diff --git a/packages/aws-cdk/lib/cdk-toolkit.ts b/packages/aws-cdk/lib/cdk-toolkit.ts
index ed38899c79555..336f93e225b2c 100644
--- a/packages/aws-cdk/lib/cdk-toolkit.ts
+++ b/packages/aws-cdk/lib/cdk-toolkit.ts
@@ -615,9 +615,7 @@ export class CdkToolkit {
     const rootDir = path.dirname(path.resolve(PROJECT_CONFIG));
     debug("root directory used for 'watch' is: %s", rootDir);
 
-    const watchSettings: { include?: string | string[]; exclude: string | string[] } | undefined =
-      this.props.configuration.settings.get(['watch']);
-    if (!watchSettings) {
+    if (options.include === undefined && options.exclude === undefined) {
       throw new ToolkitError(
         "Cannot use the 'watch' command without specifying at least one directory to monitor. " +
           'Make sure to add a "watch" key to your cdk.json',
@@ -629,7 +627,7 @@ export class CdkToolkit {
     // 2. "watch" setting without an "include" key? We default to observing "./**".
     // 3. "watch" setting with an empty "include" key? We default to observing "./**".
     // 4. Non-empty "include" key? Just use the "include" key.
-    const watchIncludes = this.patternsArrayForWatch(watchSettings.include, {
+    const watchIncludes = this.patternsArrayForWatch(options.include, {
       rootDir,
       returnRootDirIfEmpty: true,
     });
@@ -641,11 +639,11 @@ export class CdkToolkit {
     // 2. Any file whose name starts with a dot.
     // 3. Any directory's content whose name starts with a dot.
     // 4. Any node_modules and its content (even if it's not a JS/TS project, you might be using a local aws-cli package)
-    const outputDir = this.props.configuration.settings.get(['globalOptions', 'output']);
-    const watchExcludes = this.patternsArrayForWatch(watchSettings.exclude, {
+    const output = options.output ?? 'cdk.out';
+    const watchExcludes = this.patternsArrayForWatch(options.exclude, {
       rootDir,
       returnRootDirIfEmpty: false,
-    }).concat(`${outputDir}/**`, '**/.*', '**/.*/**', '**/node_modules/**');
+    }).concat(`${output}/**`, '**/.*', '**/.*/**', '**/node_modules/**');
     debug("'exclude' patterns for 'watch': %s", watchExcludes);
 
     // Since 'cdk deploy' is a relatively slow operation for a 'watch' process,
@@ -1522,6 +1520,27 @@ interface WatchOptions extends Omit<CfnDeployOptions, 'execute'> {
    * @default 1
    */
   readonly concurrency?: number;
+
+  /**
+   * Path where the CloudAssembly is located
+   *
+   * @default 'cdk.out'
+   */
+  readonly output?: string;
+
+  /**
+   * Include these patterns in watch
+   *
+   * @default []
+   */
+  readonly include?: string[];
+
+  /**
+   * Exclude these patterns from watch
+   *
+   * @default []
+   */
+  readonly exclude?: string[];
 }
 
 export interface DeployOptions extends CfnDeployOptions, WatchOptions {
diff --git a/packages/aws-cdk/lib/cli.ts b/packages/aws-cdk/lib/cli.ts
index c0110ebe2ecb0..a960ca2bbada2 100644
--- a/packages/aws-cdk/lib/cli.ts
+++ b/packages/aws-cdk/lib/cli.ts
@@ -354,6 +354,8 @@ export async function exec(args: string[], synthesizer?: Synthesizer): Promise<n
             ? AssetBuildTime.ALL_BEFORE_DEPLOY
             : AssetBuildTime.JUST_IN_TIME,
           ignoreNoStacks: deployOptions.ignoreNoStacks,
+          include: deployOptions.include,
+          exclude: deployOptions.exclude,
         });
 
