diff --git a/acad.py b/acad.py
index a5ea914..81d7c61 100644
--- a/acad.py
+++ b/acad.py
@@ -213,10 +213,24 @@ def run(self, fn: Callable[[_Acad], Any], timeout: float = 120.0) -> Any:
         try:
             return future.result(timeout=timeout)
         except TimeoutError:
+            # A call still waiting in the queue is withdrawn, so it cannot fire
+            # once AutoCAD is free and duplicate whatever the model sends next.
+            # One already running on the COM thread cannot be stopped.
+            if future.cancel():
+                fate = "The request was not sent to AutoCAD."
+            elif future.done():
+                return future.result()
+            else:
+                fate = (
+                    "The request was already running and may still complete once "
+                    "AutoCAD is free, so check with list_entities before sending "
+                    "it again."
+                )
             raise AcadError(
                 f"AutoCAD did not respond within {timeout:.0f}s. It is most likely "
                 "showing a dialog box or waiting for input at the command line. "
-                "Switch to AutoCAD, press Escape, close any dialog, then retry."
+                "Switch to AutoCAD, press Escape, close any dialog, then retry. "
+                f"{fate}"
             ) from None
 
     def reset(self) -> None:
diff --git a/tests/test_bridge_timeout.py b/tests/test_bridge_timeout.py
new file mode 100644
index 0000000..90de7ec
--- /dev/null
+++ b/tests/test_bridge_timeout.py
@@ -0,0 +1,62 @@
+"""AcadBridge.run gives up on a call without leaving it behind to run later.
+
+All AutoCAD work goes through one COM thread, one call at a time. When AutoCAD
+sits at a dialog, the call in progress hangs, run() times out, and whatever the
+model sends next (usually the same drawing again) queues behind it. Those
+queued calls must not fire once the dialog is closed: their callers were
+already told they failed. Needs no AutoCAD: the calls here never touch COM.
+
+    python -m unittest discover -s tests -t .
+"""
+
+import threading
+import unittest
+
+from acad import AcadBridge, AcadError
+
+
+class BridgeTimeoutTest(unittest.TestCase):
+    def setUp(self):
+        self.bridge = AcadBridge()
+        self.release = threading.Event()
+        self.started = threading.Event()
+
+    def tearDown(self):
+        self.release.set()
+        self.bridge._queue.put((None, None))
+        self.bridge._thread.join(5)
+
+    def _stuck(self, _acad):
+        # Stands in for a COM call blocked behind a modal dialog.
+        self.started.set()
+        self.release.wait(10)
+        return "late"
+
+    def _hold_worker(self):
+        # The stuck call times out for its caller but keeps the COM thread busy.
+        with self.assertRaises(AcadError):
+            self.bridge.run(self._stuck, timeout=0.1)
+        self.assertTrue(self.started.is_set())
+
+    def test_timed_out_call_that_never_started_does_not_run_later(self):
+        self._hold_worker()
+        ran = threading.Event()
+
+        with self.assertRaises(AcadError) as caught:
+            self.bridge.run(lambda _acad: ran.set(), timeout=0.2)
+
+        self.release.set()
+        # Something queued after the timeout still runs, so the worker is alive
+        # and has had its chance to pick up the abandoned call.
+        self.assertEqual(self.bridge.run(lambda _acad: "next", timeout=5), "next")
+        self.assertFalse(ran.is_set(), "the abandoned call ran after its timeout")
+        self.assertIn("was not sent to AutoCAD", str(caught.exception))
+
+    def test_timed_out_call_that_already_started_says_it_may_still_finish(self):
+        with self.assertRaises(AcadError) as caught:
+            self.bridge.run(self._stuck, timeout=0.2)
+        self.assertIn("may still complete", str(caught.exception))
+
+
+if __name__ == "__main__":
+    unittest.main()