The Toolbar delete button is enabled only if the selected item's parent folder can be deleted, even if the file itself has delete permission. Steps to reproduce: 1. Openthe following demo, the delete permissions ase given to the root "images" folder (DeletePaths="~/FileExplorer/Examples/Overview/images") http://demos.telerik.com/aspnet-ajax/fileexplorer/examples/overview/defaultcs.aspx 2. Open the root folder from the tree (images) 3. Select an item from the grid Actual: The Delete button is not enabled Expected: The delete button is enabled, as the images folder is granted with delete permissions WORKAROUND: <telerik:RadFileExplorer ID="RadFileExplorer1" runat="server" EnableCopy="True" EnableOpenFile="True" OnClientLoad="explorerLoad" Height="500px" Skin="Default" Configuration-MaxUploadFileSize="900000000"> <Configuration ViewPaths="~/Images_2" DeletePaths="~/Images_2" UploadPaths="~/Images_2" /> </telerik:RadFileExplorer> <script> function explorerLoad(fileExplorer, args) { fileExplorer._fileList.add_itemSelect(Function.createDelegate(fileExplorer, function (fileList, args) { fileExplorer._updateToolbar(null, null, args.get_item().get_permissions()); fileExplorer.raise_itemSelected(args.get_item()); })); } </script>