diff --git a/third_party/2and3/click/core.pyi b/third_party/2and3/click/core.pyi
index 68308ffc3..ea3ef550a 100644
--- a/third_party/2and3/click/core.pyi
+++ b/third_party/2and3/click/core.pyi
@@ -356,7 +356,8 @@ class _ParamType:
 
 
 # This type is here to resolve https://github.com/python/mypy/issues/5275
-_ConvertibleType = Union[type, _ParamType, Tuple[type, ...], Callable[[str], Any], Callable[[Optional[str]], Any]]
+_ConvertibleType = Union[type, _ParamType, Tuple[Union[type, _ParamType], ...],
+                         Callable[[str], Any], Callable[[Optional[str]], Any]]
 
 
 class Parameter:
diff --git a/third_party/2and3/click/testing.pyi b/third_party/2and3/click/testing.pyi
index 6b16df9b2..bffe29eb8 100644
--- a/third_party/2and3/click/testing.pyi
+++ b/third_party/2and3/click/testing.pyi
@@ -56,7 +56,7 @@ class CliRunner:
     def make_env(self, overrides: Optional[Mapping[str, str]] = ...) -> Dict[str, str]: ...
     def isolation(
         self,
-        input: Optional[IO] = ...,
+        input: Optional[Union[bytes, Text, IO]] = ...,
         env: Optional[Mapping[str, str]] = ...,
         color: bool = ...,
     ) -> ContextManager[BinaryIO]: ...
@@ -64,7 +64,7 @@ class CliRunner:
         self,
         cli: BaseCommand,
         args: Optional[Union[str, Iterable[str]]] = ...,
-        input: Optional[IO] = ...,
+        input: Optional[Union[bytes, Text, IO]] = ...,
         env: Optional[Mapping[str, str]] = ...,
         catch_exceptions: bool = ...,
         color: bool = ...,
diff --git a/third_party/2and3/flask/testing.pyi b/third_party/2and3/flask/testing.pyi
index 4c562e580..79459287c 100644
--- a/third_party/2and3/flask/testing.pyi
+++ b/third_party/2and3/flask/testing.pyi
@@ -4,7 +4,7 @@
 
 from click import BaseCommand
 from click.testing import CliRunner, Result
-from typing import Any, IO, Iterable, Mapping, Optional, Union, TypeVar
+from typing import Any, IO, Iterable, Mapping, Optional, Text, TypeVar, Union
 from werkzeug.test import Client
 
 def make_test_environ_builder(app: Any, path: str = ..., base_url: Optional[Any] = ..., subdomain: Optional[Any] = ..., url_scheme: Optional[Any] = ..., *args: Any, **kwargs: Any): ...
@@ -29,7 +29,7 @@ class FlaskCliRunner(CliRunner):
         self,
         cli: Optional[BaseCommand] = ...,
         args: Optional[Union[str, Iterable[str]]] = ...,
-        input: Optional[IO] = ...,
+        input: Optional[Union[bytes, IO, Text]] = ...,
         env: Optional[Mapping[str, str]] = ...,
         catch_exceptions: bool = ...,
         color: bool = ...,