[tool] Add Android dependency (gradle) option to update dependencies command (#4757)

Adds an `android-dependency` option to the `update-dependency` command such that you can update Android dependencies provided the dependency and a version across relevant plugins. This PR specifically adds support for the Gradle dependency, relevant to plugin example apps.

Running the command looks like:
```
dart run script/tool/bin/flutter_plugin_tools.dart update-dependency --android-dependency gradle --version 1.2.3
```
diff --git a/script/tool/lib/src/update_dependency_command.dart b/script/tool/lib/src/update_dependency_command.dart
index 7f7c3c6..185abb5 100644
--- a/script/tool/lib/src/update_dependency_command.dart
+++ b/script/tool/lib/src/update_dependency_command.dart
@@ -19,6 +19,7 @@
 
 const int _exitIncorrectTargetDependency = 3;
 const int _exitNoTargetVersion = 4;
+const int _exitInvalidTargetVersion = 5;
 
 /// A command to update a dependency in packages.
 ///
@@ -38,6 +39,14 @@
       _pubPackageFlag,
       help: 'A pub package to update.',
     );
+    argParser.addOption(_androidDependency,
+        help: 'An Android dependency to update.',
+        allowed: <String>[
+          'gradle',
+        ],
+        allowedHelp: <String, String>{
+          'gradle': 'Updates Gradle version used in plugin example apps.',
+        });
     argParser.addOption(
       _versionFlag,
       help: 'The version to update to.\n\n'
@@ -45,16 +54,19 @@
           'provided. This can be any constraint that pubspec.yaml allows; a '
           'specific version will be treated as the exact version for '
           'dependencies that are alread pinned, or a ^ range for those that '
-          'are unpinned.',
+          'are unpinned.\n'
+          '- For Android dependencies, a version must be provided.',
     );
   }
 
   static const String _pubPackageFlag = 'pub-package';
+  static const String _androidDependency = 'android-dependency';
   static const String _versionFlag = 'version';
 
   final PubVersionFinder _pubVersionFinder;
 
   late final String? _targetPubPackage;
+  late final String? _targetAndroidDependency;
   late final String _targetVersion;
 
   @override
@@ -72,7 +84,10 @@
 
   @override
   Future<void> initializeRun() async {
-    const Set<String> targetFlags = <String>{_pubPackageFlag};
+    const Set<String> targetFlags = <String>{
+      _pubPackageFlag,
+      _androidDependency
+    };
     final Set<String> passedTargetFlags =
         targetFlags.where((String flag) => argResults![flag] != null).toSet();
     if (passedTargetFlags.length != 1) {
@@ -80,6 +95,8 @@
           'Exactly one of the target flags must be provided: (${targetFlags.join(', ')})');
       throw ToolExit(_exitIncorrectTargetDependency);
     }
+
+    // Setup for updating pub dependency.
     _targetPubPackage = getNullableStringArg(_pubPackageFlag);
     if (_targetPubPackage != null) {
       final String? version = getNullableStringArg(_versionFlag);
@@ -102,6 +119,33 @@
         }
       } else {
         _targetVersion = version;
+        return;
+      }
+    }
+
+    // Setup for updating Android dependency.
+    _targetAndroidDependency = getNullableStringArg(_androidDependency);
+    if (_targetAndroidDependency != null) {
+      final String? version = getNullableStringArg(_versionFlag);
+      if (version == null) {
+        printError('A version must be provided to update this dependency.');
+        throw ToolExit(_exitNoTargetVersion);
+      } else if (_targetAndroidDependency == 'gradle') {
+        final RegExp validGradleVersionPattern = RegExp(r'^\d+(?:\.\d+){1,2}$');
+        final bool isValidGradleVersion =
+            validGradleVersionPattern.stringMatch(version) == version;
+        if (!isValidGradleVersion) {
+          printError(
+              'A version with a valid format (maximum 2-3 numbers separated by period) must be provided.');
+          throw ToolExit(_exitInvalidTargetVersion);
+        }
+        _targetVersion = version;
+        return;
+      } else {
+        // TODO(camsim99): Add other supported Android dependencies like the Android SDK and AGP.
+        printError(
+            'Target Android dependency $_targetAndroidDependency is unrecognized.');
+        throw ToolExit(_exitIncorrectTargetDependency);
       }
     }
   }
@@ -116,7 +160,11 @@
     if (_targetPubPackage != null) {
       return _runForPubDependency(package, _targetPubPackage!);
     }
-    // TODO(stuartmorgan): Add othe dependency types here (e.g., maven).
+    if (_targetAndroidDependency != null) {
+      return _runForAndroidDependency(package);
+    }
+
+    // TODO(stuartmorgan): Add other dependency types here (e.g., maven).
 
