I import audiobook CDs into iTunes and join all tracks into a single MP3 per CD. I numbered and dragged the files in a playlist onto the clip and the files would play in order. After the last firmware upgrade, it took me a while to figure out that the new Clip firmware is first sorting the order of the files according to the *number of tracks in each file*. The workaround in iTunes is to set the number of tracks to 1 and the Album name to the same thing and order the disk names as before. For example, Name: Lord Jim 1, Tracks 1 of 1, Album: Lord Jim, next Name: Lord Jim 2, Tracks 1 of 1, Album: Lord Jim, etc I hope this helps. I use a Mac.