diff --git a/scripts/datamodel_generate_client.py b/scripts/datamodel_generate_client.py
index 1ce959a..c207133 100755
--- a/scripts/datamodel_generate_client.py
+++ b/scripts/datamodel_generate_client.py
@@ -800,7 +800,7 @@ def request_sync(self, *, type_: Any, **kwargs: Any) -> Any:
         """
         return get_event_loop().run_until_complete(self.request(type_=type_, **kwargs))
 
-    async def send(self, request: Request, type_: Type[T]) -> T | str:
+    async def send(self, request: Request, type_: Type[T]) -> T | str | None:
         response = await self.middleware(request, self.send_inner)
         if response.status_code in [200, 201, 204]:
             try:
diff --git a/th_cli/api_lib_autogen/api_client.py b/th_cli/api_lib_autogen/api_client.py
index 4d7d04c..f5b905a 100644
--- a/th_cli/api_lib_autogen/api_client.py
+++ b/th_cli/api_lib_autogen/api_client.py
@@ -108,7 +108,7 @@ def request_sync(self, *, type_: Any, **kwargs: Any) -> Any:
         """
         return get_event_loop().run_until_complete(self.request(type_=type_, **kwargs))
 
-    async def send(self, request: Request, type_: Type[T]) -> T | str:
+    async def send(self, request: Request, type_: Type[T]) -> T | str | None:
         response = await self.middleware(request, self.send_inner)
         if response.status_code in [200, 201, 204]:
             try: