The iPhone 2.1 Audiobooks Bug [+Workaround]
By Daniel Miessler on September 20th, 2008: Tagged as Apple | iPhone

Image from duke.edu
There is a bug in the iPhone 2.1 software that only lets you have around 19 or 20 audiobooks at a time. If you have more than that the iPod application will die when you click the audiobooks icon on your phone.
This sucks a lot.
There is a workaround, however, which is to create a playlist and drag all your audiobooks into it. Go into your music sync settings and sync that playlist to your phone, and you’re set. It’s lame, but it works.
Hopefully they’ll fix this in the next minor release—along with the dropped call issue people are still having (which I find absolutely unacceptable, by the way).