diff --git a/src/openjd/adaptor_runtime/_background/frontend_runner.py b/src/openjd/adaptor_runtime/_background/frontend_runner.py
index d9bd8644..f012acfe 100644
--- a/src/openjd/adaptor_runtime/_background/frontend_runner.py
+++ b/src/openjd/adaptor_runtime/_background/frontend_runner.py
@@ -37,7 +37,11 @@
 _FRONTEND_RUNNER_REQUEST_TIMEOUT: float = 5.0
 
 if OSName.is_windows():
-    from ...adaptor_runtime_client.named_pipe.named_pipe_helper import NamedPipeHelper
+    from ...adaptor_runtime_client.named_pipe.named_pipe_helper import (
+        NamedPipeHelper,
+        NamedPipeTimeoutError,
+        PipeDisconnectedException,
+    )
     import pywintypes
 
 _logger = logging.getLogger(__name__)
@@ -335,6 +339,7 @@ def _send_request(
                 # This is used for aligning to the Linux's behavior in order to reuse the code in handler.
                 # In linux, query string params will always be put in a list.
                 params = {key: [value] for key, value in params.items()}
+            start = time.monotonic()
             try:
                 response = NamedPipeHelper.send_named_pipe_request(
                     self.connection_settings.socket,
@@ -349,8 +354,11 @@ def _send_request(
                     errmsg = f"Received unexpected HTTP status code {status}: {response['body']}"
                     _logger.error(errmsg)
                     raise HTTPError(response, errmsg)
-            except pywintypes.error as e:
-                _logger.error(f"Failed to send {path} request: {e}")
+            # send_named_pipe_request raises its own types for disconnects and timeouts. The elapsed
+            # time shows whether the backend closed the pipe at once or after its read timeout.
+            except (pywintypes.error, PipeDisconnectedException, NamedPipeTimeoutError) as e:
+                elapsed = time.monotonic() - start
+                _logger.error(f"Failed to send {path} request after {elapsed:.2f}s: {e}")
                 raise
             return response
         else:  # pragma: is-windows
diff --git a/test/openjd/adaptor_runtime/unit/background/test_frontend_runner.py b/test/openjd/adaptor_runtime/unit/background/test_frontend_runner.py
index 64736f0a..23f932fa 100644
--- a/test/openjd/adaptor_runtime/unit/background/test_frontend_runner.py
+++ b/test/openjd/adaptor_runtime/unit/background/test_frontend_runner.py
@@ -812,8 +812,12 @@ def test_sends_request(
             mock_read_from_pipe.assert_called_once()
             assert response == json.loads(mock_response)
 
+        @pytest.mark.parametrize(
+            "error_kind", ["pywintypes-error", "pipe-disconnected", "read-timeout"]
+        )
         def test_raises_when_request_fails(
             self,
+            error_kind: str,
             mock_read_from_pipe: MagicMock,
             mock_response: str,
             runner: FrontendRunner,
@@ -821,8 +825,18 @@ def test_raises_when_request_fails(
         ):
             # GIVEN
             import pywintypes
+            from openjd.adaptor_runtime_client.named_pipe.named_pipe_helper import (
+                NamedPipeReadTimeoutError,
+                PipeDisconnectedException,
+            )
 
-            error_instance = pywintypes.error(1, "FunctionName", "An error message")
+            error_instance = {
+                "pywintypes-error": pywintypes.error(1, "FunctionName", "An error message"),
+                "pipe-disconnected": PipeDisconnectedException(
+                    pywintypes.error(109, "ReadFile", "The pipe has been ended.")
+                ),
+                "read-timeout": NamedPipeReadTimeoutError(5.0),
+            }[error_kind]
             mock_read_from_pipe.side_effect = error_instance
             method = "GET"
             path = "/path"
@@ -834,12 +848,15 @@ def test_raises_when_request_fails(
                 with patch.object(
                     frontend_runner.NamedPipeHelper, "establish_named_pipe_connection"
                 ) as mock_establish_named_pipe_connection:
-                    with pytest.raises(pywintypes.error) as raised_exc:
+                    with pytest.raises(type(error_instance)) as raised_exc:
                         runner._send_request(method, path)
 
             # THEN
             assert raised_exc.value is error_instance
-            assert f"Failed to send {path} request: " in caplog.text
+            assert re.search(
+                rf"Failed to send {path} request after \d+\.\d\ds: {re.escape(str(error_instance))}",
+                caplog.text,
+            )
             mock_write_to_pipe.assert_called_once_with(
                 mock_establish_named_pipe_connection(), '{"method": "GET", "path": "/path"}'
             )