diff --git a/stdlib/ftplib.pyi b/stdlib/ftplib.pyi
index f24d14fbf..2d2ffa9af 100644
--- a/stdlib/ftplib.pyi
+++ b/stdlib/ftplib.pyi
@@ -87,7 +87,7 @@ class FTP:
     def makepasv(self) -> tuple[str, int]: ...
     def login(self, user: str = "", passwd: str = "", acct: str = "") -> str: ...
     # In practice, `rest` rest can actually be anything whose str() is an integer sequence, so to make it simple we allow integers.
-    def ntransfercmd(self, cmd: str, rest: int | str | None = None) -> tuple[socket, int]: ...
+    def ntransfercmd(self, cmd: str, rest: int | str | None = None) -> tuple[socket, int | None]: ...
     def transfercmd(self, cmd: str, rest: int | str | None = None) -> socket: ...
     def retrbinary(
         self, cmd: str, callback: Callable[[bytes], object], blocksize: int = 8192, rest: int | str | None = None
diff --git a/stdlib/urllib/request.pyi b/stdlib/urllib/request.pyi
index 8f99c5837..079c97555 100644
--- a/stdlib/urllib/request.pyi
+++ b/stdlib/urllib/request.pyi
@@ -173,7 +173,7 @@ class HTTPPasswordMgr:
     def add_password(self, realm: str, uri: str | Sequence[str], user: str, passwd: str) -> None: ...
     def find_user_password(self, realm: str, authuri: str) -> tuple[str | None, str | None]: ...
     def is_suburi(self, base: str, test: str) -> bool: ...  # undocumented
-    def reduce_uri(self, uri: str, default_port: bool = True) -> str: ...  # undocumented
+    def reduce_uri(self, uri: str, default_port: bool = True) -> tuple[str, str]: ...  # undocumented
 
 class HTTPPasswordMgrWithDefaultRealm(HTTPPasswordMgr):
     def add_password(self, realm: str | None, uri: str | Sequence[str], user: str, passwd: str) -> None: ...
@@ -184,7 +184,7 @@ class HTTPPasswordMgrWithPriorAuth(HTTPPasswordMgrWithDefaultRealm):
         self, realm: str | None, uri: str | Sequence[str], user: str, passwd: str, is_authenticated: bool = False
     ) -> None: ...
     def update_authenticated(self, uri: str | Sequence[str], is_authenticated: bool = False) -> None: ...
-    def is_authenticated(self, authuri: str) -> bool: ...
+    def is_authenticated(self, authuri: str) -> bool | None: ...
 
 class AbstractBasicAuthHandler:
     rx: ClassVar[Pattern[str]]  # undocumented
@@ -212,7 +212,7 @@ class AbstractDigestAuthHandler:
     def http_error_auth_reqed(self, auth_header: str, host: str, req: Request, headers: HTTPMessage) -> None: ...
     def retry_http_digest_auth(self, req: Request, auth: str) -> _UrlopenRet | None: ...
     def get_cnonce(self, nonce: str) -> str: ...
-    def get_authorization(self, req: Request, chal: Mapping[str, str]) -> str: ...
+    def get_authorization(self, req: Request, chal: Mapping[str, str]) -> str | None: ...
     def get_algorithm_impls(self, algorithm: str) -> tuple[Callable[[str], str], Callable[[str, str], str]]: ...
     def get_entity_digest(self, data: ReadableBuffer | None, chal: Mapping[str, str]) -> str | None: ...
 
@@ -269,7 +269,7 @@ class ftpwrapper:  # undocumented
     def file_close(self) -> None: ...
     def init(self) -> None: ...
     def real_close(self) -> None: ...
-    def retrfile(self, file: str, type: str) -> tuple[addclosehook, int]: ...
+    def retrfile(self, file: str, type: str) -> tuple[addclosehook, int | None]: ...
 
 class FTPHandler(BaseHandler):
     def ftp_open(self, req: Request) -> addinfourl: ...