diff --git a/pyrightconfig.stricter.json b/pyrightconfig.stricter.json
index be0163441020..7a2fda7dab78 100644
--- a/pyrightconfig.stricter.json
+++ b/pyrightconfig.stricter.json
@@ -38,6 +38,7 @@
         "stubs/caldav",
         "stubs/cffi",
         "stubs/click-default-group",
+        "stubs/click-web",
         "stubs/commonmark",
         "stubs/corus",
         "stubs/dateparser",
diff --git a/stubs/click-web/METADATA.toml b/stubs/click-web/METADATA.toml
new file mode 100644
index 000000000000..8153c7eece59
--- /dev/null
+++ b/stubs/click-web/METADATA.toml
@@ -0,0 +1,2 @@
+version = "0.8.*"
+upstream_repository = "https://github.com/fredrik-corneliusson/click-web"
diff --git a/stubs/click-web/click_web/__init__.pyi b/stubs/click-web/click_web/__init__.pyi
new file mode 100644
index 000000000000..9e43b4a356e6
--- /dev/null
+++ b/stubs/click-web/click_web/__init__.pyi
@@ -0,0 +1,9 @@
+import types
+
+import click
+import flask
+import jinja2
+
+jinja_env: jinja2.Environment
+
+def create_click_web_app(module: types.ModuleType, command: click.BaseCommand, root: str = "/") -> flask.Flask: ...
diff --git a/stubs/click-web/click_web/exceptions.pyi b/stubs/click-web/click_web/exceptions.pyi
new file mode 100644
index 000000000000..172a2026a871
--- /dev/null
+++ b/stubs/click-web/click_web/exceptions.pyi
@@ -0,0 +1,2 @@
+class ClickWebException(Exception): ...
+class CommandNotFound(ClickWebException): ...
diff --git a/stubs/click-web/click_web/web_click_types.pyi b/stubs/click-web/click_web/web_click_types.pyi
new file mode 100644
index 000000000000..3cfe56e58a91
--- /dev/null
+++ b/stubs/click-web/click_web/web_click_types.pyi
@@ -0,0 +1,14 @@
+import click
+
+class EmailParamType(click.ParamType):
+    def convert(self, value: str, param: click.Parameter, ctx: click.Context) -> str: ...
+
+class PasswordParamType(click.ParamType):
+    def convert(self, value: str, param: click.Parameter, ctx: click.Context) -> str: ...
+
+class TextAreaParamType(click.ParamType):
+    def convert(self, value: str, param: click.Parameter, ctx: click.Context) -> str: ...
+
+EMAIL_TYPE: EmailParamType
+PASSWORD_TYPE: PasswordParamType
+TEXTAREA_TYPE: TextAreaParamType