diff --git a/src/attr/__init__.pyi b/src/attr/__init__.pyi
index 3cbe709e3..cdf9a9ff0 100644
--- a/src/attr/__init__.pyi
+++ b/src/attr/__init__.pyi
@@ -1,3 +1,5 @@
+import sys
+
 from typing import (
     Any,
     Callable,
@@ -60,13 +62,30 @@ NOTHING: object
 # NOTE: Factory lies about its return type to make this possible:
 # `x: List[int] # = Factory(list)`
 # Work around mypy issue #4554 in the common case by using an overload.
-@overload
-def Factory(factory: Callable[[], _T]) -> _T: ...
-@overload
-def Factory(
-    factory: Union[Callable[[Any], _T], Callable[[], _T]],
-    takes_self: bool = ...,
-) -> _T: ...
+if sys.version_info >= (3, 8):
+    from typing import Literal
+
+    @overload
+    def Factory(factory: Callable[[], _T]) -> _T: ...
+    @overload
+    def Factory(
+        factory: Callable[[Any], _T],
+        takes_self: Literal[True],
+    ) -> _T: ...
+    @overload
+    def Factory(
+        factory: Callable[[], _T],
+        takes_self: Literal[False],
+    ) -> _T: ...
+else:
+    @overload
+    def Factory(factory: Callable[[], _T]) -> _T: ...
+    @overload
+    def Factory(
+        factory: Union[Callable[[Any], _T], Callable[[], _T]],
+        takes_self: bool = ...,
+    ) -> _T: ...
+
 
 class Attribute(Generic[_T]):
     name: str
diff --git a/tests/typing_example.py b/tests/typing_example.py
index db05dec3b..13b5638db 100644
--- a/tests/typing_example.py
+++ b/tests/typing_example.py
@@ -250,3 +250,10 @@ class NGFrozen:
 @attr.s(collect_by_mro=True)
 class MRO:
     pass
+
+
+@attr.s
+class FactoryTest:
+    a: List[int] = attr.ib(default=attr.Factory(list))
+    b: List[Any] = attr.ib(default=attr.Factory(list, False))
+    c: List[int] = attr.ib(default=attr.Factory((lambda s: s.a), True))