Keep an iTunes music library in the cloud and upgrade existing tracks for $24.99 per year with iTunes Match.

There haven’t been any truly significant advances with iTunes music since Apple unshackled songs from the FairPlay digital rights management ball and chain in early 2009. That all changed with the recent introduction of iTunes Match, a new scan-and-match subscription service offering access to your entire music library from any Mac, PC, or iOS device which can also upgrade matched tracks to higher quality versions, regardless of where you acquired them.

What You’ll Need:

>> iTunes 10.5.1 or later
>> $24.99 subscription to iTunes Match

Difficulty: Medium

1. Signing Up

Subscribe to iTunes Match in a few clicks, then enjoy a year of having your music everywhere for only $24.99.

While iTunes Match is part of Apple’s iCloud service, it isn’t free. You’ll need to sign up for an annual subscription of $24.99 with the same Apple ID you use for iTunes purchases, which can only be done from iTunes 10.5.1 (or later) on a Mac or PC. From the Store menu, choose Turn On iTunes Match, then click the blue Subscribe for $24.99 Per Year button. Enter your Apple ID and password to confirm, click Add This Computer, and sit back while iTunes takes care of the dirty work for you.

2. Scan, Match and Upload

After you sign up, iTunes Match will commence with a three-step process to get your music library in the cloud.

iTunes will now perform a three-step process. First, iTunes gathers information about your music library, uploading the results to Apple’s servers. Second, your music is matched against more than 20 million tracks already in the iTunes Store. Finally, iTunes will upload tracks it couldn’t match, which is the lengthiest part of the process for most of us. You’ll want to set aside a few hours for iTunes to do its work just in case, but you can shut down and pick up again at any time, and continue to use iTunes while Match works in the background.

If you have more than 25,000 tracks, iTunes Match won’t work - at least, not unless you delete tracks to hit that magic number or disguise them as podcasts (which are ineligible) by choosing File > Get Info (or Command-I) and changing Media Kind to Podcast in the Options tab. The service also limits individual tracks to 200MB or less, and songs with DRM will be matched and uploaded only if your computer is authorized to play them in the first place.

3. iCloud Status

A handy chart on Apple’s support website shows the five types of iTunes Match icons that may appear.

iTunes Match really begins to strut its stuff with the new iCloud Status column. To turn it on, select the Music library (or any playlist) in the sidebar, choose View > View Options (or Command-J), and select iCloud Status in the middle column. Click OK and the iCloud Status column will now show at a glance whether a particular track is Purchased (bought from the iTunes Store and most likely already 256Kbps), Matched (available to download or upgrade), Uploaded (no upgraded version available), or Not Eligible (not a music track or its bit rate is below 96Kbps). Other status icons include Error (for corrupted tracks or upload problems) and Waiting (for tracks yet to be matched).

To quickly identify matched tracks, use the View Options dialog to turn on iCloud Status.

4. Smart Playlist to the Rescue

The easiest way to find and download matched tracks is to create a Smart Playlist such as the one shown here.

The first thing you’ll want to do is upgrade old tracks to higher-quality 256Kbps DRM-free AAC format from Apple’s servers. The easiest way to find and replace these matched tracks is with a Smart Playlist; to create one, choose File > New Smart Playlist and enter the settings shown here. The goal is to find all files with a Bit Rate less than 256Kbps whose Media Kind is Music. Add “Any of the following are true” by holding down the Option key while you click the + button after the second row, then add “iCloud Status is Matched” and optionally “iCloud Status is Purchased” in case you still have older 128Kbps tracks hanging around that were never upgraded via iTunes Plus. Click OK and you’ll be prompted to name the new Smart Playlist in the sidebar, and presented with a list of qualified tracks.

5. Purge a Track

To delete a matched track, use Option-Delete and move the old media to the Trash.

Now that we’ve narrowed down tracks eligible for an upgrade, it’s time to delete them. While purging your precious music might sound nerve-wracking, iTunes Match makes it a snap. The actual media gets deleted, but your artwork and metadata—including play counts and Last Played data—remains intact, even after downloading the new media. Select a track in your new Smart Playlist as a guinea pig, hold down the Option key, and press Delete. iTunes will ask for confirmation; click Delete Item and then Move to Trash, which removes the track from your iTunes folder but keeps it available should something go wrong.

The selected track remains in your iTunes Smart Playlist, but there’s now an icon in the iCloud Download column. Click it and the track will be downloaded from iCloud in 256Kbps DRM-free AAC format, regardless of its original format. After doing this, the track will vanish from your Smart Playlist (thanks to the “Live updating” feature), but it remains in your library as well as any previously assigned playlists.

6. Delete and Download En Masse

Easily download multiple tracks with the Control key and a shortcut menu.

Now let’s move on to deleting the rest of your matched tracks. This can be done a number of ways: a few at a time (useful for confirming successful matches as you go), an album or artist at a time, or even the entire Smart Playlist, all at once. Select multiple tracks and repeat the Option-Delete shortcut above. Worried you’ll sprain a finger clicking each individual track for download? Fear not! Select the tracks again, hold down the Control key, and choose Download from the shortcut menu. Now sit back and let iTunes pull the tracks down from iCloud, one after the other.

7. Add Other Devices

Turn on iTunes Match on your iOS 5 device, and all of your cloud-based music will be available for download.

The real beauty of iTunes Match comes when you add other devices—be they additional Mac or Windows computers, or any iPhone, iPod touch, or iPad (running iOS 5 or later). Sign in to the iTunes Store with the same Apple ID, turn on iTunes Match, and that device will now have access to your entire iTunes library. Download individual tracks and entire albums, artists, or playlists as needed, from anywhere there’s an internet connection.

From your Mac or PC, choose Store > Turn On iTunes Match, then click Add This Computer to get started. From any iOS 5 device, go to Settings > Music and toggle iTunes Match on; if you prefer to view only tracks that actually reside on the device, turn off Show All Music, which by default will display everything available on iCloud. If you have favorites you’ll want to always keep on the device, it’s faster to sync these tracks via iTunes prior to turning on iTunes Match.

8. Convert and Quit

Once matched and upgraded, tracks are yours to keep even if you discontinue iTunes Match—but they’re tagged with your Apple ID, so you might not want to pass them on to others.

If you have ancient tracks in your library encoded at a bit rate of 96Kbps or less, iTunes Match will ignore them—but there is a workaround. Select the songs and choose Create AAC Version from the Advanced menu, making sure your encoded quality (Preferences > Import Settings) is over the threshold. Once matched, simply delete them and download the upgraded versions, same as before. Upgraded tracks are not protected by digital rights management, so they’re yours to keep; quitting iTunes Match simply ends your ability to match further tracks or access them via iCloud.