I am trying to add a RadComboBox to the RadUploadItem so that I can have the user select a value for each file before uploading them. I have already copied the template and edited it and the combobox shows up fine, but if I click the Add More Files button and select additional files, the selected values in the comboboxes for the previously-selected files are lost (reset to nothing selected). My problem seems similar to the one posted here: http://www.telerik.com/community/forums/silverlight/upload/add-more-files-functionality-and-custom-parameters.aspx Back on 1/14/2010, it was stated that when the Add More Files is used, the item containers for all files are re-created, so this functionality should not be used [if you want to customize the item]. I'm hoping that this has since been fixed and that I am just missing something.