2 files changed, 69 insertions, 0 deletions
diff --git a/Lib/test/test_contextlib.py b/Lib/test/test_contextlib.py
index 43b8507..7982d9d 100644
--- a/Lib/test/test_contextlib.py
+++ b/Lib/test/test_contextlib.py
@@ -799,6 +799,40 @@ class TestBaseExitStack:
         self.assertIsInstance(inner_exc, ValueError)
         self.assertIsInstance(inner_exc.__context__, ZeroDivisionError)
 
+    def test_exit_exception_explicit_none_context(self):
+        # Ensure ExitStack chaining matches actual nested `with` statements
+        # regarding explicit __context__ = None.
+
+        class MyException(Exception):
+            pass
+
+        @contextmanager
+        def my_cm():
+            try:
+                yield
+            except BaseException:
+                exc = MyException()
+                try:
+                    raise exc
+                finally:
+                    exc.__context__ = None
+
+        @contextmanager
+        def my_cm_with_exit_stack():
+            with self.exit_stack() as stack:
+                stack.enter_context(my_cm())
+                yield stack
+
+        for cm in (my_cm, my_cm_with_exit_stack):
+            with self.subTest():
+                try:
+                    with cm():
+                        raise IndexError()
+                except MyException as exc:
+                    self.assertIsNone(exc.__context__)
+                else:
+                    self.fail("Expected IndexError, but no exception was raised")
+
     def test_exit_exception_non_suppressing(self):
         # http://bugs.python.org/issue19092
         def raise_exc(exc):
diff --git a/Lib/test/test_contextlib_async.py b/Lib/test/test_contextlib_async.py
index c738bf3..c16c7ec 100644
--- a/Lib/test/test_contextlib_async.py
+++ b/Lib/test/test_contextlib_async.py
@@ -647,6 +647,41 @@ class TestAsyncExitStack(TestBaseExitStack, unittest.TestCase):
         self.assertIsInstance(inner_exc.__context__, ZeroDivisionError)
 
     @_async_test
+    async def test_async_exit_exception_explicit_none_context(self):
+        # Ensure AsyncExitStack chaining matches actual nested `with` statements
+        # regarding explicit __context__ = None.
+
+        class MyException(Exception):
+            pass
+
+        @asynccontextmanager
+        async def my_cm():
+            try:
+                yield
+            except BaseException:
+                exc = MyException()
+                try:
+                    raise exc
+                finally:
+                    exc.__context__ = None
+
+        @asynccontextmanager
+        async def my_cm_with_exit_stack():
+            async with self.exit_stack() as stack:
+                await stack.enter_async_context(my_cm())
+                yield stack
+
+        for cm in (my_cm, my_cm_with_exit_stack):
+            with self.subTest():
+                try:
+                    async with cm():
+                        raise IndexError()
+                except MyException as exc:
+                    self.assertIsNone(exc.__context__)
+                else:
+                    self.fail("Expected IndexError, but no exception was raised")
+
+    @_async_test
     async def test_instance_bypass_async(self):
         class Example(object): pass
         cm = Example()