diff --git a/CHANGES.rst b/CHANGES.rst
index 0dea8e3a..42d91ea3 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -33,6 +33,9 @@ Unreleased
 -   Add ``--env-file`` option to the ``flask`` CLI. This allows
     specifying a dotenv file to load in addition to ``.env`` and
     ``.flaskenv``. :issue:`3108`
+-   It is no longer required to decorate custom CLI commands on
+    ``app.cli`` or ``blueprint.cli`` with ``@with_appcontext``, an app
+    context will already be active at that point. :issue:`2410`
 
 
 Version 2.1.3
diff --git a/docs/cli.rst b/docs/cli.rst
index 7bab8fac..b5724d49 100644
--- a/docs/cli.rst
+++ b/docs/cli.rst
@@ -437,12 +437,14 @@ commands directly to the application's level:
 Application Context
 ~~~~~~~~~~~~~~~~~~~
 
-Commands added using the Flask app's :attr:`~Flask.cli`
-:meth:`~cli.AppGroup.command` decorator will be executed with an application
-context pushed, so your command and extensions have access to the app and its
-configuration. If you create a command using the Click :func:`~click.command`
-decorator instead of the Flask decorator, you can use
-:func:`~cli.with_appcontext` to get the same behavior. ::
+Commands added using the Flask app's :attr:`~Flask.cli` or
+:class:`~flask.cli.FlaskGroup` :meth:`~cli.AppGroup.command` decorator
+will be executed with an application context pushed, so your custom
+commands and parameters have access to the app and its configuration. The
+:func:`~cli.with_appcontext` decorator can be used to get the same
+behavior, but is not needed in most cases.
+
+.. code-block:: python
 
     import click
     from flask.cli import with_appcontext
@@ -454,12 +456,6 @@ decorator instead of the Flask decorator, you can use
 
     app.cli.add_command(do_work)
 
-If you're sure a command doesn't need the context, you can disable it::
-
-    @app.cli.command(with_appcontext=False)
-    def do_work():
-        ...
-
 
 Plugins
 -------
diff --git a/docs/tutorial/database.rst b/docs/tutorial/database.rst
index b2852197..934f6008 100644
--- a/docs/tutorial/database.rst
+++ b/docs/tutorial/database.rst
@@ -40,7 +40,6 @@ response is sent.
 
     import click
     from flask import current_app, g
-    from flask.cli import with_appcontext
 
 
     def get_db():
@@ -128,7 +127,6 @@ Add the Python functions that will run these SQL commands to the
 
 
     @click.command('init-db')
-    @with_appcontext
     def init_db_command():
         """Clear the existing data and create new tables."""
         init_db()
diff --git a/examples/tutorial/flaskr/db.py b/examples/tutorial/flaskr/db.py
index f1e2dc30..acaa4ae3 100644
--- a/examples/tutorial/flaskr/db.py
+++ b/examples/tutorial/flaskr/db.py
@@ -3,7 +3,6 @@ import sqlite3
 import click
 from flask import current_app
 from flask import g
-from flask.cli import with_appcontext
 
 
 def get_db():
@@ -39,7 +38,6 @@ def init_db():
 
 
 @click.command("init-db")
-@with_appcontext
 def init_db_command():
     """Clear existing data and create new tables."""
     init_db()
diff --git a/src/flask/cli.py b/src/flask/cli.py
index 40f1de54..321794b6 100644
--- a/src/flask/cli.py
+++ b/src/flask/cli.py
@@ -410,15 +410,25 @@ pass_script_info = click.make_pass_decorator(ScriptInfo, ensure=True)
 
 def with_appcontext(f):
     """Wraps a callback so that it's guaranteed to be executed with the
-    script's application context.  If callbacks are registered directly
-    to the ``app.cli`` object then they are wrapped with this function
-    by default unless it's disabled.
+    script's application context.
+
+    Custom commands (and their options) registered under ``app.cli`` or
+    ``blueprint.cli`` will always have an app context available, this
+    decorator is not required in that case.
