I'm trying to figure out why a group of songs just will not sync to my iPod Shuffle (1st gen). The only connection I could find between these few songs is that they were all converted from FLAC to AAC using Toast. Is Toast making incompatible AAC files? However, I swear some other songs I also converted using Toast DID sync to my iPod... in fact I know this to be the case. I always use the same settings in Toast, so why would only some of them not sync? The files are linked properly in the Library iTunes plays them fine. They're not un-checked. They don't have any weird characters in the file names. I just don't know.