diff --git a/test-data/unit/check-based-contextmanager.test b/test-data/unit/check-based-contextmanager.test
new file mode 100644
index 000000000..a9a76d97d
--- /dev/null
+++ b/test-data/unit/check-based-contextmanager.test
@@ -0,0 +1,30 @@
+[case testContextManagerWorkProperly]
+from __future__ import annotations
+
+class Base:
+    def __enter__(self): ...
+class Swallow(Base):
+    def __exit__(self, x: object, y: object, z: object) -> True: return True
+class Pass(Base):
+    def __exit__(self, x: object, y: object, z: object) -> False | None: return None
+class Normal(Base):
+    def __exit__(self, x: object, y: object, z: object) -> bool | None: return True
+
+def f1():
+    with Swallow():  # E: Call to untyped function "Swallow" in typed context  [no-untyped-call]
+        raise Exception
+    1
+
+def f2():
+    with Pass(): # E: Call to untyped function "Pass" in typed context  [no-untyped-call]
+        raise Exception
+    1  # E: Statement is unreachable  [unreachable]
+
+def f3():
+    with Normal(): # E: Call to untyped function "Normal" in typed context  [no-untyped-call]
+        raise Exception
+    1
+    with Normal(): # E: Call to untyped function "Normal" in typed context  [no-untyped-call]
+        return
+    1  # E: Statement is unreachable  [unreachable]
+[builtins fixtures/exception.pyi]
diff --git a/test.py b/test.py
new file mode 100644
index 000000000..b7c2f8275
--- /dev/null
+++ b/test.py
@@ -0,0 +1,30 @@
+from __future__ import annotations
+
+
+class Base:
+    def __enter__(self): ...
+class Swallow(Base):
+    def __exit__(self, x: object, y: object, z: object) -> True: return True
+class Pass(Base):
+    def __exit__(self, x: object, y: object, z: object) -> False | None: return None
+class Normal(Base):
+    def __exit__(self, x: object, y: object, z: object) -> bool: return True
+
+# def f1():
+#     with Swallow():
+#         raise Exception
+#     1
+
+# def f2():
+#     with Pass():
+#         raise Exception
+#     1  # E: Statement is unreachable  [unreachable]
+
+def f3():
+    with Normal():
+        raise Exception
+    1
+    with Normal():
+        return
+    1  # E: Statement is unreachable  [unreachable]
+liam is a nigger