diff --git a/third_party/2and3/requests/adapters.pyi b/third_party/2and3/requests/adapters.pyi
index 190056755..bcfb8acd7 100644
--- a/third_party/2and3/requests/adapters.pyi
+++ b/third_party/2and3/requests/adapters.pyi
@@ -47,7 +47,7 @@ class BaseAdapter:
     def send(self,
              request: PreparedRequest,
              stream: bool = ...,
-             timeout: Union[None, float, Tuple[float, float]] = ...,
+             timeout: Union[None, float, Tuple[float, float], Tuple[float, None]] = ...,
              verify: Union[bool, str] = ...,
              cert: Union[None, Union[bytes, Text], Container[Union[bytes, Text]]] = ...,
              proxies: Optional[Mapping[str, str]] = ...) -> Response: ...
@@ -73,7 +73,7 @@ class HTTPAdapter(BaseAdapter):
     def send(self,
              request: PreparedRequest,
              stream: bool = ...,
-             timeout: Union[None, float, Tuple[float, float]] = ...,
+             timeout: Union[None, float, Tuple[float, float], Tuple[float, None]] = ...,
              verify: Union[bool, str] = ...,
              cert: Union[None, Union[bytes, Text], Container[Union[bytes, Text]]] = ...,
              proxies: Optional[Mapping[str, str]] = ...) -> Response: ...
diff --git a/third_party/2and3/requests/sessions.pyi b/third_party/2and3/requests/sessions.pyi
index f09dbec2e..dc0b63800 100644
--- a/third_party/2and3/requests/sessions.pyi
+++ b/third_party/2and3/requests/sessions.pyi
@@ -86,7 +86,7 @@ class Session(SessionRedirectMixin):
                 cookies: Union[None, RequestsCookieJar, MutableMapping[Text, Text]] = ...,
                 files: Optional[MutableMapping[Text, IO[Any]]] = ...,
                 auth: Union[None, Tuple[Text, Text], _auth.AuthBase, Callable[[Request], Request]] = ...,
-                timeout: Union[None, float, Tuple[float, float]] = ...,
+                timeout: Union[None, float, Tuple[float, float], Tuple[float, None]] = ...,
                 allow_redirects: Optional[bool] = ...,
                 proxies: Optional[MutableMapping[Text, Text]] = ...,
                 hooks: Optional[_HooksInput] = ...,