     return PackageResult.fail();
   }
@@ -181,6 +229,65 @@
     return PackageResult.success();
   }
 
+  /// Handles all of the updates for [package] when the target dependency is
+  /// an Android dependency.
+  Future<PackageResult> _runForAndroidDependency(
+      RepositoryPackage package) async {
+    if (_targetAndroidDependency == 'gradle') {
+      final Iterable<RepositoryPackage> packageExamples = package.getExamples();
+      bool updateRanForExamples = false;
+      for (final RepositoryPackage example in packageExamples) {
+        if (!example.platformDirectory(FlutterPlatform.android).existsSync()) {
+          continue;
+        }
+
+        updateRanForExamples = true;
+        Directory gradleWrapperPropertiesDirectory =
+            example.platformDirectory(FlutterPlatform.android);
+        if (gradleWrapperPropertiesDirectory
+            .childDirectory('app')
+            .childDirectory('gradle')
+            .existsSync()) {
+          gradleWrapperPropertiesDirectory =
+              gradleWrapperPropertiesDirectory.childDirectory('app');
+        }
+        final File gradleWrapperPropertiesFile =
+            gradleWrapperPropertiesDirectory
+                .childDirectory('gradle')
+                .childDirectory('wrapper')
+                .childFile('gradle-wrapper.properties');
+
+        final String gradleWrapperPropertiesContents =
+            gradleWrapperPropertiesFile.readAsStringSync();
+        final RegExp validGradleDistributionUrl =
+            RegExp(r'^\s*distributionUrl\s*=\s*.*\.zip', multiLine: true);
+        if (!validGradleDistributionUrl
+            .hasMatch(gradleWrapperPropertiesContents)) {
+          return PackageResult.fail(<String>[
+            'Unable to find a "distributionUrl" entry to update for ${package.displayName}.'
+          ]);
+        }
+
+        print(
+            '${indentation}Updating ${getRelativePosixPath(example.directory, from: package.directory)} to "$_targetVersion"');
+        final String newGradleWrapperPropertiesContents =
+            gradleWrapperPropertiesContents.replaceFirst(
+                validGradleDistributionUrl,
+                'distributionUrl=https\\://services.gradle.org/distributions/gradle-$_targetVersion-all.zip');
+        // TODO(camsim99): Validate current AGP version against target Gradle
+        // version: https://github.com/flutter/flutter/issues/133887.
+        gradleWrapperPropertiesFile
+            .writeAsStringSync(newGradleWrapperPropertiesContents);
+      }
+      return updateRanForExamples
+          ? PackageResult.success()
+          : PackageResult.skip('No example apps run on Android.');
+    }
+    return PackageResult.fail(<String>[
+      'Target Android dependency $_androidDependency is unrecognized.'
+    ]);
+  }
+
   /// Returns information about the current dependency of [package] on
   /// the package named [dependencyName], or null if there is no dependency.
   _PubDependencyInfo? _getPubDependencyInfo(
diff --git a/script/tool/test/update_dependency_command_test.dart b/script/tool/test/update_dependency_command_test.dart
index e27b444..0fd3969 100644
--- a/script/tool/test/update_dependency_command_test.dart
+++ b/script/tool/test/update_dependency_command_test.dart
@@ -79,6 +79,27 @@
     );
   });
 