       case 'rollback':
@@ -390,6 +392,7 @@ export async function exec(args: string[], synthesizer?: Synthesizer): Promise<n
         return cli.watch({
           selector: createSelector(watchOptions.STACKS),
           exclusively: watchOptions.exclusively,
+          output: globalOptions.output,
           toolkitStackName,
           roleArn: globalOptions.roleArn,
           reuseAssets: watchOptions.buildExclude,
@@ -403,6 +406,8 @@ export async function exec(args: string[], synthesizer?: Synthesizer): Promise<n
           hotswap: determineHotswapMode(watchOptions.hotswap, watchOptions.hotswapFallback, true),
           traceLogs: watchOptions.logs,
           concurrency: watchOptions.concurrency,
+          include: watchOptions.include,
+          exclude: watchOptions.exclude,
         });
 
       case 'destroy':
diff --git a/packages/aws-cdk/lib/config.ts b/packages/aws-cdk/lib/config.ts
index 2ef82baf3304e..367251d656a5e 100644
--- a/packages/aws-cdk/lib/config.ts
+++ b/packages/aws-cdk/lib/config.ts
@@ -163,6 +163,8 @@ export async function makeConfig(): Promise<CliConfig> {
               'and deploy the given stack(s) automatically when changes are detected. ' +
               'Implies --hotswap by default',
           },
+          'include': { type: 'array', desc: 'Watch files with these patterns', default: [] },
+          'exclude': { type: 'array', desc: 'Do not watch files with these patterns', default: [] },
           'logs': {
             type: 'boolean',
             default: true,
@@ -249,6 +251,8 @@ export async function makeConfig(): Promise<CliConfig> {
           variadic: true,
         },
         options: {
+          'include': { type: 'array', desc: 'Include files with these patterns', default: [] },
+          'exclude': { type: 'array', desc: 'Exclude files with these patterns', default: [] },
           'build-exclude': { type: 'array', alias: 'E', desc: 'Do not rebuild asset with the given ID. Can be specified multiple times', default: [] },
           'exclusively': { type: 'boolean', alias: 'e', desc: 'Only deploy requested stacks, don\'t include dependencies' },
           'change-set-name': { type: 'string', desc: 'Name of the CloudFormation change set to create' },
diff --git a/packages/aws-cdk/lib/convert-to-user-input.ts b/packages/aws-cdk/lib/convert-to-user-input.ts
index cb103b8f65f5c..dedd6d875fd1b 100644
--- a/packages/aws-cdk/lib/convert-to-user-input.ts
+++ b/packages/aws-cdk/lib/convert-to-user-input.ts
@@ -114,6 +114,8 @@ export function convertYargsToUserInput(args: any): UserInput {
         hotswap: args.hotswap,
         hotswapFallback: args.hotswapFallback,
         watch: args.watch,
+        include: args.include,
+        exclude: args.exclude,
         logs: args.logs,
         concurrency: args.concurrency,
         assetParallelism: args.assetParallelism,
@@ -149,6 +151,8 @@ export function convertYargsToUserInput(args: any): UserInput {
 
