Q: When I try to sync my audio books to my new 160GB iPod classic it puts all chapters together by number (e.g. chapter 1, then chapter 2, etc) and makes the books unplayable. It seems to break them and catogizes them by chapter number not titles. How can I fix this?
A: How audiobooks are organized on the iPod depends on a number of factors, and you should ensure that tags such as album and artist are filled out appropriately to identify the author (artist) and book title (album) name for each chapter.
You should also ensure that your audiobooks are properly tagged with a “Media Kind” of “Audiobook.” This can be set by selecting the tracks, choosing Get Info from the iTunes File menu and selecting the Options tab.
You may also find it better to combine any multi-chapter audiobooks into a single audiobook file rather than using separate chapters. Audiobooks in iTunes and on the iPod support chapter markers and can remember your playback position. This is generally easier than trying to manage playlists of multiple chapters. If you’re importing your audiobooks from CD, you can use the “Join CD Tracks” option found on the Advanced menu to merge multiple CD tracks into a single MP3 or AAC file.
There are also third-party tools available for both Mac and Windows that can be used to merge multiple audiobook chapters into a single file and insert the necessary chapter markers. For more information, be sure to check out our Guide to iTunes Audiobooks, Podcasts + iTunes U.