Originally Posted by Mikerman
SanDisk has noted that aac rips done by certain rippers (Nero for one, if I recall correctly? others, please correct this if wrong) can cause compatibility problems. (Sigh!) But I thought that iTunes was ok in that regard. Also, it seems that super high aac rip rates, like 320kbps, also can cause issues (it's almost as if there is too much information there for the Clip Zip to handle), but you seem fine there as well.
By any chance, do you have high data album art associated with the files (over 100KB)? That likewise can cause an issue, it seems.
Thanks for the reply! How do you check the size of the album art? I'm not sure about my ripped AACs, as I think a lot of them had no art, but my purchased ones have it for sure, and I assume they came with the file by default. I know iTunes searches for album art when you add files to it, but I'm not sure if it embeds them, as the iTunes music folder has its own album art folder, so I guess that it's a library thing for ripped albums without embedded art. The purchased AACs are the 256kbps non-DRM variety, unlike my ripped ones.