Frequently Asked Questions About Audiobooks, iTunes, and iPods

My instructions for importing audiobooks from different CD formats into iTunes have inspired a lot of follow-up questions. To help keep things organized, I’ve moved them and my answers from the comments where they originated to this FAQ.

I love questions, so please feel free to send them to me at the email address in the sidebar. I generally respond in a couple days, and try to publish them here as well as reply via email. More questions means more answers, and a better experience for everyone.

Frequently asked questions about importing audiobooks into iTunes

Click on a question to scroll down to the answer.

How do I get my audiobook to appear in the Audiobooks menu on my iPod?

Note: If you upgrade to iTunes 8, this answer becomes incredibly easy, and you can skip all of the crazy instructions below. If you’re not yet using iTunes 8, reading the below will surely convince you to upgrade.

This is part of what I mean when I wrote about the “full” level of being an audiobook in iTunes and Audiobooks. For whatever reason, Apple has decided — in both iTunes and on the iPod — that a true audiobook must be in either Audible.com’s .aa format or in Apple’s .m4b Protected AAC format. Anything else, and it won’t show up in the Audiobooks menu.

So, to get your audiobooks to show up there, you need to trick iTunes and your iPod into thinking the tracks are stored in that format. On Windows, this is easy enough to explain and understand, but the process is labor-intensive. You need to change the file extension for every track in the audiobook from .m4a to .m4b, and then play a few seconds of each track after renaming.

Mac OS X users are more fortunate. While the process of changing the apparent format is more tricky, the Make Bookmarkable script at Doug’s ApplesScripts for iTunes makes the whole process as simple as selecting the tracks of your imported audiobook and choosing Make Bookmarkable from the Scripts menu of iTunes (it’s the stylized “S” icon between the Window and Help menus). This script was recently updated, and now seems to handle all known issues for audiobooks. Download the script for installation and usage instructions. Note that you may still need to play a few seconds of each track, to force iTunes to recognize the changed state of the files.

How do I get my audiobook to appear in the LIBRARY > Audiobooks source list in iTunes 7?

The Audiobooks source list in the iTunes 7 LIBRARY source group appears to use the same criteria for what is an audiobook as the iPod. So, tracks which are in Audible.com’s .aa format or in Apple’s .m4b Protected AAC format should appear in the Audiobooks source list, as long as their bit rate is 64 kbps or lower. (Bit rates higher than 64 kbps don’t make sense for audiobooks, it doesn’t improve their quality noticeably.)

The easiest way to change the format is explained in the prior answer.

I imported two books on CD following your instructions. One shows up in the Audiobooks menu on my iPod, the other does not. How come?

Most likely, you changed the file extensions for one book, but not the other. iPods will only put tracks which are .aa (Audible.com only) or .m4b in the Audiobooks menu.

You should still be able to find the other book on your iPod, by going to Music > Genres > Audiobook (assuming you changed the genre of your CD files to “Audiobook” as outlined above). A couple more clicks, but the book is probably there.

Last thought: After converting some audiobook tracks to Protected AAC (.m4b) format, iTunes may still think they are standard AAC format (.m4a), and when syncing to an iPod, they’ll still not show up in the Audiobooks menu. I’ve found that playing the first few seconds of each track in iTunes will force iTunes to recognize the “real” format of the file, changing it to Protected AAC. Then a sync to the iPod will produce the desired results, displaying the book files in the Audiobooks menu.

I tried all of your suggestions, and my audiobooks still won’t show up in the Audiobooks menu. Is there anything else I can do?

Sometimes, no matter what you do, iTunes remains convinced that the tracks should not be in the Audiobooks menu. When this happens, those tracks are doomed, there is nothing you can do with them directly. Here’s the very last thing you can try:

  1. Select one of the tracks in the iTunes Library, and choose Show Song File from the File menu. This should display all of the tracks in the audiobook in your file manager of choice (Finder on Mac OS X, Windows Explorer on Windows).
  2. Select all of the audiobook’s tracks, and copy them to your Desktop.
  3. Switch back to iTunes, select all of the audiobook’s tracks, and delete them. When asked, make sure you really delete them and move the files to the Trash or Recycle Bin.
  4. Quit iTunes. Restart iTunes.
  5. Drag the copied version of the audiobook into the iTunes Library.

This version should now appear in the Audiobooks menu. If not, you have to give up, or start completely over.

Is there a way to sort or group the audiobook tracks in the Audiobooks menu on my iPod? Like, say, by author, or by book, instead of listing every single individual book track?

The short answer is, unfortunately, no. The Audiobooks menu is listed strictly by track name, which means you can end up with quite a few items listed which look identical, because they are for the same book, with the only difference being a “xx of yy” at the end of the track name.

