Category Archives: sync

How-To: Import Audiobook CDs to iTunes

If you’re like me, you probably have a stack of audiobooks on CD. While CDs are okay, I’ve been looking for a convenient way to get these audiobooks onto my iPod using iTunes for the sake of portability.
After some searching and tweaking, I think I’ve finally got this down to a science – so take a look at this tutorial, and enjoy listening to your books on the iPod!

(This seems to be a legal grey area – but as I understand the law in the US, you can make a copy of a CD you’ve purchased for your own personal use, which is what I’m doing. Please don’t use these instructions to break any laws in your country.)

What You’ll Need

  • A Mac computer* with OSX 10.4.x or better (last tested with 10.4.11)

  • iTunes 6.x or better (last tested with 7.6)

  • QuickTime Player 7.x or better (last tested with 7.3.1)

  • Join Together 5.1.5 (donationware)

  • Bonus: Apple ChapterTool and GUI-interface ChapterToolMe (if you want to make chapters in your finished audiobook)

Got everything installed? Great. Now for the steps:

In iTunes:

1. Navigate to Preferences > Advanced > Importing

2. Set the following preferences:

On CD Insert: Show CD (or Ask to Import CD, your choice)
Import Using: AAC Encoder
Setting: (Spoken Podcast will save you some time and file size, but I use High Quality, so I don’t have to switch settings for music CDs.)
Check Boxes: Automatically Retrieve CD Track Names from Internet (this will help, I promise!)
3. Insert the Audiobook CD you want to burn, and import it. If your Audiobook has multiple discs, import them all.

4. Find your Audiobook in your iTunes Library (click ‘Music’ on the left sidebar and scroll through).

5. Select all the tracks of the Audiobook (click the first, hold down the Shift key, and select the last).

6. Launch Join Together (if you installed the AppleScript that came with the app, select it from your AppleScript menu in iTunes. Otherwise, just navigate to the program in your Applications folder and open it).

In Join Together:

1. Make sure all the tracks are in the correct order (you may need to glance at your CD case to be sure – but if you got the CD track names from the internet as I suggested above, this should be easier!).

2. Type the author, title, and album as you want them to appear in your Audiobook list in iTunes. Some of this may auto-populate for you based on the CD track metadata.

3. Tweak your settings:

Data Rate: 32 kbps should be just fine for spoken word – increase this for better file quality, but a larger file.
Channels: Mono (again, this is fine for spoken word and will save space)
Sample Rate: I left this alone. Tweak as needed.
Save As: You MUST save it as a .m4b if you want to add chapters (see Bonus Section, below).
4. Hit ‘Proceed’, and your conversion will start.

In QuickTime:

1. Now QuickTime is going to start lining up boxes across your screen as it pulls each individual track from the CD together into one audio file. When it’s found all the files and started the conversion, you’ll get a progress bar, like this:

2. Depending on the size of your audiobook, QuickTime and Join Together should be doing their work for 20 minutes to an hour. Get a cup of coffee, read a book, keep yourself otherwise entertained for a bit.

Back in iTunes…

1. When the conversion finishes, open iTunes back up, and click on Audiobooks on the left sidebar. See your book?

2. If you want the audiobook on your iPod, plug it in and sync like you usually would, making sure to check ‘Audiobooks’ (or ‘All Songs and Playlists’) from the ‘Music’ tab.


That’s it! Once you’ve done this once or twice, you’ll get the hang of it (I know, it seems like a lot of steps at first!), and you’ll be listening to your books on your iPod in no time.

Solved! iTunes/iPhoto Sync Error -50

I’ve been fighting this issue for months and finally found a fix, so I thought I’d post what I learned to help others with the same issue.

The Problem:

Every time I tried to sync my iPhoto Library to my iPod, I would get an Error -50.
If I just synced my Pictures folder, it worked just fine. But I wanted to have my albums on the iPod.

Note: I know the Error -50 occurs for other reasons, so I can’t help you with that. But if you’ve isolated iPhoto as the problem, keep reading.

The Steps:

Under Pictures/iPhoto Library, you’ll find a file called AlbumData.xml.
Open this in a web browser. (For Firefox: File>Open Location)
If you get an error message (XML parse error, expected closing tag, etc.), continue.

Open iPhoto. Go to Preferences>Keywords.
Look through all these keywords and delete those with non-alphanumeric characters in them. (Mine had < and > characters, among others.)

Close iPhoto, then open your AlbumData.xml file in the browser again.

If you don’t get any errors this time, you’re good to go!


Remove all the photos from the iPod, in iTunes. (Devices>Your iPod Name>Photos>Uncheck ‘Sync Photos From’ and re-sync, removing photos when asked.)

Re-sync your iPhoto Library to your iPod. (Devices>Your iPod Name>Photos>Select ‘Sync Photos From: iPhoto’)
*Also, always connect the USB cable directly to the computer, not through a USB hub. This fixed several earlier issues, before the -50 error.


Look! No error messages! And albums are on the iPod!
Hopefully, this fixes this error for someone else out there.

My specs: MacBook, OSX 10.4.11, iTunes 7.5, iPod 80gb video (5th gen). Instructions may vary slightly based on OS, browser, and software versions.