How to extract media files from your iPod or iOS device

It’s always a good idea to back up your iTunes library. I do it somewhat obsessively, but there are simpler techniques that can do the trick as well.

But if disaster does strike and you lose everything, you may not be completely out of luck—assuming you’ve synced a good portion of your library to an iPod, iPhone, or iPad. In most cases, unless you’ve purchased something on one of your devices, Apple’s iTunes syncing is a one-way street—computer to device. But with some tricks and software, you can recover your music, videos, and more.

Pre-iOS devices

For certain iPod models—such as the iPod classic and iPod nano—there’s an easy way to copy all the content from your iPod to your Mac. Start by connecting your iPod to your Mac and immediately holding down the Command and Option keys until it’s mounted. (This prevents iTunes from syncing it automatically.) Next, download Titanium’s Software’s free utility Onyx. Launch the program, click on the Parameters icon in the toolbar, then on the Finder tab. In the Misc Options section, check Show Hidden Files And Folders, then click Continue in the warning window that appears. The Finder will restart, and you’ll be able to see hidden items.

Double-click on your iPod’s icon on the desktop, then navigate to the iPod_Control folder, then the Music folder inside that. Here you’ll find a number of folders named F00, F01, F02, and so on. Each of these folders contains media files—music, TV shows, movies—but they aren’t named the same way you’d see them in your iTunes Media folder. Which makes it hard to tell what’s what.

Although you may be able to narrow down items by their cover art (if it shows up), and determine songs or videos by playing them in the Finder, it’s more realistic to think of restoring your content via this method as an all-or-nothing endeavor. Drag all of the folders to your iTunes library, and once the files have copied over, iTunes will display the correct tags, and you’ll have all your files back. If what’s on your iPod is only part of your library, create a new playlist first and add the files to that playlist so you can sift through it and delete the files you already have.

Unfortunately, this method doesn’t work with everything. iOS devices don’t mount on the desktop, and therefore aren’t accessible in the same way. If you need to copy files off an iPod touch, iPhone, or iPad—or just want better control over the files—there is software that can do the job.

iOS and better control

Last year, we posted a roundup of iPod extraction tools. Of those, one of my favorites is the latest version of The Little App Factory’s $20 iRip app (you can copy up to 50 tracks for free to try it out). Launch iRip 2, hold down the Command and Option keys as connect your device to your Mac, and hold until it displays in iTunes. Next, if you have an iPod classic, nano, or shuffle, go to the iTunes’ Summary screen, check Enable Disk Use, then click Apply to make this change. (If you don’t, the iPod will unmount before you can do anything with it.) iRip then displays the contents of your device, with full names and metadata.

You can see the playlists on your device in the sidebar, and the different libraries that are synced to it: Music, Movies, TV, and so on. To restore your the contents of your device, select a library, click on the Transfer button, then choose to copy the selected item to a folder, to your iTunes library, or sync the device to your Mac. (You’ll have to copy each library separately.) You can also select a playlist, a single track, or any group of items to copy instead. If you’re looking for a specific file, use the Search field in the toolbar. You can also preview a file to make sure it’s what you’re looking for; select an item, then click the Play button at the bottom-left of the iRip window.

One minor problem with iRip is that it does not correctly display playlist folders and their contents. If you have a playlist folder, iRip shows it as a single playlist containing all of the items that are in the playlists within that folder. Also, you can’t restore actual playlists, only their contents.

I tested iRip will all of my devices—an iPod classic, iPod nano, iPod touch and iPad—and it had no problem with any of them. Copying is quick and safe, as you can choose a location to transfer the files, and don’t have to copy them to your iTunes library until you’re sure you want to. iRip is much more efficient than the Finder method I mentioned earlier, which requires that you copy files without knowing (at least easily) what they are, and it also works on all iPod or iOS devices.

Other uses

Being able to restore lost files from your portable device is great, but it’s not the only legitimate reason you might want to extract files. Perhaps you want to copy a movie from your iPhone to watch on your MacBook Pro while on the road. Or maybe you want to add a new album you downloaded directly to your iPad from the iTunes Store to your work computer (not the Mac you sync with, that is). Whatever the reason, knowing how to do so is a valuable tool in your media arsenal.

[Senior contributor Kirk McElhearn writes about more than just Macs on his blog Kirkville. Twitter: @mcelhearn Kirk’s latest book is Take Control of iTunes 10: The FAQ.]