diff --git a/src/cjs/api/module-resolve-filename/resolve-implicit-extensions.ts b/src/cjs/api/module-resolve-filename/resolve-implicit-extensions.ts
index 8b9b20fdd..48cd7540e 100644
--- a/src/cjs/api/module-resolve-filename/resolve-implicit-extensions.ts
+++ b/src/cjs/api/module-resolve-filename/resolve-implicit-extensions.ts
@@ -15,7 +15,7 @@ export const createImplicitResolver = (
 ): SimpleResolve => (
 	request,
 ) => {
-	if (request === '.' || request === '..') {
+	if (request === '.' || request === '..' || request.endsWith('/..')) {
 		request += '/';
 	}
 
diff --git a/src/esm/hook/resolve.ts b/src/esm/hook/resolve.ts
index 67ef263a3..0702ea8e2 100644
--- a/src/esm/hook/resolve.ts
+++ b/src/esm/hook/resolve.ts
@@ -141,7 +141,7 @@ const resolveDirectory: ResolveHook = async (
 	context,
 	nextResolve,
 ) => {
-	if (specifier === '.' || specifier === '..') {
+	if (specifier === '.' || specifier === '..' || specifier.endsWith('/..')) {
 		specifier += '/';
 	}
 
diff --git a/tests/fixtures.ts b/tests/fixtures.ts
index f76f413fc..cb048267f 100644
--- a/tests/fixtures.ts
+++ b/tests/fixtures.ts
@@ -212,7 +212,10 @@ export const files = {
 		`,
 
 		'period.in.name.ts': 'export { a } from "."',
-		'dotdot/index.ts': 'export { a } from ".."',
+		dotdot: {
+			'index.ts': 'export { a } from ".."',
+			'dotdot/index.ts': 'export { a } from "../.."',
+		},
 
 		'index.js': 'throw new Error("should not be loaded")',
 	},
diff --git a/tests/specs/smoke.ts b/tests/specs/smoke.ts
index 0bd1fd9d7..4d437cfae 100644
--- a/tests/specs/smoke.ts
+++ b/tests/specs/smoke.ts
@@ -284,6 +284,7 @@ export default testSuite(async ({ describe }, { tsx, supports, version }: NodeAp
 						import './ts/period.in.name';
 						import '@/ts/period.in.name';
 						import './ts/dotdot';
+						import './ts/dotdot/dotdot';
 
 						// .jsx
 						import * as jsx from './jsx/index.jsx';