diff --git a/lib/src/command_runner.dart b/lib/src/command_runner.dart
index 91d0d9e09..f2b89cf2c 100644
--- a/lib/src/command_runner.dart
+++ b/lib/src/command_runner.dart
@@ -3,6 +3,7 @@ import 'package:args/command_runner.dart';
 import 'package:io/ansi.dart';
 import 'package:io/io.dart';
 import 'package:mason/mason.dart';
+import 'package:pub_updater/pub_updater.dart';
 import 'package:usage/usage_io.dart';
 import 'package:very_good_cli/src/commands/commands.dart';
 import 'package:very_good_cli/src/version.dart';
@@ -13,15 +14,22 @@ const _gaTrackingId = 'UA-117465969-4';
 // The Google Analytics Application Name.
 const _gaAppName = 'very-good-cli';
 
+/// The package name.
+const packageName = 'very_good_cli';
+
 /// {@template very_good_command_runner}
 /// A [CommandRunner] for the Very Good CLI.
 /// {@endtemplate}
 class VeryGoodCommandRunner extends CommandRunner<int> {
   /// {@macro very_good_command_runner}
-  VeryGoodCommandRunner({Analytics? analytics, Logger? logger})
-      : _logger = logger ?? Logger(),
+  VeryGoodCommandRunner({
+    Analytics? analytics,
+    Logger? logger,
+    PubUpdater? pubUpdater,
+  })  : _logger = logger ?? Logger(),
         _analytics =
             analytics ?? AnalyticsIO(_gaTrackingId, _gaAppName, packageVersion),
+        _pubUpdater = pubUpdater ?? PubUpdater(),
         super('very_good', '🦄 A Very Good Command Line Interface') {
     argParser
       ..addFlag(
@@ -46,6 +54,7 @@ class VeryGoodCommandRunner extends CommandRunner<int> {
 
   final Logger _logger;
   final Analytics _analytics;
+  final PubUpdater _pubUpdater;
 
   @override
   Future<int> run(Iterable<String> args) async {
@@ -85,6 +94,7 @@ class VeryGoodCommandRunner extends CommandRunner<int> {
 
   @override
   Future<int?> runCommand(ArgResults topLevelResults) async {
+    await _checkForUpdates();
     if (topLevelResults['version'] == true) {
       _logger.info('very_good version: $packageVersion');
       return ExitCode.success.code;
@@ -97,4 +107,32 @@ class VeryGoodCommandRunner extends CommandRunner<int> {
     }
     return super.runCommand(topLevelResults);
   }
+
+  Future<void> _checkForUpdates() async {
+    try {
+      final isUpToDate = await _pubUpdater.isUpToDate(
+        packageName: packageName,
+        currentVersion: packageVersion,
+      );
+
+      if (!isUpToDate) {
+        _logger.info(
+          lightYellow.wrap('A new release of $packageName is available.'),
+        );
+        final response = _logger.prompt('Would you like to update? (y/n) ');
+        if (response.isYes()) {
+          final done = _logger.progress('Updating');
+          await _pubUpdater.update(packageName: packageName);
+          done('Updated!');
+        }
+      }
+    } catch (_) {}
+  }
+}
+
+extension on String {
+  bool isYes() {
+    final normalized = toLowerCase().trim();
+    return normalized == 'y' || normalized == 'yes';
+  }
 }
diff --git a/pubspec.yaml b/pubspec.yaml
index 0b631692c..8288a65da 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -12,6 +12,7 @@ dependencies:
   mason: ^0.0.1-dev.46
   meta: ^1.3.0
   path: ^1.8.0
+  pub_updater: ^0.1.0
   universal_io: ^2.0.4
   usage: ^4.0.2
   very_good_analysis: ^2.3.0
diff --git a/test/src/command_runner_test.dart b/test/src/command_runner_test.dart
index f0ba26e57..ee7857cf4 100644
--- a/test/src/command_runner_test.dart
+++ b/test/src/command_runner_test.dart
@@ -2,10 +2,13 @@
 import 'dart:async';
 
 import 'package:args/command_runner.dart';
+import 'package:io/ansi.dart';
 import 'package:io/io.dart';
 import 'package:mason/mason.dart';
 import 'package:mocktail/mocktail.dart';
+import 'package:pub_updater/pub_updater.dart';
 import 'package:test/test.dart';
+import 'package:universal_io/io.dart';
 import 'package:usage/usage_io.dart';
 import 'package:very_good_cli/src/command_runner.dart';
 import 'package:very_good_cli/src/version.dart';
@@ -14,6 +17,10 @@ class MockAnalytics extends Mock implements Analytics {}
 
 class MockLogger extends Mock implements Logger {}
 
+class MockPubUpdater extends Mock implements PubUpdater {}
+
+class FakeProcessResult extends Fake implements ProcessResult {}
+
 const expectedUsage = [
   '🦄 A Very Good Command Line Interface\n'
       '\n'
@@ -34,10 +41,14 @@ const expectedUsage = [
       'Run "very_good help <command>" for more information about a command.'
 ];
 
