diff --git a/end_to_end_tests/golden-record/my_test_api_client/types.py b/end_to_end_tests/golden-record/my_test_api_client/types.py
index 230efea92..599eeb9f5 100644
--- a/end_to_end_tests/golden-record/my_test_api_client/types.py
+++ b/end_to_end_tests/golden-record/my_test_api_client/types.py
@@ -1,12 +1,12 @@
 """ Contains some shared types for properties """
 from http import HTTPStatus
-from typing import BinaryIO, Generic, MutableMapping, Optional, Tuple, TypeVar
+from typing import BinaryIO, Generic, Literal, MutableMapping, Optional, Tuple, TypeVar
 
 import attr
 
 
 class Unset:
-    def __bool__(self) -> bool:
+    def __bool__(self) -> Literal[False]:
         return False
 
 
diff --git a/integration-tests/integration_tests/types.py b/integration-tests/integration_tests/types.py
index 230efea92..599eeb9f5 100644
--- a/integration-tests/integration_tests/types.py
+++ b/integration-tests/integration_tests/types.py
@@ -1,12 +1,12 @@
 """ Contains some shared types for properties """
 from http import HTTPStatus
-from typing import BinaryIO, Generic, MutableMapping, Optional, Tuple, TypeVar
+from typing import BinaryIO, Generic, Literal, MutableMapping, Optional, Tuple, TypeVar
 
 import attr
 
 
 class Unset:
-    def __bool__(self) -> bool:
+    def __bool__(self) -> Literal[False]:
         return False
 
 
diff --git a/openapi_python_client/templates/types.py.jinja b/openapi_python_client/templates/types.py.jinja
index c746db6e1..cfb990d85 100644
--- a/openapi_python_client/templates/types.py.jinja
+++ b/openapi_python_client/templates/types.py.jinja
@@ -1,12 +1,12 @@
 """ Contains some shared types for properties """
 from http import HTTPStatus
-from typing import Any, BinaryIO, Generic, MutableMapping, Optional, Tuple, TypeVar
+from typing import Any, BinaryIO, Generic, MutableMapping, Optional, Tuple, TypeVar, Literal
 
 import attr
 
 
 class Unset:
-    def __bool__(self) -> bool:
+    def __bool__(self) -> Literal[False]:
         return False