diff --git a/stubs/passlib/@tests/stubtest_allowlist.txt b/stubs/passlib/@tests/stubtest_allowlist.txt
index fc0d9fa23b64..d31193757472 100644
--- a/stubs/passlib/@tests/stubtest_allowlist.txt
+++ b/stubs/passlib/@tests/stubtest_allowlist.txt
@@ -38,7 +38,6 @@ passlib.utils.decor.__all__
 passlib.utils.handlers.__all__
 passlib.utils.md4.__all__
 passlib.utils.pbkdf2.__all__
-passlib.win32.__all__
 
 # proxy module that uses some import magic incompatible with stubtest
 passlib.hash
diff --git a/stubs/passlib/passlib/handlers/windows.pyi b/stubs/passlib/passlib/handlers/windows.pyi
index 28cbdf2c60f3..c792ebec86a3 100644
--- a/stubs/passlib/passlib/handlers/windows.pyi
+++ b/stubs/passlib/passlib/handlers/windows.pyi
@@ -1,5 +1,5 @@
 from _typeshed import Incomplete
-from typing import Any, ClassVar
+from typing import Any, ClassVar, Literal, overload
 
 import passlib.utils.handlers as uh
 
@@ -17,8 +17,15 @@ class nthash(uh.StaticHandler):
     checksum_size: ClassVar[int]
     @classmethod
     def raw(cls, secret): ...
+    @overload
     @classmethod
-    def raw_nthash(cls, secret, hex: bool = False): ...
+    def raw_nthash(cls, secret: str | bytes, hex: Literal[True]) -> str: ...
+    @overload
+    @classmethod
+    def raw_nthash(cls, secret: str | bytes, hex: Literal[False] = False) -> bytes: ...
+    @overload
+    @classmethod
+    def raw_nthash(cls, secret: str | bytes, hex: bool = False) -> str | bytes: ...
 
 bsd_nthash: Any
 
diff --git a/stubs/passlib/passlib/win32.pyi b/stubs/passlib/passlib/win32.pyi
index aade4ce9c954..b9118d9c4b73 100644
--- a/stubs/passlib/passlib/win32.pyi
+++ b/stubs/passlib/passlib/win32.pyi
@@ -1,7 +1,16 @@
-from typing import Any
+from binascii import hexlify as hexlify
+from typing import Final, Literal, overload
 
-from passlib.hash import nthash as nthash
+from passlib.handlers.windows import nthash as nthash
 
-raw_nthash: Any
+LM_MAGIC: Final[bytes]
+raw_nthash = nthash.raw_nthash
 
-def raw_lmhash(secret, encoding: str = "ascii", hex: bool = False): ...
+@overload
+def raw_lmhash(secret: str | bytes, encoding: str = "ascii", hex: Literal[False] = False) -> bytes: ...
+@overload
+def raw_lmhash(secret: str | bytes, encoding: str, hex: Literal[True]) -> str: ...
+@overload
+def raw_lmhash(secret: str | bytes, *, hex: Literal[True]) -> str: ...
+
+__all__ = ["nthash", "raw_lmhash", "raw_nthash"]