When uploading Images users can make the mistake of uploading them as Files so that they are not treated as Images by the system. Images uploaded as Files aren’t select-able in Rich Text Editors or other areas of the product that expect Image Assets. The images then have to be deleted and recreated.
Enhance the File Widget and the Bulk Upload Gadget to detect the type of File being uploaded and if it is an image (based on the extension) - create an Image Asset instead of a File Asset.