diff --git a/extensions/typescript-language-features/src/languageFeatures/languageConfiguration.ts b/extensions/typescript-language-features/src/languageFeatures/languageConfiguration.ts
index ccd59d51773..75d32770a68 100644
--- a/extensions/typescript-language-features/src/languageFeatures/languageConfiguration.ts
+++ b/extensions/typescript-language-features/src/languageFeatures/languageConfiguration.ts
@@ -15,7 +15,9 @@ import * as languageModeIds from '../utils/languageModeIds';
 const jsTsLanguageConfiguration: vscode.LanguageConfiguration = {
 	indentationRules: {
 		decreaseIndentPattern: /^((?!.*?\/\*).*\*\/)?\s*[\}\]].*$/,
-		increaseIndentPattern: /^((?!\/\/).)*(\{[^}"'`]*|\([^)"'`]*|\[[^\]"'`]*)$/
+		increaseIndentPattern: /^((?!\/\/).)*(\{[^}"'`]*|\([^)"'`]*|\[[^\]"'`]*)$/,
+		// e.g.  * ...| or */| or *-----*/|
+		unIndentedLinePattern: /^(\t|[ ])*[ ]\*[^/]*\*\/\s*$|^(\t|[ ])*[ ]\*\/\s*$|^(\t|[ ])*[ ]\*([ ]([^\*]|\*(?!\/))*)?$/
 	},
 	wordPattern: /(-?\d*\.\d\w*)|([^\`\~\!\@\%\^\&\*\(\)\-\=\+\[\{\]\}\\\|\;\:\'\"\,\.\<\>\/\?\s]+)/g,
 	onEnterRules: [
diff --git a/extensions/typescript-language-features/src/test/unit/onEnter.test.ts b/extensions/typescript-language-features/src/test/unit/onEnter.test.ts
index 0aeb8425b0a..cd0d99c0e41 100644
--- a/extensions/typescript-language-features/src/test/unit/onEnter.test.ts
+++ b/extensions/typescript-language-features/src/test/unit/onEnter.test.ts
@@ -67,4 +67,47 @@ suite.skip('OnEnter', () => {
 					`    x`));
 		});
 	});
+
+	test('should not indent after a multi-line comment block 1', () => {
+		return withRandomFileEditor(`/*-----\n * line 1\n * line 2\n *-----*/\n${CURSOR}`, 'js', async (_editor, document) => {
+			await type(document, '\nx');
+			assert.strictEqual(
+				document.getText(),
+				joinLines(
+					`/*-----`,
+					` * line 1`,
+					` * line 2`,
+					` *-----*/`,
+					``,
+					`x`));
+		});
+	});
+
+	test('should not indent after a multi-line comment block 2', () => {
+		return withRandomFileEditor(`/*-----\n * line 1\n * line 2\n */\n${CURSOR}`, 'js', async (_editor, document) => {
+			await type(document, '\nx');
+			assert.strictEqual(
+				document.getText(),
+				joinLines(
+					`/*-----`,
+					` * line 1`,
+					` * line 2`,
+					` */`,
+					``,
+					`x`));
+		});
+	});
+
+	test('should indent within a multi-line comment block', () => {
+		return withRandomFileEditor(`/*-----\n * line 1\n * line 2${CURSOR}`, 'js', async (_editor, document) => {
+			await type(document, '\nx');
+			assert.strictEqual(
+				document.getText(),
+				joinLines(
+					`/*-----`,
+					` * line 1`,
+					` * line 2`,
+					` * x`));
+		});
+	});
 });