Does this problem affect sending other kinds of files to Incredimail, or is the problem ONLY with photos? Could you check the file extension? To view file extensions, please try the steps in this article: https://www.bleepingcomputer.com/tutorials/how-to-show-file-extensions-in-windows/ If the file does not have a common image file extension such as .jpg or .png or .gif then Windows may not know how to "send" it. If the file does not show ANY extension, it could be a web shortcut. You an right-click the photo, click Properties, and then it should indicate whether it's a normal photo or a shortcut to the web address of the photo.