diff --git a/CHANGES.rst b/CHANGES.rst
index c7ae2f651f..9f79995b46 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -4,6 +4,7 @@ Version 3.0.1
 Unreleased
 
 -   Correct type for ``path`` argument to ``send_file``. :issue:`5230`
+-   Fix a typo in an error message for the ``flask run --key`` option. :pr:`5344`
 
 
 Version 3.0.0
diff --git a/docs/server.rst b/docs/server.rst
index d38aa12089..11e976bc73 100644
--- a/docs/server.rst
+++ b/docs/server.rst
@@ -76,8 +76,8 @@ following example shows that process id 6847 is using port 5000.
             TCP 127.0.0.1:5000 0.0.0.0:0 LISTENING 6847
 
 macOS Monterey and later automatically starts a service that uses port
-5000. To disable the service, go to System Preferences, Sharing, and
-disable "AirPlay Receiver".
+5000. You can choose to disable this service instead of using a different port by
+searching for "AirPlay Receiver" in System Preferences and toggling it off.
 
 
 Deferred Errors on Reload
diff --git a/pyproject.toml b/pyproject.toml
index ca0eda791a..9031e0596a 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -79,7 +79,7 @@ source = ["src", "*/site-packages"]
 
 [tool.mypy]
 python_version = "3.8"
-files = ["src/flask"]
+files = ["src/flask", "tests/typing"]
 show_error_codes = true
 pretty = true
 #strict = true
diff --git a/requirements/dev.txt b/requirements/dev.txt
index 49c08c9b14..5ce2a7cf33 100644
--- a/requirements/dev.txt
+++ b/requirements/dev.txt
@@ -28,7 +28,7 @@ click==8.1.7
     # via pip-tools
 colorama==0.4.6
     # via tox
-cryptography==41.0.5
+cryptography==41.0.7
     # via -r typing.in
 distlib==0.3.7
     # via virtualenv
@@ -52,7 +52,7 @@ jinja2==3.1.2
     # via sphinx
 markupsafe==2.1.3
     # via jinja2
-mypy==1.6.1
+mypy==1.7.1
     # via -r typing.in
 mypy-extensions==1.0.0
     # via mypy
@@ -130,7 +130,7 @@ sphinxcontrib-qthelp==1.0.6
     # via sphinx
 sphinxcontrib-serializinghtml==1.1.9
     # via sphinx
-tox==4.11.3
+tox==4.11.4
     # via -r dev.in
 types-contextvars==2.4.7.3
     # via -r typing.in
diff --git a/requirements/typing.txt b/requirements/typing.txt
index 990ff6bb79..212ba0e65f 100644
--- a/requirements/typing.txt
+++ b/requirements/typing.txt
@@ -6,9 +6,9 @@
 #
 cffi==1.16.0
     # via cryptography
-cryptography==41.0.5
+cryptography==41.0.7
     # via -r typing.in
-mypy==1.6.1
+mypy==1.7.1
     # via -r typing.in
 mypy-extensions==1.0.0
     # via mypy
diff --git a/src/flask/cli.py b/src/flask/cli.py
index dda266b30c..751dfd1f60 100644
--- a/src/flask/cli.py
+++ b/src/flask/cli.py
@@ -795,7 +795,9 @@ def _validate_key(ctx, param, value):
 
         if is_context:
             raise click.BadParameter(
-                'When "--cert" is an SSLContext object, "--key is not used.', ctx, param
+                'When "--cert" is an SSLContext object, "--key" is not used.',
+                ctx,
+                param,
             )
 
         if not cert:
diff --git a/src/flask/helpers.py b/src/flask/helpers.py
index 8460891215..b4ca16bf12 100644
--- a/src/flask/helpers.py
+++ b/src/flask/helpers.py
@@ -171,7 +171,7 @@ def index():
         return current_app.response_class()
     if len(args) == 1:
         args = args[0]
-    return current_app.make_response(args)  # type: ignore
+    return current_app.make_response(args)
 
 
 def url_for(