How to rip an audiobook to iTunes so it has bookmarks

RecallI won’t debate the ethics of ripping and sharing CDs in this post. Suffice it to say that folks who know me know my stand on this issue.

Where I can get audiobooks already in MP3 format I just do that. It saves a LOT of hassle. I even will get them in DRM’d format as I don’t tend to listen to audiobooks more than once.

But there is still a lot of content out there that you can get only on CD that I want to listen to on my iPod (I don’t have a CD player in my car, nor do I intend to get one), so I consider it fair use to purchase the CD and rip it for my own use on my iPod.


  • I tend to listen to lengthy audiobooks (ones that I really wouldn’t have the time to read) so they often have many CDs. In iTunes I go to Edit > Preferences…  then click on the “Advanced” tab and then on the importing sub-tab I temporarily set:
  • “On CD Insert” = “Import CD and Eject”,
  • “Import using” = “AAC Encoder”,
  • “Setting” = “High Quality (128 kbps)”  <– personal preference, you can set for “Spoken Podcast” but I like the higher sound quality better.
  • Start putting your CDs in and, with luck, you’ll be offered albums from CDDB that will label your tracks for you. When  there is a conflict (sometimes different CD tracks are uploaded for the same CDs – usually by folks with differing ideas about how the tracks should be labeled), you’ll be offered a choice of available albums. You aren’t given anything more than the album name (no track details) at this stage, so pick one and make sure that you pick the same “style” from now on so that all your tracks will be labeled consistently. I’ll post a subsequent article about how to correct an incorrect choice in a few days.
  • Once you’ve pulled in all of your CDs fire up xnview (a free graphic and photoviewer) and navigate to where your tracks are located. If you don’t know where this is, right-click on the track in iTunes and choose “Show in Windows Explorer” (sorry Mac users). You may find that your tracks have been stored in more than one folder depending on the naming that you got from CDDB. In xnview, select all of the *.m4a files (aac encoded) and right click to select “Rename…”.
  • You’ll be presented with a dialog titled “Batch Rename” (as of xnview version 1.91.6). In the upper right corner check the “Extension” box and type “m4b”. You’ll see all the files you selected with the old name and the proposed new names showing at the bottom of this dialog. Click “Rename”.
  • Back in iTunes, select all of the tracks that you’ve just renamed and delete them (you’ll see little exclamation points appearing beside them as iTunes figures out that it can no longer find the files).
  • Then select File > Add Folder to Library… and choose the folders with the renamed files in them.
  • For ease of listening I create a smart playlist for these audiobooks:
  • I usually use the “Album Name contains” and use some significant part of the audiobook name
  • I also specify that the play count < 1
  • Make sure you sort by the track name. If you end up with a bad sorting order (sometimes happens with > 9 chapters), consider making two smart playlists and then use the Rating to separate them – one star rating for the first 9 chapters, none for the rest and then add this as a criteria for the smarplaylist.

Then, when I’m driving (my most frequent listening venue) all I need to do after I’ve selected the playlist and listened to the playlist starting from the beginning. If, in “settings” on the iPod, I have “Shuffle” set to “songs” then my iPod will stop after each track (my preferred method). I hit the middle button 4 times and I get the next track (the “count” parameter above excludes the one(s) I’ve already listened to). If I have “Shuffle” set to “none” then the iPod will play each track in sequence.  This is different between my older generation iPod (which does not refresh the list dynamically) and my current one (iPod Video – 30 GB) so YMMV.

Hopefully you find this useful.

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