diff --git a/examples/debugging/root_self_cancelled_w_error.py b/examples/debugging/root_self_cancelled_w_error.py
new file mode 100644
index 00000000..b3c15288
--- /dev/null
+++ b/examples/debugging/root_self_cancelled_w_error.py
@@ -0,0 +1,35 @@
+import trio
+import tractor
+
+
+async def main():
+    async with tractor.open_root_actor(
+        debug_mode=True,
+        loglevel='cancel',
+    ) as _root:
+
+        # manually trigger self-cancellation and wait
+        # for it to fully trigger.
+        _root.cancel_soon()
+        await _root._cancel_complete.wait()
+        print('root cancelled')
+
+        # now ensure we can still use the REPL
+        try:
+            await tractor.pause()
+        except trio.Cancelled as _taskc:
+            assert (root_cs := _root._root_tn.cancel_scope).cancel_called
+            # NOTE^^ above logic but inside `open_root_actor()` and
+            # passed to the `shield=` expression is effectively what
+            # we're testing here!
+            await tractor.pause(shield=root_cs.cancel_called)
+
+        # XXX, if shield logic *is wrong* inside `open_root_actor()`'s
+        # crash-handler block this should never be interacted,
+        # instead `trio.Cancelled` would be bubbled up: the original
+        # BUG.
+        assert 0
+
+
+if __name__ == '__main__':
+    trio.run(main)
diff --git a/tests/devx/test_debugger.py b/tests/devx/test_debugger.py
index 1b279dfd..cacab803 100644
--- a/tests/devx/test_debugger.py
+++ b/tests/devx/test_debugger.py
@@ -1,13 +1,13 @@
 """
 That "native" debug mode better work!
 
-All these tests can be understood (somewhat) by running the equivalent
-`examples/debugging/` scripts manually.
+All these tests can be understood (somewhat) by running the
+equivalent `examples/debugging/` scripts manually.
 
 TODO:
-    - none of these tests have been run successfully on windows yet but
-      there's been manual testing that verified it works.
-    - wonder if any of it'll work on OS X?
+  - none of these tests have been run successfully on windows yet but
+    there's been manual testing that verified it works.
+  - wonder if any of it'll work on OS X?
 
 """
 from __future__ import annotations
@@ -1156,6 +1156,54 @@ def test_ctxep_pauses_n_maybe_ipc_breaks(
             )
 
 
+def test_crash_handling_within_cancelled_root_actor(
+    spawn: PexpectSpawner,
+):
+    '''
+    Ensure that when only a root-actor is started via `open_root_actor()`
+    we can crash-handle in debug-mode despite self-cancellation.
+
+    More-or-less ensures we conditionally shield the pause in
+    `._root.open_root_actor()`'s `await debug._maybe_enter_pm()`
+    call.
+
+    '''
+    child = spawn('root_self_cancelled_w_error')
+    child.expect(PROMPT)
+
+    assert_before(
+        child,
+        [
+            "Actor.cancel_soon()` was called!",
+            "root cancelled",
+            _pause_msg,
+            "('root'",  # actor name
+        ]
+    )
+
+    child.sendline('c')
+    child.expect(PROMPT)
+    assert_before(
+        child,
+        [
+            _crash_msg,
+            "('root'",  # actor name
+            "AssertionError",
+            "assert 0",
+        ]
+    )
+
+    child.sendline('c')
+    child.expect(EOF)
+    assert_before(
+        child,
+        [
+            "AssertionError",
+            "assert 0",
+        ]
+    )
+
+
 # TODO: better error for "non-ideal" usage from the root actor.
 # -[ ] if called from an async scope emit a message that suggests
 #    using `await tractor.pause()` instead since it's less overhead