How to Remove DRM From Your Music With iTunes Match
In the heyday of illegal music-sharing services, iTunes was a beacon of light to the recording industry because Apple's service incorporated Digital Rights Management (DRM) to discourage piracy. Now that DRM for music is largely a thing of the past, how can you cost-effectively free your music from Apple’s Fair Play protection?
In this tutorial, I’ll provide an inexpensive workaround that makes stripping DRM easy by employing Apple's iTunes Match service.
Why Does It Matter
If you’re used to keeping your media and digital life within Apple’s ecosystem, you may have never noticed the impact of DRM. Step outside of Apple TVs, iPhones, and iPods, though, and its annoyance quickly becomes evident.
You cannot upload a protected song or album to Amazon Cloud Player or Google Play Music, play the song on an Android device, or move the song to a new computer without authorizing that computer with your iTunes account. In short, it aggressively limits the flexibility of the music you purchased.

The Old-Fashioned Way
When Apple began removing DRM from its library of songs in 2009, it offered users the ability to pay $.30 per song to upgrade from the protected song to a better quality 256-kbps version without DRM protection. Depending on the amount of protected music you have, that could be a costly venture.
A less-costly, but time-intensive way to strip the DRM is to burn all of the protected music to CDs, delete the protected versions, and then re-import the songs from the burned disc. Now, though, there’s a better option.
Matchmaker
With the introduction of iTunes Match, a service that creates 1-for-1 copies of your iTunes library in the cloud, removing DRM from your music is easier than ever. The service is $25/year, but you should only have to do this process once as iTunes music purchased from 2009-on no longer has DRM protection.
Step 1: Back It Up
Before you begin, back up your current music library to an external hard drive or USB drive. This can be done by dragging the iTunes folder from your Mac’s Music folder to the backup drive.
Step 2: Identify Your Protected Tracks
The newest version of iTunes has removed some of the song attributes from the library area so the method for sorting your music beyond artist or album isn’t immediately evident. To find your DRM-laden tracks, you need to add Kind as an attribute. Click View > Show View Options and put a tick next to Kind under the File subheading of the dialog box.
Exit the dialog box, and then click Kind in the header area of your music library to sort the songs accordingly. Scrolling through your listing, you should see a number of songs with Protected AAC audio file listed as the file kind. These are the tracks with DRM protection.
Step 3: Here Goes Nothing
To turn on iTunes match, select Store > Turn On iTunes Match from the iTunes menubar. iTunes will confirm that you want to pay the $25 fee before continuing. When you’ve accepted the charges, iTunes will begin matching your music.

The process is fairly swift, though the speed of the matching process relies on your music library size/origins and your Internet speed. Of the 1878 songs I had, 1600-plus were matched quickly, while the remainder needed to be uploaded to iCloud since they were specialty tracks or were improperly named.



Step 4: Slash and Burn
Once your music has been matched successfully, return to your iTunes library sorted by Kind. Highlight all of the Protected AAC music by clicking the first song and then, while holding Shift, clicking the last song in the list. Next, press Fn Delete to remove the protected songs from your library. If asked, choose to move the songs to the Trash.



When they’ve been deleted, empty the Trash.
Step 5: Back From the Dead
Next to the songs you just deleted, you should now see a small cloud icon has been added to the right of the song names. Click the cloud icon in the attribute bar to sort the songs by iCloud.



The songs you previously deleted should all be listed with a Download from iCloud icon beside them, indicated by a cloud with a down arrow superimposed on it. To re-download them all at once, highlight all the songs using the Shift click method above, Ctrl click, and then choose Download from the menu.
All the songs should be returned to your iTunes library with a new designation of < strong >Purchased AAC audio file as the file kind.

Conclusion
When I sorted my library by file kind, I had 124 DRM-protected songs. Using the old method of paying $.30 per song, it would cost $37.20 to update my library. The savings will indubitably be much greater for users with large DRM-protected libraries. Ultimately, it’s difficult to accept the concept of re-buying your music to remove the DRM, but using this tutorial, you can now do so cost-effectively and net yourself a year of iTunes Match service as a bonus.