Hi Todd Davis,
Yes - you can edit the template of the RadUploadItem and to add textboxes for each item. Then you should get the text that was written in each textbox and pass it to the upload handler. In the upload handler you can process it in the way you want - e.g. add to DB, store in separate file, etc..
To pass the textbox data to the upload handler please check this help article:
Please let us know if you need more help on that.
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