diff --git a/stdlib/_typeshed/__init__.pyi b/stdlib/_typeshed/__init__.pyi
index 7201819b25ed..fa6678289347 100644
--- a/stdlib/_typeshed/__init__.pyi
+++ b/stdlib/_typeshed/__init__.pyi
@@ -82,19 +82,22 @@ class SupportsNext(Protocol[_T_co]):
 class SupportsAnext(Protocol[_T_co]):
     def __anext__(self) -> Awaitable[_T_co]: ...
 
+class SupportsBool(Protocol):
+    def __bool__(self) -> bool: ...
+
 # Comparison protocols
 
 class SupportsDunderLT(Protocol[_T_contra]):
-    def __lt__(self, other: _T_contra, /) -> bool: ...
+    def __lt__(self, other: _T_contra, /) -> SupportsBool: ...
 
 class SupportsDunderGT(Protocol[_T_contra]):
-    def __gt__(self, other: _T_contra, /) -> bool: ...
+    def __gt__(self, other: _T_contra, /) -> SupportsBool: ...
 
 class SupportsDunderLE(Protocol[_T_contra]):
-    def __le__(self, other: _T_contra, /) -> bool: ...
+    def __le__(self, other: _T_contra, /) -> SupportsBool: ...
 
 class SupportsDunderGE(Protocol[_T_contra]):
-    def __ge__(self, other: _T_contra, /) -> bool: ...
+    def __ge__(self, other: _T_contra, /) -> SupportsBool: ...
 
 class SupportsAllComparisons(
     SupportsDunderLT[Any], SupportsDunderGT[Any], SupportsDunderLE[Any], SupportsDunderGE[Any], Protocol
diff --git a/stdlib/builtins.pyi b/stdlib/builtins.pyi
index 2fea1b29a434..6d0b0ef612cc 100644
--- a/stdlib/builtins.pyi
+++ b/stdlib/builtins.pyi
@@ -19,6 +19,7 @@ from _typeshed import (
     SupportsAdd,
     SupportsAiter,
     SupportsAnext,
+    SupportsBool,
     SupportsDivMod,
     SupportsFlush,
     SupportsIter,
@@ -908,7 +909,12 @@ class memoryview(Sequence[_I]):
 
 @final
 class bool(int):
-    def __new__(cls, o: object = ..., /) -> Self: ...
+    @overload
+    def __new__(cls) -> Literal[False]: ...
+    @overload
+    def __new__(cls, o: SupportsBool | Sized, /) -> bool: ...
+    @overload
+    def __new__(cls, o: object, /) -> Literal[True]: ...
     # The following overloads could be represented more elegantly with a TypeVar("_B", bool, int),
     # however mypy has a bug regarding TypeVar constraints (https://github.com/python/mypy/issues/11880).
     @overload