diff --git a/airflow-core/src/airflow/api_fastapi/execution_api/app.py b/airflow-core/src/airflow/api_fastapi/execution_api/app.py
index f10c772e03f47..049fc60bdab78 100644
--- a/airflow-core/src/airflow/api_fastapi/execution_api/app.py
+++ b/airflow-core/src/airflow/api_fastapi/execution_api/app.py
@@ -253,9 +253,25 @@ async def _extract_w3c_trace_context(
     token = otel_context.attach(ctx)
     try:
         yield
-    finally:
+    except GeneratorExit:
+        # Cross-task force-close (client disconnect / request cancellation): the
+        # finalizer runs in a different asyncio Task — and thus a different
+        # contextvars.Context — than attach did, so detaching the token would raise
+        # "Token was created in a different Context" (which OTel logs at ERROR before
+        # any suppression here could see it). The attached Context is being discarded
+        # with the dying task, so detaching is unnecessary; skip it and re-raise.
+        raise
+    except BaseException:
+        # A route handler raised: FastAPI throws the exception into this generator at
+        # the yield, in the SAME task that attach ran in. Detach so the upstream trace
+        # context does not stay attached for the exception handler, the error response,
+        # and any spans/logs emitted while unwinding. Suppress any detach error so it
+        # cannot mask the original exception being propagated.
         with contextlib.suppress(Exception):
             otel_context.detach(token)
+        raise
+    else:
+        otel_context.detach(token)
 
 
 def _inject_trace_context_dep(routes, mode: str) -> None:
diff --git a/airflow-core/tests/unit/api_fastapi/execution_api/test_app.py b/airflow-core/tests/unit/api_fastapi/execution_api/test_app.py
index 0a71e65525505..5f90c5a9b83eb 100644
--- a/airflow-core/tests/unit/api_fastapi/execution_api/test_app.py
+++ b/airflow-core/tests/unit/api_fastapi/execution_api/test_app.py
@@ -26,7 +26,10 @@
 from fastapi.testclient import TestClient
 from opentelemetry import context as otel_context, propagate as otel_propagate
 
-from airflow.api_fastapi.execution_api.app import create_task_execution_api_app
+from airflow.api_fastapi.execution_api.app import (
+    _extract_w3c_trace_context,
+    create_task_execution_api_app,
+)
 from airflow.api_fastapi.execution_api.datamodels.taskinstance import TaskInstance
 from airflow.api_fastapi.execution_api.datamodels.token import TIClaims, TIToken
 from airflow.api_fastapi.execution_api.security import require_auth
@@ -244,3 +247,47 @@ async def mock_require_auth(request: Request) -> TIToken:
         ):
             with pytest.raises(RuntimeError, match="boom"):
                 test_client.get("/variables/k", headers={"Authorization": "Bearer fake"})
+
+    @staticmethod
+    def _make_request() -> Request:
+        return Request({"type": "http", "headers": []})
+
+    @pytest.mark.asyncio
+    async def test_detach_skipped_on_generator_exit(self):
+        """A force-closed generator (aclose -> GeneratorExit) must NOT call detach.
+
+        On a real client disconnect the generator is finalised from a different asyncio
+        Task, where detach would raise "Token was created in a different Context". Closing
+        from the same task (as here) does not reproduce that cross-context error, but it
+        does exercise the GeneratorExit branch and asserts detach is skipped on it.
+        """
+        with mock.patch.object(otel_context, "detach") as detach_spy:
+            gen = _extract_w3c_trace_context(self._make_request(), dependency_solver="fastapi")
+            await gen.asend(None)  # run up to and including the yield (after attach)
+            await gen.aclose()  # raises GeneratorExit at the yield
+
+        detach_spy.assert_not_called()
+
+    @pytest.mark.asyncio
+    async def test_detach_runs_on_route_exception(self):
+        """A route handler error (athrow at the yield) runs in the same task, so detach
+        must run -- otherwise the upstream trace context leaks into the error handling.
+        """
+        with mock.patch.object(otel_context, "detach") as detach_spy:
+            gen = _extract_w3c_trace_context(self._make_request(), dependency_solver="fastapi")
+            await gen.asend(None)  # run up to the yield
+            with pytest.raises(RuntimeError, match="boom"):
+                await gen.athrow(RuntimeError("boom"))  # FastAPI's route-error finalization
+
+        detach_spy.assert_called_once()
+
+    @pytest.mark.asyncio
+    async def test_detach_runs_on_normal_completion(self):
+        """Normal completion still detaches the token in the request's own Context."""
+        with mock.patch.object(otel_context, "detach") as detach_spy:
+            gen = _extract_w3c_trace_context(self._make_request(), dependency_solver="fastapi")
+            await gen.asend(None)  # run up to the yield
+            with pytest.raises(StopAsyncIteration):
+                await gen.asend(None)  # resume past the yield -> else branch -> detach
+
+        detach_spy.assert_called_once()