diff --git a/tests/distributed/omni_connectors/test_chunk_transfer_adapter.py b/tests/distributed/omni_connectors/test_chunk_transfer_adapter.py
index c72cc91d0..8fb6278c1 100644
--- a/tests/distributed/omni_connectors/test_chunk_transfer_adapter.py
+++ b/tests/distributed/omni_connectors/test_chunk_transfer_adapter.py
@@ -591,6 +591,25 @@ def test_save_async_drops_late_previous_segment_after_boundary_reset(build_adapt
     assert adapter._pending_save_reqs[-1]["request"] is next_segment
 
 
+def test_send_single_request_drops_queued_old_segment_after_boundary(build_adapter):
+    adapter, connector = build_adapter(stage_id=1)
+    adapter.custom_process_next_stage_input_func = lambda **kwargs: OmniPayloadStruct(meta=MetaStruct())
+    request = _req("req-queued-old", RequestStatus.WAITING, external_req_id="ext-queued-old")
+    request.resumable = True
+    request._omni_segment_generation = 0
+
+    adapter.save_async(multimodal_output=None, request=request, is_segment_finished=False)
+    adapter.save_async(multimodal_output=None, request=request, is_segment_finished=True)
+
+    old_task = adapter._pending_save_reqs.popleft()
+    adapter._send_single_request(old_task)
+    connector.put.assert_not_called()
+
+    boundary_task = adapter._pending_save_reqs.popleft()
+    adapter._send_single_request(boundary_task)
+    connector.put.assert_called_once()
+
+
 def test_send_single_request_cleans_up_after_finished_payload(build_adapter, monkeypatch):
     adapter, _ = build_adapter(stage_id=1)
     request = _req("req-finished", RequestStatus.FINISHED_STOPPED, external_req_id="ext-finished")
diff --git a/vllm_omni/distributed/omni_connectors/transfer_adapter/chunk_transfer_adapter.py b/vllm_omni/distributed/omni_connectors/transfer_adapter/chunk_transfer_adapter.py
index 7c9267162..7668fa5a0 100644
--- a/vllm_omni/distributed/omni_connectors/transfer_adapter/chunk_transfer_adapter.py
+++ b/vllm_omni/distributed/omni_connectors/transfer_adapter/chunk_transfer_adapter.py
@@ -370,6 +370,21 @@ class OmniChunkTransferAdapter(OmniTransferAdapterBase):
         stage_id = self.connector.stage_id
         next_stage_id = stage_id + 1
         external_req_id = request.external_req_id
+        task_generation = task.get("segment_generation")
+        expected_generation = self._segment_generation.get(external_req_id, task_generation)
+        if (
+            isinstance(task_generation, int)
+            and isinstance(expected_generation, int)
+            and task_generation < expected_generation
+            and not is_segment_finished
+        ):
+            logger.warning(
+                "Skip queued late chunk for request %s, segment_generation=%s, expected=%s",
+                external_req_id,
+                task_generation,
+                expected_generation,
+            )
+            return
         chunk_id = self.put_req_chunk[external_req_id]
         connector_put_key = f"{external_req_id}_{stage_id}_{chunk_id}"
         # Process payload in save_loop thread