Hi, thanks guys. Yes @Rick BrewsterI did scroll down and choose the file type not type it in manually. I think you are right @Djisves I think it is a setting where I've accidentally made paint.net the default to open all file types. What was confounding me is that I always save a paint.net version with the layers separate and then a PNG or JPEG version which is flattened. It was frustrating me because I couldn't tell which was which because they both say they are PDN files when I hover over the thumbnail in the destination folder but one is actually a PNG so I'm just guessing which to try to upload It's probably a setting I've got wrong. I'll keep trying to figure it out. Thanks for the help.