     case 'watch':
       commandOptions = {
+        include: args.include,
+        exclude: args.exclude,
         buildExclude: args.buildExclude,
         exclusively: args.exclusively,
         changeSetName: args.changeSetName,
@@ -346,6 +350,8 @@ export function convertConfigToUserInput(config: any): UserInput {
     hotswap: config.deploy?.hotswap,
     hotswapFallback: config.deploy?.hotswapFallback,
     watch: config.deploy?.watch,
+    include: Array.isArray(config.deploy?.include) ? config.deploy?.include : [config.deploy?.include],
+    exclude: Array.isArray(config.deploy?.exclude) ? config.deploy?.exclude : [config.deploy?.exclude],
     logs: config.deploy?.logs,
     concurrency: config.deploy?.concurrency,
     assetParallelism: config.deploy?.assetParallelism,
@@ -369,6 +375,8 @@ export function convertConfigToUserInput(config: any): UserInput {
     resourceMapping: config.import?.resourceMapping,
   };
   const watchOptions = {
+    include: Array.isArray(config.watch?.include) ? config.watch?.include : [config.watch?.include],
+    exclude: Array.isArray(config.watch?.exclude) ? config.watch?.exclude : [config.watch?.exclude],
     buildExclude: config.watch?.buildExclude,
     exclusively: config.watch?.exclusively,
     changeSetName: config.watch?.changeSetName,
diff --git a/packages/aws-cdk/lib/parse-command-line-arguments.ts b/packages/aws-cdk/lib/parse-command-line-arguments.ts
index 20b09694290fa..a3750237c72ad 100644
--- a/packages/aws-cdk/lib/parse-command-line-arguments.ts
+++ b/packages/aws-cdk/lib/parse-command-line-arguments.ts
@@ -465,6 +465,20 @@ export function parseCommandLineArguments(args: Array<string>): any {
           type: 'boolean',
           desc: 'Continuously observe the project files, and deploy the given stack(s) automatically when changes are detected. Implies --hotswap by default',
         })
+        .option('include', {
+          default: [],
+          type: 'array',
+          desc: 'Watch files with these patterns',
+          nargs: 1,
+          requiresArg: true,
+        })
+        .option('exclude', {
+          default: [],
+          type: 'array',
+          desc: 'Do not watch files with these patterns',
+          nargs: 1,
+          requiresArg: true,
+        })
         .option('logs', {
           default: true,
           type: 'boolean',
@@ -570,6 +584,20 @@ export function parseCommandLineArguments(args: Array<string>): any {
     )
     .command('watch [STACKS..]', "Shortcut for 'deploy --watch'", (yargs: Argv) =>
       yargs
+        .option('include', {
+          default: [],
+          type: 'array',
+          desc: 'Include files with these patterns',
+          nargs: 1,
+          requiresArg: true,
+        })
+        .option('exclude', {
+          default: [],
+          type: 'array',
+          desc: 'Exclude files with these patterns',
+          nargs: 1,
+          requiresArg: true,
+        })
         .option('build-exclude', {
           default: [],
           type: 'array',
diff --git a/packages/aws-cdk/lib/user-input.ts b/packages/aws-cdk/lib/user-input.ts
index 03342227148fe..02ec356e1d4a7 100644
--- a/packages/aws-cdk/lib/user-input.ts
+++ b/packages/aws-cdk/lib/user-input.ts
@@ -734,6 +734,20 @@ export interface DeployOptions {
    */
   readonly watch?: boolean;
 
+  /**
+   * Watch files with these patterns
+   *
+   * @default - []
+   */
+  readonly include?: Array<string>;
+
+  /**
+   * Do not watch files with these patterns
+   *
+   * @default - []
+   */
+  readonly exclude?: Array<string>;
+
   /**
    * Show CloudWatch log events from all resources in the selected Stacks in the terminal. 'true' by default, use --no-logs to turn off. Only in effect if specified alongside the '--watch' option
    *
@@ -897,6 +911,20 @@ export interface ImportOptions {
  * @struct
  */
 export interface WatchOptions {
+  /**
+   * Include files with these patterns
+   *
+   * @default - []
+   */
+  readonly include?: Array<string>;
+
+  /**
+   * Exclude files with these patterns
+   *
+   * @default - []
+   */
+  readonly exclude?: Array<string>;
+
   /**
    * Do not rebuild asset with the given ID. Can be specified multiple times
    *
diff --git a/packages/aws-cdk/test/cdk-toolkit.test.ts b/packages/aws-cdk/test/cdk-toolkit.test.ts
index 8dad7142baea7..2a4ae902906fa 100644
--- a/packages/aws-cdk/test/cdk-toolkit.test.ts
+++ b/packages/aws-cdk/test/cdk-toolkit.test.ts
@@ -92,6 +92,7 @@ import { CdkToolkit, markTesting, Tag } from '../lib/cdk-toolkit';
 import { RequireApproval } from '../lib/diff';
 import { Configuration } from '../lib/settings';
 import { flatten } from '../lib/util';
+import { convertConfigToUserInput } from '../lib/convert-to-user-input';
 
 markTesting();
 
