diff --git a/distributed/tests/test_cancelled_state.py b/distributed/tests/test_cancelled_state.py
index 9080c1d77f..78bed9e433 100644
--- a/distributed/tests/test_cancelled_state.py
+++ b/distributed/tests/test_cancelled_state.py
@@ -472,10 +472,37 @@ async def test_resumed_cancelled_handle_compute(
     Given the history of a task
     executing -> cancelled -> resumed(fetch)
 
-    A handle_compute should properly restore executing.
+    Setup
+    -----
+    A task is running on the threadpool while a client is cancelling the
+    computations. In this case we cannot cancel the task on the threadpool but
+    need to transition the worker task to cancelled instead. While the task on
+    the threadpool is still running, the client resubmits the graph. This is
+    relatively common in interactive workflows in which a user cancels a
+    computation and resubmits shortly after.
+
+    This resubmission can decide to distribute tasks onto different workers than the initial submission
+
+    Parameters
+    ----------
+    raise_error:
+        Both successful and erred results should be properly handled.
+
+    wait_for_processing:
+        Is the scheduler properly handling the task-done message of the worker
+        even if the task is not, yet, transitioned to processing again?
+
+    Expectation
+    -----------
+    A `handle_compute` should properly restore state `executing` even after the
+    task has transitioned through `cancelled` and `resumed(fetch)`.
+
+
+    See also
+    --------
+    test_worker_state_machine.py::test_executing_cancelled_fetch_executing
+    for minimal example
     """
-    # This test is heavily using set_restrictions to simulate certain scheduler
-    # decisions of placing keys
 
     lock_compute = Lock()
     await lock_compute.acquire()
@@ -515,6 +542,12 @@ async def release_all_futures():
     await release_all_futures()
     await wait_for_state(f3.key, "cancelled", b)
 
+    # At the second iteration, the scheduler chooses to distribute the tasks to
+    # different workers
+    # Particularly for our "stuck" task f3 that is still cancelled(executing) on
+    # worker B this will transition the task to a resumed(fetch) since it is no
+    # longer supposed to be computed on B. However, B will still require the
+    # data of f3 and is supposed to fetch it in case the compute fails
     f1 = c.submit(inc, 1, key="f1", workers=[a.address])
     f2 = c.submit(inc, f1, key="f2", workers=[a.address])
     f3 = c.submit(inc, f2, key="f3", workers=[a.address])
@@ -523,6 +556,9 @@ async def release_all_futures():
     await wait_for_state(f3.key, "resumed", b)
     await release_all_futures()
 
+    # We're again cancelling, forcing f3 to transition back to executing from a
+    # resumed(fetch) state
+
     f1 = c.submit(inc, 1, key="f1", workers=[a.address])
     f2 = c.submit(inc, f1, key="f2", workers=[a.address])
     f3 = c.submit(inc, f2, key="f3", workers=[b.address])
diff --git a/distributed/tests/test_worker_state_machine.py b/distributed/tests/test_worker_state_machine.py
index ae96835605..34b9036fdd 100644
--- a/distributed/tests/test_worker_state_machine.py
+++ b/distributed/tests/test_worker_state_machine.py
@@ -47,6 +47,7 @@
     SerializedTask,
     StateMachineEvent,
     TaskErredMsg,
+    TaskFinishedMsg,
     TaskState,
     TransitionCounterMaxExceeded,
     UnpauseEvent,
@@ -1293,3 +1294,35 @@ def test_gather_dep_failure(ws):
     ]
     assert ws.tasks["x"].state == "error"
     assert ws.tasks["y"].state == "waiting"  # Not ready
+
+
+@pytest.mark.parametrize("fail", [True, False])
+def test_executing_cancelled_fetch_executing(ws, fail):
+    """See also test_cancelled_state.py::test_resumed_cancelled_handle_compute for full example"""
+
+    ws2 = "127.0.0.1:2"
+    instructions = ws.handle_stimulus(
+        ComputeTaskEvent.dummy("x", stimulus_id="s1"),
+        FreeKeysEvent(keys=["x"], stimulus_id="s2"),
+        ComputeTaskEvent.dummy("y", who_has={"x": [ws2]}, stimulus_id="s3"),
+        FreeKeysEvent(keys=["y"], stimulus_id="s4"),
+        ComputeTaskEvent.dummy("x", stimulus_id="s5"),
+    )
+
+    assert len(instructions) == 1
+    assert instructions[0] == Execute(key="x", stimulus_id="s1")
+    if fail:
+        instructions = ws.handle_stimulus(
+            ExecuteFailureEvent.dummy(key="x", stimulus_id="s6")
+        )
+        assert len(instructions) == 1
+        assert isinstance(instructions[0], TaskErredMsg)
+        assert ws.tasks["x"].state == "error"
+
+    else:
+        instructions = ws.handle_stimulus(
+            ExecuteSuccessEvent.dummy(key="x", stimulus_id="s6")
+        )
+        assert len(instructions) == 1
+        assert isinstance(instructions[0], TaskFinishedMsg)
+        assert ws.tasks["x"].state == "memory"