+
+    .. versionchanged:: 2.2
+        The app context is active for subcommands as well as the
+        decorated callback. The app context is always available to
+        ``app.cli`` command and parameter callbacks.
     """
 
     @click.pass_context
     def decorator(__ctx, *args, **kwargs):
-        with __ctx.ensure_object(ScriptInfo).load_app().app_context():
-            return __ctx.invoke(f, *args, **kwargs)
+        if not current_app:
+            app = __ctx.ensure_object(ScriptInfo).load_app()
+            __ctx.with_resource(app.app_context())
+
+        return __ctx.invoke(f, *args, **kwargs)
 
     return update_wrapper(decorator, f)
 
@@ -587,6 +597,10 @@ class FlaskGroup(AppGroup):
         Added the ``-A/--app``, ``-E/--env``, ``--debug/--no-debug``,
         and ``-e/--env-file`` options.
 
+    .. versionchanged:: 2.2
+        An app context is pushed when running ``app.cli`` commands, so
+        ``@with_appcontext`` is no longer required for those commands.
+
     .. versionchanged:: 1.0
         If installed, python-dotenv will be used to load environment variables
         from :file:`.env` and :file:`.flaskenv` files.
@@ -660,9 +674,18 @@ class FlaskGroup(AppGroup):
         # Look up commands provided by the app, showing an error and
         # continuing if the app couldn't be loaded.
         try:
-            return info.load_app().cli.get_command(ctx, name)
+            app = info.load_app()
         except NoAppException as e:
             click.secho(f"Error: {e.format_message()}\n", err=True, fg="red")
+            return None
+
+        # Push an app context for the loaded app unless it is already
+        # active somehow. This makes the context available to parameter
+        # and command callbacks without needing @with_appcontext.
+        if not current_app or current_app._get_current_object() is not app:
+            ctx.with_resource(app.app_context())
+
+        return app.cli.get_command(ctx, name)
 
     def list_commands(self, ctx):
         self._load_plugin_commands()
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 7a8e9af9..7d83d865 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -13,6 +13,7 @@ import pytest
 from _pytest.monkeypatch import notset
 from click.testing import CliRunner
 
+from flask import _app_ctx_stack
 from flask import Blueprint
 from flask import current_app
 from flask import Flask
@@ -310,6 +311,26 @@ def test_lazy_load_error(monkeypatch):
             lazy._flush_bg_loading_exception()
 
 
+def test_app_cli_has_app_context(app, runner):
+    def _param_cb(ctx, param, value):
+        # current_app should be available in parameter callbacks
+        return bool(current_app)
+
+    @app.cli.command()
+    @click.argument("value", callback=_param_cb)
+    def check(value):
+        app = click.get_current_context().obj.load_app()
+        # the loaded app should be the same as current_app
+        same_app = current_app._get_current_object() is app
+        # only one app context should be pushed
+        stack_size = len(_app_ctx_stack._local.stack)
+        return same_app, stack_size, value
+
+    cli = FlaskGroup(create_app=lambda: app)
+    result = runner.invoke(cli, ["check", "x"], standalone_mode=False)
+    assert result.return_value == (True, 1, True)
+
+
 def test_with_appcontext(runner):
     @click.command()
     @with_appcontext
@@ -323,12 +344,12 @@ def test_with_appcontext(runner):
     assert result.output == "testapp\n"
 
 
-def test_appgroup(runner):
+def test_appgroup_app_context(runner):
     @click.group(cls=AppGroup)
     def cli():
         pass
 
-    @cli.command(with_appcontext=True)
+    @cli.command()
     def test():
         click.echo(current_app.name)
 
@@ -336,7 +357,7 @@ def test_appgroup(runner):
     def subgroup():
         pass
 
-    @subgroup.command(with_appcontext=True)
+    @subgroup.command()
     def test2():
         click.echo(current_app.name)
 
@@ -351,7 +372,7 @@ def test_appgroup(runner):
     assert result.output == "testappgroup\n"
 
 
-def test_flaskgroup(runner):
+def test_flaskgroup_app_context(runner):
     def create_app():
         return Flask("flaskgroup")