@@ -971,12 +972,12 @@ describe('watch', () => {
   });
 
   test('observes only the root directory by default', async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {});
     const toolkit = defaultToolkitSetup();
 
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      include: [],
     });
 
     const includeArgs = fakeChokidarWatch.includeArgs;
@@ -984,55 +985,59 @@ describe('watch', () => {
   });
 
   test("allows providing a single string in 'watch.include'", async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {
-      include: 'my-dir',
+    const userInput = convertConfigToUserInput({
+      watch: {
+        include: 'my-dir',
+      },
     });
     const toolkit = defaultToolkitSetup();
 
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      include: userInput.watch?.include,
     });
 
     expect(fakeChokidarWatch.includeArgs).toStrictEqual(['my-dir']);
   });
 
   test("allows providing an array of strings in 'watch.include'", async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {
-      include: ['my-dir1', '**/my-dir2/*'],
-    });
     const toolkit = defaultToolkitSetup();
 
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      include: ['my-dir1', '**/my-dir2/*'],
     });
 
     expect(fakeChokidarWatch.includeArgs).toStrictEqual(['my-dir1', '**/my-dir2/*']);
   });
 
   test('ignores the output dir, dot files, dot directories, and node_modules by default', async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {});
-    cloudExecutable.configuration.settings.set(['output'], 'cdk.out');
     const toolkit = defaultToolkitSetup();
 
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      include: [],
+      output: 'cdk.out',
     });
 
     expect(fakeChokidarWatch.excludeArgs).toStrictEqual(['cdk.out/**', '**/.*', '**/.*/**', '**/node_modules/**']);
   });
 
   test("allows providing a single string in 'watch.exclude'", async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {
-      exclude: 'my-dir',
+    const userInput = convertConfigToUserInput({
+      watch: {
+        exclude: 'my-dir',
+      },
     });
     const toolkit = defaultToolkitSetup();
 
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      exclude: userInput.watch?.exclude,
     });
 
     const excludeArgs = fakeChokidarWatch.excludeArgs;
@@ -1041,14 +1046,12 @@ describe('watch', () => {
   });
 
   test("allows providing an array of strings in 'watch.exclude'", async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {
-      exclude: ['my-dir1', '**/my-dir2'],
-    });
     const toolkit = defaultToolkitSetup();
 
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      exclude: ['my-dir1', '**/my-dir2'],
     });
 
     const excludeArgs = fakeChokidarWatch.excludeArgs;
@@ -1058,7 +1061,6 @@ describe('watch', () => {
   });
 
   test('allows watching with deploy concurrency', async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {});
     const toolkit = defaultToolkitSetup();
     const cdkDeployMock = jest.fn();
     toolkit.deploy = cdkDeployMock;
@@ -1067,6 +1069,7 @@ describe('watch', () => {
       selector: { patterns: [] },
       concurrency: 3,
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      include: [],
     });
     fakeChokidarWatcherOn.readyCallback();
 
@@ -1075,7 +1078,6 @@ describe('watch', () => {
 
   describe.each([HotswapMode.FALL_BACK, HotswapMode.HOTSWAP_ONLY])('%p mode', (hotswapMode) => {
     test('passes through the correct hotswap mode to deployStack()', async () => {
-      cloudExecutable.configuration.settings.set(['watch'], {});
       const toolkit = defaultToolkitSetup();
       const cdkDeployMock = jest.fn();
       toolkit.deploy = cdkDeployMock;
@@ -1083,6 +1085,7 @@ describe('watch', () => {
       await toolkit.watch({
         selector: { patterns: [] },
         hotswap: hotswapMode,
+        include: [],
       });
       fakeChokidarWatcherOn.readyCallback();
 
