Originally Posted by Fugazi
I know that in some instances, it's either not possible or more difficult with songs that weren't purchased with iTunes. I'm pretty sure I read it somewhere on an Apple help page about transferring music from an iPod to a computer.
If you have music not purchased from Apple, it is a big pain in the rear. I still need to move my songs to my new iPhone 5 but I dread it. I'm not a fan of iTunes in general. It is more like a complicated/bloated Windows product than an Apple product.