Q: I’ve purchased a lot of music from iTunes over the years, going back almost to the day the iTunes Store first opened. A lot of my stuff is in the older DRM’ed format from before iTunes started selling DRM-free music. Now I hear that I can take advantage of the new iCloud features to upgrade my older music and make it DRM-free, but the whole thing has me a bit confused. Can I just convert stuff through iTunes in the Cloud? Do I need to subscribe to iTunes Match? When I download old songs from my “Purchases” some of them seem to come in as higher-quality DRM-free tracks, while others are still the same old 128kbps DRM-protected tracks. I don’t get why there’s a difference. iTunes Match says it’s supposed to convert everything, so does this work better if I actually subscribe to iTunes Match or would I just be wasting my money?

– Dave

A: Although they may seem similar, iTunes in the Cloud and iTunes Match are actually completely distinct services and therefore behave somewhat differently in terms of your purchased items.

iTunes in the Cloud

iTunes in the Cloud is a service that allows users to re-download certain types of previously purchased content from their iTunes Store account. It also provides the ability to have new purchases downloaded to one or more computers or iOS devices automatically as soon as the purchase is made, rather than having to wait to sync all content via the iTunes application. This service is essentially free, although since it only applies to purchased content, you obviously must have actually purchased something from the iTunes Store to be able to take advantage of it.

Since you’re actually just re-downloading from the iTunes Store’s inventory, previously purchased content is only available from iTunes in the Cloud if those items are still available on the iTunes Store. Basically, if the iTunes Store isn’t selling something, then chances are you won’t be able to re-download it either.

There is one small exception to this, however, when it comes to older DRM-protected tracks. In 2009, Apple began selling all of the music on the iTunes Store in a 256kbps, DRM-free format. The implication at the time was that this was a wholesale conversion of the iTunes Store music catalogue over to the newer DRM-free format, however in reality many tracks were actually not directly replaced with the newer versions; often the prior albums were re-released as different editions or “deluxe” versions, and in some cases tracks or albums were removed from sale entirely, likely due to licensing agreements with the music labels.

With millions of tracks on the iTunes Store, Apple is pretty much forced to rely on internal IDs to identify content, kind of like catalogue numbers. When you re-download a track you’ve previously purchased, iTunes gives you the exact track that you previously purchased—not necessarily “exact” in terms of the identical file, but rather whatever item has the same “catalogue number.” This could be in the same format you originally purchased, DRM and all, or it could have been replaced with a newer, 256kbps DRM-free version. Essentially, you get whatever is now in that “slot” in the iTunes library (this is also why in a few rare cases users have actually gotten a completely different song when re-downloading a previous track).

On the surface it would seem that if a previously purchased track is being sold on the iTunes Store in the new, DRM-free format, you should also be able to re-download that DRM-free version from your purchase history. Unfortunately, if you look closely you’ll see that in many cases the newer track or album on the iTunes Store isn’t exactly the same as what you purchased. For example, if the “iTunes Plus” edition of a track was released as a new edition or as a “deluxe” album, this will technically not be the same song you have in your library. The same can happen with albums where both “Clean” and “Explicit” versions may exist, yet one is no longer available. Sometimes, this isn’t even obvious as the artist, album and track information may look identical, but the album was published on the iTunes Store as a new entry—with a new “catalogue number”—rather than a direct replacement for a previous title.

iTunes Match

iTunes Match is a much more comprehensive, paid service that not only makes your purchase history available, but also matches whatever else it can from your library and uploads the rest. The end result, in theory, is that your entire iTunes music library is made available in the cloud.

However, a key point is that unlike iTunes in the Cloud, iTunes Match basically excludes any DRM-protected purchases from your purchase history, choosing to try and match these to the iTunes Store instead. Since this process uses a matching algorithm rather than reading your purchase history directly, it is able to pair up your existing DRM-laden 128kbps tracks with newer 256kbps DRM-free versions wherever possible, even if the edition/catalogue number has changed. In fact, since iTunes Match matches tracks rather than albums, it can even pull a 256kbps DRM-free version from a different album if it’s not available in the album that you have it in. This is why iTunes Match sometimes only appears to match a few songs on an album in your library—the specific album isn’t available on the store, but the exact same tracks are included on other albums by the same artist. It’s actually not uncommon to see a scenario where your specific album may only be available from your purchase history in the older DRM-protected format and not sold on the iTunes Store at all, yet iTunes Match is able to match up at least some of the tracks as DRM-free 256kbps AAC versions.

Keep in mind that iTunes Match ignores your 128kbps DRM-protected purchase history entirely; any protected content you have that cannot be matched up with a 256kbps DRM-free track will simply be uploaded to iCloud exactly as-is, DRM and all. This has nothing to do with your purchase history—it’s the same way all unmatchable tracks are handled by iTunes Match.

Note that the iTunes Match process does not replace the content that is in your original, source iTunes library. Although any matched tracks “in the cloud” will be 256kbps DRM-free versions, you will still have the original 128kbps DRM-protected version in your own iTunes library. There is no automatic “upgrade” of the tracks in your source library to the new versions, regardless of how these tracks are matched. The same applies to tracks from your own CDs and other sources—these will be matched with 256kbps AAC versions on the iTunes Store wherever possible, but the matched versions do not replace your original, local copies.

If you download a matched track to a secondary iTunes library, however, you will get whatever version the iTunes Store has matched it with—meaning the 256kbps DRM-free version. Similarly, if you were to delete the track from your original iTunes library, you could re-download the “matched” version in 256kbps AAC format.





Jesse Hollington was a Senior Editor at iLounge. He's written about Apple technology for nearly a decade and had been covering the industry since the early days of iLounge. In his role at iLounge, he provided daily news coverage, wrote and edited features and reviews, and was responsible for the overall quality of the site's content.