@@ -1091,7 +1094,6 @@ describe('watch', () => {
   });
 
   test('respects HotswapMode.HOTSWAP_ONLY', async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {});
     const toolkit = defaultToolkitSetup();
     const cdkDeployMock = jest.fn();
     toolkit.deploy = cdkDeployMock;
@@ -1099,6 +1101,7 @@ describe('watch', () => {
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.HOTSWAP_ONLY,
+      include: [],
     });
     fakeChokidarWatcherOn.readyCallback();
 
@@ -1106,7 +1109,6 @@ describe('watch', () => {
   });
 
   test('respects HotswapMode.FALL_BACK', async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {});
     const toolkit = defaultToolkitSetup();
     const cdkDeployMock = jest.fn();
     toolkit.deploy = cdkDeployMock;
@@ -1114,6 +1116,7 @@ describe('watch', () => {
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.FALL_BACK,
+      include: [],
     });
     fakeChokidarWatcherOn.readyCallback();
 
@@ -1121,7 +1124,6 @@ describe('watch', () => {
   });
 
   test('respects HotswapMode.FULL_DEPLOYMENT', async () => {
-    cloudExecutable.configuration.settings.set(['watch'], {});
     const toolkit = defaultToolkitSetup();
     const cdkDeployMock = jest.fn();
     toolkit.deploy = cdkDeployMock;
@@ -1129,6 +1131,7 @@ describe('watch', () => {
     await toolkit.watch({
       selector: { patterns: [] },
       hotswap: HotswapMode.FULL_DEPLOYMENT,
+      include: [],
     });
     fakeChokidarWatcherOn.readyCallback();
 
@@ -1140,13 +1143,13 @@ describe('watch', () => {
     let cdkDeployMock: jest.Mock;
 
     beforeEach(async () => {
-      cloudExecutable.configuration.settings.set(['watch'], {});
       toolkit = defaultToolkitSetup();
       cdkDeployMock = jest.fn();
       toolkit.deploy = cdkDeployMock;
       await toolkit.watch({
         selector: { patterns: [] },
         hotswap: HotswapMode.HOTSWAP_ONLY,
+        include: [],
       });
     });
 
diff --git a/tools/@aws-cdk/user-input-gen/lib/convert-to-user-input-gen.ts b/tools/@aws-cdk/user-input-gen/lib/convert-to-user-input-gen.ts
index c7dc010328864..969a461808b52 100644
--- a/tools/@aws-cdk/user-input-gen/lib/convert-to-user-input-gen.ts
+++ b/tools/@aws-cdk/user-input-gen/lib/convert-to-user-input-gen.ts
@@ -123,8 +123,18 @@ function buildCommandOptions(options: CliAction, argName: string, prefix?: strin
   const commandOptions: string[] = [];
   for (const optionName of Object.keys(options.options ?? {})) {
     const name = kebabToCamelCase(optionName);
+
     if (prefix) {
-      commandOptions.push(`'${name}': ${argName}.${prefix}?.${name},`);
+      const rhs = `${argName}.${prefix}?.${name}`;
+
+      // For legacy reasons, `watch.include` and `watch.exclude` are special cases where strings
+      // are allowed in place of string arrays. We therefore need to do the conversion only on
+      // the config function to be backwards compatible.
+      if (argName == CONFIG_ARG_NAME && (name == 'include' || name == 'exclude')) {
+        commandOptions.push(`'${name}': Array.isArray(${rhs}) ? ${rhs} : [${rhs}],`);
+      } else {
+        commandOptions.push(`'${name}': ${rhs},`);
+      }
     } else {
       commandOptions.push(`'${name}': ${argName}.${name},`);
     }