diff --git a/stdlib/@python2/__builtin__.pyi b/stdlib/@python2/__builtin__.pyi
index b7b68bbb7844..0b2c89e8d80c 100644
--- a/stdlib/@python2/__builtin__.pyi
+++ b/stdlib/@python2/__builtin__.pyi
@@ -863,9 +863,14 @@ def filter(__function: Callable[[_T], Any], __iterable: Iterable[_T]) -> List[_T
 def format(__value: object, __format_spec: str = ...) -> str: ...  # TODO unicode
 @overload
 def getattr(__o: Any, name: Text) -> Any: ...
+
+# While technically covered by the last overload, spelling out the types for None and bool
+# help mypy out in some tricky situations involving type context (aka bidirectional inference)
 @overload
 def getattr(__o: Any, name: Text, __default: None) -> Optional[Any]: ...
 @overload
+def getattr(__o: Any, name: Text, __default: bool) -> Union[Any, bool]: ...
+@overload
 def getattr(__o: Any, name: Text, __default: _T) -> Union[Any, _T]: ...
 def globals() -> Dict[str, Any]: ...
 def hasattr(__obj: Any, __name: Text) -> bool: ...
diff --git a/stdlib/@python2/builtins.pyi b/stdlib/@python2/builtins.pyi
index b7b68bbb7844..0b2c89e8d80c 100644
--- a/stdlib/@python2/builtins.pyi
+++ b/stdlib/@python2/builtins.pyi
@@ -863,9 +863,14 @@ def filter(__function: Callable[[_T], Any], __iterable: Iterable[_T]) -> List[_T
 def format(__value: object, __format_spec: str = ...) -> str: ...  # TODO unicode
 @overload
 def getattr(__o: Any, name: Text) -> Any: ...
+
+# While technically covered by the last overload, spelling out the types for None and bool
+# help mypy out in some tricky situations involving type context (aka bidirectional inference)
 @overload
 def getattr(__o: Any, name: Text, __default: None) -> Optional[Any]: ...
 @overload
+def getattr(__o: Any, name: Text, __default: bool) -> Union[Any, bool]: ...
+@overload
 def getattr(__o: Any, name: Text, __default: _T) -> Union[Any, _T]: ...
 def globals() -> Dict[str, Any]: ...
 def hasattr(__obj: Any, __name: Text) -> bool: ...
diff --git a/stdlib/builtins.pyi b/stdlib/builtins.pyi
index 865c6e9a12d7..8b45df95a266 100644
--- a/stdlib/builtins.pyi
+++ b/stdlib/builtins.pyi
@@ -1021,9 +1021,14 @@ class filter(Iterator[_T], Generic[_T]):
 def format(__value: object, __format_spec: str = ...) -> str: ...  # TODO unicode
 @overload
 def getattr(__o: Any, name: str) -> Any: ...
+
+# While technically covered by the last overload, spelling out the types for None and bool
+# help mypy out in some tricky situations involving type context (aka bidirectional inference)
 @overload
 def getattr(__o: Any, name: str, __default: None) -> Optional[Any]: ...
 @overload
+def getattr(__o: Any, name: str, __default: bool) -> Union[Any, bool]: ...
+@overload
 def getattr(__o: Any, name: str, __default: _T) -> Union[Any, _T]: ...
 def globals() -> Dict[str, Any]: ...
 def hasattr(__obj: Any, __name: str) -> bool: ...