diff --git a/extensions/typescript-basics/language-configuration.json b/extensions/typescript-basics/language-configuration.json
index 6676b50677e..8ba8fb0b860 100644
--- a/extensions/typescript-basics/language-configuration.json
+++ b/extensions/typescript-basics/language-configuration.json
@@ -218,6 +218,33 @@
 			"action": {
 				"indent": "outdent"
 			}
-		}
+		},
+		// Indent when pressing enter from inside ()
+		{
+			"beforeText": "^.*\\([^\\)]*$",
+			"afterText": "^[^\\(]*\\).*$",
+			"action": {
+				"indent": "indentOutdent",
+				"appendText": "\t",
+			}
+		},
+		// Indent when pressing enter from inside {}
+		{
+			"beforeText": "^.*\\{[^\\}]*$",
+			"afterText": "^[^\\{]*\\}.*$",
+			"action": {
+				"indent": "indentOutdent",
+				"appendText": "\t",
+			}
+		},
+		// Indent when pressing enter from inside []
+		{
+			"beforeText": "^.*\\[[^\\]]*$",
+			"afterText": "^[^\\[]*\\].*$",
+			"action": {
+				"indent": "indentOutdent",
+				"appendText": "\t",
+			}
+		},
 	]
 }
diff --git a/src/vs/editor/contrib/indentation/test/browser/indentation.test.ts b/src/vs/editor/contrib/indentation/test/browser/indentation.test.ts
index 793c4c33681..92423c46a70 100644
--- a/src/vs/editor/contrib/indentation/test/browser/indentation.test.ts
+++ b/src/vs/editor/contrib/indentation/test/browser/indentation.test.ts
@@ -838,7 +838,7 @@ suite('`Full` Auto Indent On Type - TypeScript/JavaScript', () => {
 		});
 	});
 
-	test.skip('issue #43244: indent when lambda arrow function is detected, outdent when end is reached', () => {
+	test('issue #43244: indent when lambda arrow function is detected, outdent when end is reached', () => {
 
 		// https://github.com/microsoft/vscode/issues/43244