At present, when an invalid file is selected, the alert message does not clearly indicate what is the validation error - invalid extension or the size being too large. It should show a message that clearly states what the problem is so the user can fix it. For the time being you can handle the AsyncUpload's OnClientValidationFailed event and show different messages—http://docs.telerik.com/devtools/aspnet-ajax/controls/asyncupload/client-side-programming/onclientvalidationfailed. Example: ASP.NET ------------------------------- <telerik:RadFileExplorer runat="server" ID="RadFileExplorer1"> <Configuration ViewPaths="~/" UploadPaths="~/" DeletePaths="~/" SearchPatterns="*.jpg" /> </telerik:RadFileExplorer> <script> // Prevent the built-in validation alert Telerik.Web.UI.RadFileExplorer.prototype._showUploadValidationFailedAlert = function () { } function OnClientValidationFailed(sender, args) { var fileExtention = args.get_fileName().substring(args.get_fileName().lastIndexOf('.') + 1, args.get_fileName().length); if (args.get_fileName().lastIndexOf('.') != -1) {//this checks if the extension is correct if (sender.get_allowedFileExtensions().indexOf(fileExtention) == -1) { alert("Wrong Extension!"); } else { alert("Wrong file size!"); } } else { alert("not correct extension!"); } } </script> ------------------------------- C# ------------------------------- RadFileExplorer1.AsyncUpload.OnClientValidationFailed = "OnClientValidationFailed"; ------------------------------- VB ------------------------------- RadFileExplorer1.AsyncUpload.OnClientValidationFailed = "OnClientValidationFailed" -------------------------------