One of the easiest ways to squeeze in a good book during a vacation or commute is by listening to audio books on your iPod or iPhone. Audio books can be downloaded online using services such as iTunes or Audible, but sometimes it's cheaper to get your books on CD and rip them manually.
But if you've ever tried to transfer a multi-CD audio book onto an iPod, you've probably run into problems such as chapters playing out of order, mislabelled or missing files, or just a generally messy experience. There's about a dozen ways that something as seemingly simple as ripping an audio book CD to your iPod can go wrong, but there's certainly a few tips and tricks that can make the experience smoother.
In this slideshow we'll show you the best way we've found for getting audio book CDs into iTunes and onto the iPod.

First, put the CD into your computer and launch iTunes. If iTunes automatically prompts you asking if you'd like to import the CD, say no — there's a few things we'll want to do before allowing iTunes to import the CD.
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Hopefully, you'll see all the correct information associated with the track, title and artist info — but audio books are notorious for having bad or inconsistent data. We can fix any missing information later.
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Now, open up your iTunes preferences and under import settings, select AAC and from the drop-down settings menu, select Spoken Podcast. This is technically a low quality setting, but it's been optimised specifically for voice, so you'll never hear the difference. The reason we're changing it is that if you're dealing with a six- to 10-CD audio book, this will significantly cut down the time it takes to encode each CD. Still, don't forget to change it back to your original setting once you're finished, or the next music CD you rip could sound funky.
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After hitting OK. Select your audio book CD from the left column. Now, if you were playing this CD on a CD player, it would make sense to have each chapter broken up into these three- to five-minute tracks, so you could easily skip forward and backward to find your place. But the beauty of playing audio books on an iPod is that it automatically resumes playback where you last left off. In fact, having a six-CD audio book broken up into hundreds of files on your iPod is just a recipe for trouble. So, we're going to show you how to rip each CD as a single file.
Hold down the shift key and select the first and last track of the CD. This should highlight all the tracks. You could do the same thing by selecting the first track, going to the Edit menu and using Select all.
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With all the tracks of your CD selected, go into the advanced menu and select Join CD Tracks. You'll notice that the tracks of your CD shift to the right slightly and have a line on the left that connects them all together.
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Now, hit the import CD button in the bottom right corner. iTunes is now ripping the CD to your computer as a single file. Eject the CD and do the same process for the remaining CDs in your collection: put in the CD, select all the tracks, tell iTunes to join the tracks and then hit import.
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Once all the CDs have been imported, the easiest way to find them is by clicking on the Recently Added playlist built into iTunes. The files should be right at the top.
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Now, let's make sure the files all have the correct information and playback on your iPod in the correct order. Select all the tracks you just ripped and select Get Info from the file menu or by right-clicking with your mouse. In the info pane, you should see Artist and Album info, which serves as Author and Title. If it's not there, plug it in.
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You'll also see track number and disc number info. You'll have to enter this info on a track-by-track basis, but it's worth it to make sure the book plays each disc in the correct order. Just be thankful you're doing this with six-to-10 tracks instead of hundreds. If you find out later that your iPod is playing chapters out of order, this is the setting to go back and tweak.
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Now, go to the Options section and make sure that Media Kind is designated as Audiobook, the "Remember Position" setting is set to Yes, "Part of a Compilation" is set to No, and "Skip When Shuffling" is set to Yes. Changing these settings will group the files correctly in the iTunes audio book directory, ensure that playback is automatically bookmarked and prevent a chapter of "Crime and Punishment" from popping up in a party shuffle.
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Finally, to get the audio book onto your iPod, connect your iPod to the computer. If your iPod is set up to transfer content automatically (its default setting), the new audio book content should sync right over. For users who've configured their iPod for manual file management, simply drag and drop the book from the Audiobook section of iTunes and onto the iPod icon.
On most iPods, audio books are found in a separate directory within the music menu. On the iPhone or iPod Touch, you can find audio books in the "More" section of the iPod menu.
(Credit: Donald Bell/CBS Interactive)