diff --git a/src/vs/code/node/cli.ts b/src/vs/code/node/cli.ts
index 0207af243dc..bd7acdf794c 100644
--- a/src/vs/code/node/cli.ts
+++ b/src/vs/code/node/cli.ts
@@ -59,7 +59,11 @@ export async function main(argv: string[]): Promise<any> {
 			if (process.env['VSCODE_DEV']) {
 				tunnelProcess = spawn('cargo', ['run', '--', 'tunnel', ...argv.slice(5)], { cwd: join(getAppRoot(), 'cli') });
 			} else {
-				const tunnelCommand = join(dirname(process.execPath), 'bin', `${product.tunnelApplicationName}${isWindows ? '.exe' : ''}`);
+				const appPath = process.platform === 'darwin'
+					// ./Contents/MacOS/Electron => ./Contents/Resources/app/bin/code-tunnel-insiders
+					? join(dirname(dirname(process.execPath)), 'Resources', 'app')
+					: dirname(process.execPath);
+				const tunnelCommand = join(appPath, 'bin', `${product.tunnelApplicationName}${isWindows ? '.exe' : ''}`);
 				const tunnelArgs = argv.slice(3);
 				tunnelProcess = spawn(tunnelCommand, ['tunnel', ...tunnelArgs]);
 			}