update_from_kv_xfer_finished(self, kv_connector_output: KVConnectorOutput):
             self.finished_recving_kv_req_ids.add(req_id)
         for req_id in kv_connector_output.finished_sending or ():
             logger.debug("Finished sending KV transfer for request %s", req_id)
-            assert req_id in self.requests
-            self._free_blocks(self.requests[req_id])
+            request = self.requests.get(req_id)
+            if request is None:
+                logger.warning(
+                    "Got finished sending KV transfer for request %s, "
+                    "but the request is already freed.",
+                    req_id,
+                )
+            elif not request.is_finished():
+                logger.warning(
+                    "Got finished sending KV transfer for request %s, "
+                    "but the request is not finished (status=%s). "
+                    "This may indicate the request was aborted or the KV "
+                    "transfer timed out before the request completed.",
+                    req_id,
+                    request.status,
+                )
+            else:
+                self._free_blocks(request)
 
     def _update_requests_with_invalid_blocks(
         self, requests: Iterable[Request], invalid_block_ids: set[int]