diff --git a/src/filesystem/__tests__/path-utils.test.ts b/src/filesystem/__tests__/path-utils.test.ts
index 868d8f08af..5530cba1c3 100644
--- a/src/filesystem/__tests__/path-utils.test.ts
+++ b/src/filesystem/__tests__/path-utils.test.ts
@@ -70,6 +70,12 @@ describe('Path Utilities', () => {
         .toBe('/home/user/some path');
       expect(normalizePath('"/usr/local/some app/"'))
         .toBe('/usr/local/some app');
+      expect(normalizePath('/usr/local//bin/app///'))
+        .toBe('/usr/local/bin/app');
+      expect(normalizePath('/'))
+        .toBe('/');
+      expect(normalizePath('///'))
+        .toBe('/');
     });
 
     it('removes surrounding quotes', () => {
diff --git a/src/filesystem/path-utils.ts b/src/filesystem/path-utils.ts
index c897b9d2c7..50910b995b 100644
--- a/src/filesystem/path-utils.ts
+++ b/src/filesystem/path-utils.ts
@@ -55,7 +55,7 @@ export function normalizePath(p: string): string {
   if (isUnixPath) {
     // For Unix paths, just normalize without converting to Windows format
     // Replace double slashes with single slashes and remove trailing slashes
-    return p.replace(/\/+/g, '/').replace(/\/+$/, '');
+    return p.replace(/\/+/g, '/').replace(/(?<!^)\/$/, '');
   }
 
   // Convert Unix-style Windows paths (/c/, /d/) to Windows format if on Windows