However, you can access your audiobooks via the Genres > Audiobooks menu instead. There you will find your books grouped by author, and under author grouped by book title. It’s a few too many scroll-and-clicks for my taste, but it beats trying to find the seventh track of a book with a long title by counting down the list in Audiobooks because the long title pushes the track numbers off-screen on your iPod mini. Which happens to me quite often…

When I play back the discs on my iPod, they are playing in a random order. How do I make the book play in the right order?

Here are three things to try:

  1. Make sure that Shuffle Mode is turned off: Settings > Shuffle > Off.
  2. Make sure you’ve named the tracks in such a way that sorting them in name order is the right order, e.g., “Kill the Messenger 01”, “Kill the Messenger 02”, etc.
  3. Make sure you’ve put the right track number and disc number information onto all the tracks. I leave the track numbers blank, and use the disc number only. It should be numbered sequentially, just like in the file names, except you don’t need leading zeros. This is frequently the problem; the straight importing procedure can leave semi-random information in the track fields if you are not careful to clear it out.

As a last resort, you can create a new Playlist in iTunes, and manually add and order all of the tracks for the book. Then you will need to access the book via the Music > Playlists menu, but the tracks should appear in the right order.

Why do I need to convert tracks to Protected AAC? Why do I need to make the tracks bookmarkable?

From what I’ve read and experienced, only two types of files are truly bookmarkable: Audible.com’s proprietary format, which iTunes can play, but not create; and AAC files which iTunes and iPods believe are in the .m4b Protected AAC format. MP3 files can be made bookmarkable, but do not show up in the Audiobooks section of an iPod, so I’ve stayed away.

Note that an iPod will normally hold your place on a given track, even across off/on cycles, but this is not the same as being bookmarkable, because it will lose that place on a track the moment you play a different track. This is probably fine behavior when you’re listening to music; you can just play something else. But it doesn’t work so well for the linear narrative structure of most books. So being bookmarkable is very beneficial if you use your iPod for audiobooks (and podcasts, but that’s another subject).

Doug Adams wrote The Fabulous Bookmarkable Matrix to help explain which kinds of files are bookmarkable, and which will show up in the Audiobooks section of which iPod. Doug’s AppleScripts are an outstanding resource, so check out the whole site!

Isn’t the AAC format a proprietary Apple audio format? Isn’t it less compatible with audioplayers?

The instructions I provide on this site import audiobooks into AAC format, an industry standard format. You can get more information from Apple’s AAC page or Wikipedia’s more detailed entry. There are a number of ways in which it is better than the MP3 format, but because it is a newer standard, it may be unsupported on older devices. But as an open standard, anyone can support it, and many do. Details at those links.

An important distiction to make is in regards to the Protected AAC format, which is an AAC format track wrapped in Apple’s FairPlay DRM system. These tracks are indeed not compatible with players besides the iPod and iTunes, and other Apple devices. But this is because of the DRM, not because of AAC.

Why is the Join CD Tracks menu item dimmed in the Advanced menu?

There are two reasons why this command might be dimmed. The first is that you’ve got something besides CD tracks selected, i.e., even one track which is already in your library. For whatever reason, iTunes can only join tracks before they are imported from a CD, so anything besides what’s on the CD will cause the menu command to be dimmed.

The second reason why this menu item might be dimmed is much more subtle. The track list of the CD must be sorted by the track number column (which isn’t labeled). If it’s sorted by any other column, the menu command will be dimmed. The track number column is the left-most column of the songs list, as displayed here:

iTunes Track Number Column

The Apple knowledgebase article iTunes: Join CD Tracks Command Is Dimmed has additional details on this behavior.

Is it possible to join the tracks of already existing albums or is that done as part of the recording process?

See the post How to join multiple tracks into a single audiobook file for the answer to this question.

The “Make Bookmarkable” script is nice for Mac users, but how do I do this in Windows?

If you’re using iTunes on Windows, there is no equivalent to AppleScript; you’ll need to do this manually. Changing the filename extensions from .m4a to .m4b will do the trick. Use the File/Show Song File menu choice to reveal the folder with the book files, and rename away.

How do I change the file extension in Windows? I can’t even see the file extensions!

If you can’t see the .m4a file extension, then uncheck the Hide extensions for known file types option in the Advanced Settings section of the Folder Options control panel:

Windows XP Folder Options Advanced Settings

I use Windows and I’m importing a lot of books. Renaming all those files seems like a pain in the butt! Is there any way to automate it?

If you are comfortable using a command shell in Windows, you can simply type the following, once you have changed directories to the folder containing the files to be renamed:

ren *.m4a *.m4b

If you’re not afraid of trying new software, a reader recommended the tool Extension Changer, which from the description and screenshots looks like it might be a great solution for automating the conversion. I can’t recommend it from personal use, but you might give it a look.