+  test('throws if multiple dependencies specified', () async {
+    Error? commandError;
+    final List<String> output = await runCapturingPrint(runner, <String>[
+      'update-dependency',
+      '--pub-package',
+      'target_package',
+      '--android-dependency',
+      'gradle'
+    ], errorHandler: (Error e) {
+      commandError = e;
+    });
+
+    expect(commandError, isA<ToolExit>());
+    expect(
+      output,
+      containsAllInOrder(<Matcher>[
+        contains('Exactly one of the target flags must be provided:'),
+      ]),
+    );
+  });
+
   group('pub dependencies', () {
     test('throws if no version is given for an unpublished target', () async {
       mockHttpResponse = (http.Request request) async {
@@ -584,4 +605,226 @@
       );
     });
   });
+
+  group('Android dependencies', () {
+    group('gradle', () {
+      test('throws if version format is invalid', () async {
+        Error? commandError;
+        final List<String> output = await runCapturingPrint(runner, <String>[
+          'update-dependency',
+          '--android-dependency',
+          'gradle',
+          '--version',
+          '83',
+        ], errorHandler: (Error e) {
+          commandError = e;
+        });
+
+        expect(commandError, isA<ToolExit>());
+        expect(
+          output,
+          containsAllInOrder(<Matcher>[
+            contains(
+                'A version with a valid format (maximum 2-3 numbers separated by period) must be provided.'),
+          ]),
+        );
+      });
+
+      test('skips if example app does not run on Android', () async {
+        final RepositoryPackage package =
+            createFakePlugin('fake_plugin', packagesDir);
+
+        final List<String> output = await runCapturingPrint(runner, <String>[
+          'update-dependency',
+          '--packages',
+          package.displayName,
+          '--android-dependency',
+          'gradle',
+          '--version',
+          '8.8.8',
+        ]);
+
+        expect(
+          output,
+          containsAllInOrder(<Matcher>[
+            contains('SKIPPING: No example apps run on Android.'),
+          ]),
+        );
+      });
+
+      test(
+          'throws if wrapper does not have distribution URL with expected format',
+          () async {
+        final RepositoryPackage package = createFakePlugin(
+            'fake_plugin', packagesDir, extraFiles: <String>[
+          'example/android/app/gradle/wrapper/gradle-wrapper.properties'
+        ]);
+
+        final File gradleWrapperPropertiesFile = package.directory
+            .childDirectory('example')
+            .childDirectory('android')
+            .childDirectory('app')
+            .childDirectory('gradle')
+            .childDirectory('wrapper')
+            .childFile('gradle-wrapper.properties');
+
+        gradleWrapperPropertiesFile.writeAsStringSync('''
+How is it even possible that I didn't specify a Gradle distribution?
+''');
+
+        Error? commandError;
+        final List<String> output = await runCapturingPrint(runner, <String>[
+          'update-dependency',
+          '--packages',
+          package.displayName,
+          '--android-dependency',
+          'gradle',
+          '--version',
+          '8.8.8',
+        ], errorHandler: (Error e) {
+          commandError = e;
+        });
+
+        expect(commandError, isA<ToolExit>());
+        expect(
+          output,
+          containsAllInOrder(<Matcher>[
+            contains(
+                'Unable to find a "distributionUrl" entry to update for ${package.displayName}.'),
+          ]),
+        );
+      });
+
+      test('succeeds if example app has android/app/gradle directory structure',
+          () async {
+        final RepositoryPackage package = createFakePlugin(
+            'fake_plugin', packagesDir, extraFiles: <String>[
+          'example/android/app/gradle/wrapper/gradle-wrapper.properties'
+        ]);
+        const String newGradleVersion = '8.8.8';
+
+        final File gradleWrapperPropertiesFile = package.directory
