diff --git a/trio/_tests/test_threads.py b/trio/_tests/test_threads.py
index 84409ae83c..4595b5867a 100644
--- a/trio/_tests/test_threads.py
+++ b/trio/_tests/test_threads.py
@@ -13,9 +13,17 @@
 import pytest
 import sniffio
 
-from .. import CapacityLimiter, Event, _core, fail_after, sleep, sleep_forever
+from .. import (
+    CapacityLimiter,
+    Event,
+    _core,
+    fail_after,
+    move_on_after,
+    sleep,
+    sleep_forever,
+)
 from .._core._tests.test_ki import ki_self
-from .._core._tests.tutil import buggy_pypy_asyncgens
+from .._core._tests.tutil import buggy_pypy_asyncgens, slow
 from .._threads import (
     current_default_thread_limiter,
     from_thread_check_cancelled,
@@ -1015,3 +1023,19 @@ async def test_from_thread_check_cancelled_raises_in_foreign_threads():
     _core.start_thread_soon(from_thread_check_cancelled, lambda _: q.put(_))
     with pytest.raises(RuntimeError):
         q.get(timeout=1).unwrap()
+
+
+@slow
+async def test_reentry_doesnt_deadlock():
+    # Regression test for issue noticed in GH-2827
+    # The failure mode is to hang the whole test suite, unfortunately.
+    # XXX consider running this in a subprocess with a timeout, if it comes up again!
+
+    async def child() -> None:
+        while True:
+            await to_thread_run_sync(from_thread_run, sleep, 0, cancellable=False)
+
+    with move_on_after(2):
+        async with _core.open_nursery() as nursery:
+            for _ in range(4):
+                nursery.start_soon(child)
diff --git a/trio/_threads.py b/trio/_threads.py
index d44e4b68f8..023b1c198e 100644
--- a/trio/_threads.py
+++ b/trio/_threads.py
@@ -93,13 +93,11 @@ async def run(self) -> None:
         task = trio.lowlevel.current_task()
         old_context = task.context
         task.context = self.context.copy()
-        try:
-            await trio.lowlevel.cancel_shielded_checkpoint()
-            result = await outcome.acapture(self.unprotected_afn)
-            self.queue.put_nowait(result)
-        finally:
-            task.context = old_context
-            await trio.lowlevel.cancel_shielded_checkpoint()
+        await trio.lowlevel.cancel_shielded_checkpoint()
+        result = await outcome.acapture(self.unprotected_afn)
+        task.context = old_context
+        await trio.lowlevel.cancel_shielded_checkpoint()
+        self.queue.put_nowait(result)
 
     async def run_system(self) -> None:
         result = await outcome.acapture(self.unprotected_afn)