When I rename the files as described, iTunes loses them! How do I fix this, or make it not happen?

This is a problem only on Windows. It is due to Windows not “keeping track” of the file through the file name change. Because the file name changed, and since the renaming happened “outside” it, iTunes doesn’t know where the file moved to. You will need to “reattach” the files, by right-clicking and viewing their info; iTunes will give you the opportunity to find the lost files. Pain in the butt, but I don’t know of a way around it on Windows…

Will these instructions work with an iPod shuffle?

I don’t think the iPod shuffle is well-suited to audiobook playback. It is not impossible, but it is certainly painful (Rochelle tried it for a couple weeks after her old iPod died on a trip). If you are not dissuaded, read more details in the article Which iPod Should I Buy?.

I use iTunes, but I don’t have an iPod, I have a different player. Will these instructions work for me?

If you change your import settings to use the MP3 format instead of the AAC format, you can probably get the files to work on almost any brand of digital audio player, even older ones. But since iTunes only synchronizes (gracefully) with iPods, you’ll have to figure out how to transfer the files to your player on your own.

But I can say, from personal experience with another digital audio player, that other players do not work nearly as well as an iPod. I would recommend that every serious audiobook aficionado get an iPod! They are not substantially more expensive, and they are worth it. The iPod is much better designed, and you get to use it seamlessly with iTunes. The one-two combination of iTunes and iPod blows everything else out of the water; that’s the reason I started writing these instructions.

Many public libraries now allow you to “check out” downloadable versions of audio books, just like checking out tape or CD versions, but more convenient. But they won’t play on an iPod! Is there a way to get them to play on an iPod?

The short answer is no, there is no way to get these versions to play on an iPod. The audiobooks are wrapped in a Microsoft Windows-only digital rights management (DRM) encoding, to prevent the books from being copied. Breaking the DRM to play the books on an iPod is illegal under current US law (as well as in many other countries). (Under US law, it’s even illegal to point at someone else’s instructions for breaking the Windows DRM. So, you’re not going to find that information here.)

Libraries want to be as accessible as possible to their patrons. That’s why they are experimenting with the current downloadable options. But IMHO the current solutions do not serve patrons very well (and I bet the libraries trying them out would say as much). It seems to me that it’s a poor use of taxpayer money to license digital versions of audiobooks which cannot be played on the handheld audio player with 80% of the market, and which surely pose technical challenges even for the patrons with devices that can play them.

I believe it is in everyone’s interest for libraries to instead acquire audiobooks in standard Audio CD format. These will be compatible with all players on all devices, including players that don’t involve a computer (which are a challenge for many patrons).

For iPod owners the best best is to pester engage in a dialog with our libraries about compatibility with the iPod, and request that they spend their audiobook budget on additional books on CD, which a wider range of library users can enjoy.

I have all my audiobooks on cassette tapes. Is there any way to get them onto my iPod?

It’s not impossible, but unfortunately there is no way I know of to directly import an audiocassette into iTunes. The reason CDs are relatively easy to import into iTunes, and then transfer onto an iPod, is because you can insert CDs into your computer and read the data off of them. It’s virtually impossible to buy a computer without a CD drive of some sort. But the same is not true of cassettes.

A couple of readers have pointed me at a tape player designed to be installed into a PC, called the Plus Deck ($150 at ThinkGeek). It looks like a pretty cool product, and while it doesn’t integrate directly with iTunes, you could probably use the included software to digitize tapes, and then drag the resulting files into iTunes easily enough. If you already have a sizable collection of audiobooks on tape, this could be a terrific solution. (If you try it out, please let me know what you think!)

If buying new, single-purpose hardware isn’t possible, or you’re on a Mac, some computers come with line in or microphone ports, to which you could connect a tape player, and then use the combo to re-record your tapes into digital form on the computer, but that takes additional software (Audacity is both free and well-regarded) and considerably more effort. At least for now, that’s not something I’m going to try, so I can’t document it, but these two guides may be useful. Update: Mac users, here’s a newer article that covers how to digitize both your cassettes and LPs.

There are certainly articles online that talk about converting cassette tapes to MP3s, which you could use as instructions (if you find a good set, let me know the URL, and I’ll post it here). Once you have MP3s of your cassettes, it’s a trivial exercise to add them to iTunes. Then you can add the audiobook meta information (title, author, etc.), and you’re off to the races.

My computer crashed, and I lost all of my audiobooks (or music, or whatever). Is there any way to copy them from my iPod back to my computer?

The folks at iLounge have covered this much better than I can, so I will simply point to their article:

Copying Content from your iPod to your Computer — The Definitive Guide

They have done a good job covering both Mac and Windows solutions, and keep the article up-to-date, critical given the changes that Apple’s iPod product line has been going through.

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