How to Transfer Your iTunes Library to an Android Device

Apple’s walled garden can be a nice place to live. But at some point, you may want to venture beyond the cozy confines of Cupertino’s ecosystem. Unfortunately, that’s when you could find yourself straying into the battlefield that is the ongoing Apple-Google skirmish. And you’ll probably find yourself asking the following question sooner than later: How can I pack up my iTunes music library and move it to a device from Apple’s arch nemesis Google?

San Francisco-based doubleTwist’s doubleTwist Player offers a truce, of sorts. The company’s free Android application (current version: 1.7.2), coupled with its free Windows and Mac desktop software, copies your iTunes music and video to your Android device—with a few limitations.

Let’s start with the “free” part. Yes, the doubleTwist Player app lets you transfer content to your Android over USB. But if you want to sync wirelessly, you’ll need the not-so-free doubleTwist AirSync app ($5). Want to download album art or subscribe to podcasts for automatic downloads? Those are premium features as well that cost $5 each. Your best bet: Download doubleTwist Player and upgrade within the app to doubleTwist Pro, which gives you all those features for $10. It’s worth the price. (The screen shot below shows the Android app in play mode.)

But back to those limitations. Be aware that any iTunes music or video protected by DRM won’t be transferred. This applies to songs you purchased in 2009 or earlier, before Apple discontinued its music DRM. In iTunes, you can upgrade purchased songs with DRM to “iTunes Plus,” which strips away the restrictions. Also, the doubleTwist desktop software lets you know which content is protected by displaying a padlock icon next to any content with DRM.

Another heads up: You can’t copy over TV shows or movies acquired through iTunes, either. Videos of your own making, however, will cross the divide, though the process isn’t entirely intuitive. In the desktop app, you must click on “Videos” under “LIBRARY,” find the video file you want, drag it to a new or existing playlist, click your Android device’s name under “DEVICES,” click the checkmark box next to “Sync videos to device,” find the playlist by checking “Selected Playlists,” click to select the playlist by name, then click the “Sync” button.

To recap: There’s a fair amount of setup, the free app will probably end up costing you money, and you still can’t copy over everything in your iTunes library. Also, doubleTwist Player isn’t the only app of its kind—Highwind Software LLC’s TuneSync ($6) and JRTStudio’s iSyncr for Mac and iSyncr for PC ($3 each) are other options. All that aside, if you’re a music lover moving from iOS to Android (or toggling between the two, as I do), this app ultimately does a nice job of helping you scale Apple’s garden wall—even if you have to leave a few things behind.