I received this question from listener Ted:
Have you ever tried using the Autofill method of transferring content to your iPod Shuffle? I have found that these files are ignored. If you drop the file directly onto the iPod Shuffle icon (in iTunes) or drop a playlist containing these (.mp4b) onto the icon, everything works as expected. However if you were to specify the same playlist (containing 1 or more bookmarkable aac files) in the “Autofill” dropdown, these files are skipped when you “autofill.” At least for me.
Have any of you experienced this? Does anyone know why this might be happening?