I have never sent a huge file, but you should always hear the success tones at the end. I had this same kind of problem when I was sending RTF or HTML files and didn't think it was working. I wish I had a large file and a big card that was not full to transfer the file. What I do, I go to the folder the file is in and hit enter on the file. It is the easiest way. You can also highlight a whole folder of MP3 files, but then they don't always get transferred in the correct order. I think the CD/MP3 player somehow puts them in the correct order sometimes. I don't think you should have a problem with files that are too large, although the limit for text files is apparently about 4.5 MB. By the way, have you sent the files as music files in one of those check boxes? I don't understand it either, Some of those keys should certainly do something. Kurt