diff --git a/src/puter-js/src/modules/FileSystem/operations/upload.js b/src/puter-js/src/modules/FileSystem/operations/upload.js
index ea2dcbad..8ca19c6d 100644
--- a/src/puter-js/src/modules/FileSystem/operations/upload.js
+++ b/src/puter-js/src/modules/FileSystem/operations/upload.js
@@ -206,7 +206,7 @@ const upload = async function(items, dirPath, options = {}){
         // Generate the requests to create all the 
         // folders in this upload
         //-------------------------------------------------
-        dirs.sort();
+        dirs.sort((a, b) => b.path.length - a.path.length);
         let mkdir_requests = [];
     
         for(let i=0; i < dirs.length; i++){