The newest versions of iTunes allow users to transfer purchased tracks to authorized computers.

2009 HowStuffWorks

iTunes Music Settings

­Manipulating the iPod for something it isn't intended for -- transferring music to a computer -- is naturally a bit harder than finding your favorite Madonna album to jam to during­ a workout. For that reason, it's helpful to understand a few basic settings and functions before you start to hunt down music files within your iPod hard drive. Particularly if you're looking to refill an empty iTunes library, these tips can prevent you from losing your music.

There are three ways that iTunes can communicate with your iPod:

  • Automatic updates: iTunes automatically adds new downloads to the iPod whenever connected.
  • Auto update select playlists: iTunes automatically downloads new playlists to the iPod whenever connected.
  • Manually manage: You tell iTunes what and when to update the iPod.

­When recovering an iTunes library, only work in manual sync mode. In an auto sync library, iTunes will begin updating your iPod without prior warning. To stop the program from auto syncing, hold down SHIFT+CTRL (on Windows) or CMD+OPT (on a Mac) until the iPod icon appears in the source list [source: Hollington].

Apple tossed out a bone when it came out with the Transfer Purchase feature on iTunes 7. Beginning with that version of the program, users could automatically transfer songs they purchased from iTunes from their iPods to authorized computers. To play content that you buy through an iTunes account, you must authorize the computer with your iTunes username and password.

Another new feature is iTunes Plus. Downloads included in this program have no digital rights management (DRM) encryption. That means you can transfer them to as many iPods, computers and CDs you desire. 

But let's say you want to transfer purchases you bought on a Mac to a PC. Mac-formatted iPods aren't compatible with Windows operating systems. If you're working between systems with a classic, nano or mini device, it's helpful to know which one your iPod is formatted for. To find this, select About in the iPod's Settings menu. If you scroll to the bottom of a screen, you'll see either a list of serial numbers that denotes a Mac format or Format: Windows [source: Apple].

Now that we know a little more about how the iPod functions, it's time to learn how to use it to transport files.