Get songs and playlists off the iPhone
Apple's iTunes software makes it dead-simple to copy music onto your iPod, but when it comes to moving files in the opposite direction--from the iPod to your computer--there's no obvious solution. I get an e-mail on this topic at least once a week, usually from someone who's had his laptop stolen or watched helplessly as his hard drive crashed. After an incident like that, it can be a relief to know your music collection (or at least part of it) is backed up on an iPod.
Of course, relief can quickly turn to frustration when you plug that iPod into a new computer and can't figure out how to grab those files. Worse yet, iTunes will sometimes prompt you to erase the iPod if it's not recognized. Saying yes will only end in tears.
To be fair, iTunes isn't completely useless when it comes to pulling media off your iPod. Under the iTunes File menu, there's an option for "Transfer Purchases From iPod" that will work to pull any content purchased through the iTunes Store back to your computer. It's a nice place to start, but to get the rest of your content off your iPod, you'll need to download some additional software.
There are two very useful applications out there that will transfer the rest of your music, videos, playlists, and metadata off your iPod and back to your computer. In truth, there are dozens of programs that can accomplish the same thing, but for the sake of simplicity, we'll stick with these two since they're easy to use, and work with all models of iPods and iPhones.
Update: an updated version of Pod to PC (version 3.02) offers compatibility with iPhone OS 3.0 but requires a $9.95 activation fee. The original, free versions of the software outlined in our slideshow and video are still available using the Download.com links below, however, they are not compatible with iPhone OS 3.0.
Depending on the type of computer you're transferring to, download Pod to Mac or Pod to PC from Download.com. If you're looking to get photos off your iPod, go ahead and download Pod Photo Transfer (PC only), as well.
To see how the process works, CNET's Tom Merrit made a handy video that walks you through the steps for retrieving files from an iPhone. The process is identical for iPods, so don't feel left out when Tom says "iPhone"--just overdub it in your mind with the iPod model of your choice. For a few extra iPod media transfer tips, check out our CNET slideshow.