+const responseBody =
+    '{"name": "very_good_cli", "versions": ["0.4.0", "0.3.3"]}';
+
 void main() {
   group('VeryGoodCommandRunner', () {
     late List<String> printLogs;
     late Analytics analytics;
+    late PubUpdater pubUpdater;
     late Logger logger;
     late VeryGoodCommandRunner commandRunner;
 
@@ -54,13 +65,30 @@ void main() {
       printLogs = [];
 
       analytics = MockAnalytics();
+      pubUpdater = MockPubUpdater();
+
       when(() => analytics.firstRun).thenReturn(false);
       when(() => analytics.enabled).thenReturn(false);
 
+      when(
+        () => pubUpdater.isUpToDate(
+          packageName: any(named: 'packageName'),
+          currentVersion: any(named: 'currentVersion'),
+        ),
+      ).thenAnswer((_) => Future.value(true));
+
+      when(
+        () => pubUpdater.update(
+          packageName: any(named: 'packageName'),
+        ),
+      ).thenAnswer((_) => Future.value(FakeProcessResult()));
+
       logger = MockLogger();
+
       commandRunner = VeryGoodCommandRunner(
         analytics: analytics,
         logger: logger,
+        pubUpdater: pubUpdater,
       );
     });
 
@@ -71,6 +99,57 @@ void main() {
     });
 
     group('run', () {
+      test('prompts for update when newer version exists', () async {
+        when(() => pubUpdater.isUpToDate(
+              packageName: any(named: 'packageName'),
+              currentVersion: any(named: 'currentVersion'),
+            )).thenAnswer((_) => Future.value(false));
+
+        when(() => logger.prompt(any())).thenReturn('n');
+
+        final result = await commandRunner.run(['--version']);
+        expect(result, equals(ExitCode.success.code));
+        verify(
+          () => logger.info(
+            lightYellow.wrap('A new release of $packageName is available.'),
+          ),
+        ).called(1);
+        verify(
+          () => logger.prompt('Would you like to update? (y/n) '),
+        ).called(1);
+      });
+
+      test('handles pub update errors gracefully', () async {
+        when(
+          () => pubUpdater.isUpToDate(
+            packageName: any(named: 'packageName'),
+            currentVersion: any(named: 'currentVersion'),
+          ),
+        ).thenThrow(Exception('oops'));
+
+        final result = await commandRunner.run(['--version']);
+        expect(result, equals(ExitCode.success.code));
+        verifyNever(
+          () => logger.info(
+            lightYellow.wrap('A new release of $packageName is available.'),
+          ),
+        );
+      });
+
+      test('updates on "y" response when newer version exists', () async {
+        when(() => pubUpdater.isUpToDate(
+              packageName: any(named: 'packageName'),
+              currentVersion: any(named: 'currentVersion'),
+            )).thenAnswer((_) => Future.value(false));
+
+        when(() => logger.prompt(any())).thenReturn('y');
+        when(() => logger.progress(any())).thenReturn(([String? message]) {});
+
+        final result = await commandRunner.run(['--version']);
+        expect(result, equals(ExitCode.success.code));
+        verify(() => logger.progress('Updating')).called(1);
+      });
+
       test('prompts for analytics collection on first run (y)', () async {
         when(() => analytics.firstRun).thenReturn(true);
         when(() => logger.prompt(any())).thenReturn('y');
diff --git a/test/src/commands/create_test.dart b/test/src/commands/create_test.dart
index d5dafe0dc..538107601 100644
--- a/test/src/commands/create_test.dart
+++ b/test/src/commands/create_test.dart
@@ -5,6 +5,7 @@ import 'package:io/io.dart';
 import 'package:mason/mason.dart';
 import 'package:mocktail/mocktail.dart';
 import 'package:path/path.dart' as p;
+import 'package:pub_updater/pub_updater.dart';
 import 'package:test/test.dart';
 import 'package:universal_io/io.dart';
 import 'package:usage/usage_io.dart';
@@ -45,6 +46,8 @@ class MockAnalytics extends Mock implements Analytics {}
 
 class MockLogger extends Mock implements Logger {}
 
+class MockPubUpdater extends Mock implements PubUpdater {}
+
 class MockMasonGenerator extends Mock implements MasonGenerator {}
 
 class FakeDirectoryGeneratorTarget extends Fake
@@ -56,6 +59,7 @@ void main() {
     late List<String> printLogs;
     late Analytics analytics;
     late Logger logger;
+    late PubUpdater pubUpdater;
     late VeryGoodCommandRunner commandRunner;
 
     void Function() overridePrint(void Function() fn) {
@@ -90,9 +94,20 @@ void main() {
           if (_ != null) progressLogs.add(_);
         },
       );
+
+      pubUpdater = MockPubUpdater();
+
+      when(
+        () => pubUpdater.isUpToDate(
+          packageName: any(named: 'packageName'),
+          currentVersion: any(named: 'currentVersion'),
+        ),
+      ).thenAnswer((_) => Future.value(true));
+
       commandRunner = VeryGoodCommandRunner(
         analytics: analytics,
         logger: logger,
+        pubUpdater: pubUpdater,
       );
     });