diff --git a/extensions/typescript-language-features/package.json b/extensions/typescript-language-features/package.json
index 5ee66760548..78201193e17 100644
--- a/extensions/typescript-language-features/package.json
+++ b/extensions/typescript-language-features/package.json
@@ -602,6 +602,18 @@
           "description": "%configuration.suggest.completeJSDocs%",
           "scope": "resource"
         },
+        "javascript.suggest.jsdoc.generateReturns": {
+          "type": "boolean",
+          "default": true,
+          "markdownDescription": "%configuration.suggest.jsdoc.generateReturns%",
+          "scope": "resource"
+        },
+        "typescript.suggest.jsdoc.generateReturns": {
+          "type": "boolean",
+          "default": true,
+          "markdownDescription": "%configuration.suggest.jsdoc.generateReturns%",
+          "scope": "resource"
+        },
         "typescript.locale": {
           "type": [
             "string",
diff --git a/extensions/typescript-language-features/package.nls.json b/extensions/typescript-language-features/package.nls.json
index b6407a50b37..85f9a75b507 100644
--- a/extensions/typescript-language-features/package.nls.json
+++ b/extensions/typescript-language-features/package.nls.json
@@ -68,6 +68,7 @@
 	"configuration.javascript.checkJs.experimentalDecorators.deprecation": "This setting has been deprecated in favor of `js/ts.implicitProjectConfig.experimentalDecorators`.",
 	"configuration.implicitProjectConfig.strictNullChecks": "Enable/disable [strict null checks](https://www.typescriptlang.org/tsconfig#strictNullChecks) in JavaScript and TypeScript files that are not part of a project. Existing `jsconfig.json` or `tsconfig.json` files override this setting.",
 	"configuration.implicitProjectConfig.strictFunctionTypes": "Enable/disable [strict function types](https://www.typescriptlang.org/tsconfig#strictFunctionTypes) in JavaScript and TypeScript files that are not part of a project. Existing `jsconfig.json` or `tsconfig.json` files override this setting.",
+	"configuration.suggest.jsdoc.generateReturns": "Enable/disable generating `@return` annotations for JSDoc templates. Requires using TypeScript 4.2+ in the workspace.",
 	"configuration.suggest.autoImports": "Enable/disable auto import suggestions.",
 	"taskDefinition.tsconfig.description": "The tsconfig file that defines the TS build.",
 	"javascript.suggestionActions.enabled": "Enable/disable suggestion diagnostics for JavaScript files in the editor.",
diff --git a/extensions/typescript-language-features/src/languageFeatures/fileConfigurationManager.ts b/extensions/typescript-language-features/src/languageFeatures/fileConfigurationManager.ts
index b45ad7ee380..f0c41541b76 100644
--- a/extensions/typescript-language-features/src/languageFeatures/fileConfigurationManager.ts
+++ b/extensions/typescript-language-features/src/languageFeatures/fileConfigurationManager.ts
@@ -182,6 +182,7 @@ export default class FileConfigurationManager extends Disposable {
 			allowRenameOfImportPath: true,
 			includeAutomaticOptionalChainCompletions: config.get<boolean>('suggest.includeAutomaticOptionalChainCompletions', true),
 			provideRefactorNotApplicableReason: true,
+			generateReturnInDocTemplate: config.get<boolean>('suggest.jsdoc.generateReturns', true),
 		};
 
 		return preferences;
diff --git a/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts b/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts
index 6efe472e4f9..67548f5ec19 100644
--- a/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts
+++ b/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts
@@ -9,6 +9,7 @@ import { ITypeScriptServiceClient } from '../typescriptService';
 import { conditionalRegistration, requireConfiguration } from '../utils/dependentRegistration';
 import { DocumentSelector } from '../utils/documentSelector';
 import * as typeConverters from '../utils/typeConverters';
+import FileConfigurationManager from './fileConfigurationManager';
 
 
 const localize = nls.loadMessageBundle();
@@ -37,6 +38,7 @@ class JsDocCompletionProvider implements vscode.CompletionItemProvider {
 
 	constructor(
 		private readonly client: ITypeScriptServiceClient,
+		private readonly fileConfigurationManager: FileConfigurationManager,
 	) { }
 
 	public async provideCompletionItems(
@@ -53,8 +55,12 @@ class JsDocCompletionProvider implements vscode.CompletionItemProvider {
 			return undefined;
 		}
 
-		const args = typeConverters.Position.toFileLocationRequestArgs(file, position);
-		const response = await this.client.execute('docCommentTemplate', args, token);
+		const response = await this.client.interruptGetErr(async () => {
+			await this.fileConfigurationManager.ensureConfigurationForDocument(document, token);
+
+			const args = typeConverters.Position.toFileLocationRequestArgs(file, position);
+			return this.client.execute('docCommentTemplate', args, token);
+		});
 		if (response.type !== 'response' || !response.body) {
 			return undefined;
 		}
@@ -107,6 +113,9 @@ export function templateToSnippet(template: string): vscode.SnippetString {
 		out += post + ` \${${snippetIndex++}}`;
 		return out;
 	});
+
+	template = template.replace(/\* @returns[ \t]*$/gm, `* @returns \${${snippetIndex++}}`);
+
 	return new vscode.SnippetString(template);
 }
 
@@ -114,12 +123,14 @@ export function register(
 	selector: DocumentSelector,
 	modeId: string,
 	client: ITypeScriptServiceClient,
+	fileConfigurationManager: FileConfigurationManager,
+
 ): vscode.Disposable {
 	return conditionalRegistration([
 		requireConfiguration(modeId, 'suggest.completeJSDocs')
 	], () => {
 		return vscode.languages.registerCompletionItemProvider(selector.syntax,
-			new JsDocCompletionProvider(client),
+			new JsDocCompletionProvider(client, fileConfigurationManager),
 			'*');
 	});
 }
diff --git a/extensions/typescript-language-features/src/languageProvider.ts b/extensions/typescript-language-features/src/languageProvider.ts
index 5634edb44df..2cb36eb948b 100644
--- a/extensions/typescript-language-features/src/languageProvider.ts
+++ b/extensions/typescript-language-features/src/languageProvider.ts
@@ -72,7 +72,7 @@ export default class LanguageProvider extends Disposable {
 			import('./languageFeatures/formatting').then(provider => this._register(provider.register(selector, this.description.id, this.client, this.fileConfigurationManager))),
 			import('./languageFeatures/hover').then(provider => this._register(provider.register(selector, this.client))),
 			import('./languageFeatures/implementations').then(provider => this._register(provider.register(selector, this.client))),
-			import('./languageFeatures/jsDocCompletions').then(provider => this._register(provider.register(selector, this.description.id, this.client))),
+			import('./languageFeatures/jsDocCompletions').then(provider => this._register(provider.register(selector, this.description.id, this.client, this.fileConfigurationManager))),
 			import('./languageFeatures/organizeImports').then(provider => this._register(provider.register(selector, this.client, this.commandManager, this.fileConfigurationManager, this.telemetryReporter))),
 			import('./languageFeatures/quickFix').then(provider => this._register(provider.register(selector, this.client, this.fileConfigurationManager, this.commandManager, this.client.diagnosticsManager, this.telemetryReporter))),
 			import('./languageFeatures/refactor').then(provider => this._register(provider.register(selector, this.client, this.fileConfigurationManager, this.commandManager, this.telemetryReporter))),