+            .childDirectory('example')
+            .childDirectory('android')
+            .childDirectory('app')
+            .childDirectory('gradle')
+            .childDirectory('wrapper')
+            .childFile('gradle-wrapper.properties');
+
+        gradleWrapperPropertiesFile.writeAsStringSync(r'''
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
+distributionUrl=https\://services.gradle.org/distributions/gradle-7.6.1-all.zip
+''');
+
+        await runCapturingPrint(runner, <String>[
+          'update-dependency',
+          '--packages',
+          package.displayName,
+          '--android-dependency',
+          'gradle',
+          '--version',
+          newGradleVersion,
+        ]);
+
+        final String updatedGradleWrapperPropertiesContents =
+            gradleWrapperPropertiesFile.readAsStringSync();
+        expect(
+            updatedGradleWrapperPropertiesContents,
+            contains(
+                r'distributionUrl=https\://services.gradle.org/distributions/'
+                'gradle-$newGradleVersion-all.zip'));
+      });
+
+      test('succeeds if example app has android/gradle directory structure',
+          () async {
+        final RepositoryPackage package = createFakePlugin(
+            'fake_plugin', packagesDir, extraFiles: <String>[
+          'example/android/gradle/wrapper/gradle-wrapper.properties'
+        ]);
+        const String newGradleVersion = '9.9';
+
+        final File gradleWrapperPropertiesFile = package.directory
+            .childDirectory('example')
+            .childDirectory('android')
+            .childDirectory('gradle')
+            .childDirectory('wrapper')
+            .childFile('gradle-wrapper.properties');
+
+        gradleWrapperPropertiesFile.writeAsStringSync(r'''
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
+distributionUrl=https\://services.gradle.org/distributions/gradle-7.6.1-all.zip
+''');
+
+        await runCapturingPrint(runner, <String>[
+          'update-dependency',
+          '--packages',
+          package.displayName,
+          '--android-dependency',
+          'gradle',
+          '--version',
+          newGradleVersion,
+        ]);
+
+        final String updatedGradleWrapperPropertiesContents =
+            gradleWrapperPropertiesFile.readAsStringSync();
+        expect(
+            updatedGradleWrapperPropertiesContents,
+            contains(
+                r'distributionUrl=https\://services.gradle.org/distributions/'
+                'gradle-$newGradleVersion-all.zip'));
+      });
+    });
+  });
+
+  test('succeeds if one example app runs on Android and another does not',
+      () async {
+    final RepositoryPackage package = createFakePlugin(
+        'fake_plugin', packagesDir, examples: <String>[
+      'example_1',
+      'example_2'
+    ], extraFiles: <String>[
+      'example/example_2/android/app/gradle/wrapper/gradle-wrapper.properties'
+    ]);
+    const String newGradleVersion = '8.8.8';
+
+    final File gradleWrapperPropertiesFile = package.directory
+        .childDirectory('example')
+        .childDirectory('example_2')
+        .childDirectory('android')
+        .childDirectory('app')
+        .childDirectory('gradle')
+        .childDirectory('wrapper')
+        .childFile('gradle-wrapper.properties');
+
+    gradleWrapperPropertiesFile.writeAsStringSync(r'''
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
+distributionUrl=https\://services.gradle.org/distributions/gradle-7.6.1-all.zip
+''');
+
+    await runCapturingPrint(runner, <String>[
+      'update-dependency',
+      '--packages',
+      package.displayName,
+      '--android-dependency',
+      'gradle',
+      '--version',
+      newGradleVersion,
+    ]);
+
+    final String updatedGradleWrapperPropertiesContents =
+        gradleWrapperPropertiesFile.readAsStringSync();
+    expect(
+        updatedGradleWrapperPropertiesContents,
+        contains(r'distributionUrl=https\://services.gradle.org/distributions/'
+            'gradle-$newGradleVersion-all.zip'));
+  });
 }