Hands on with iTunes Match: Frustrating, but rewarding

Apple (s aapl) officially launched iTunes Match on Monday, and things did not go entirely smoothly. I managed to sign up, and take the service for a test ride using a sandboxed segment of my iTunes library to see how it would handle iTunes purchases, ripped tracks and anything else I could think to throw at it.

A tale of two iClouds

I have a respectable library of around 15,000 songs, or about 100 GB of music from a mix of iTunes and CD purchases. With iTunes Match, I decided to ease into things using an account that has a respectable number of iTunes Music Store purchases, but on a machine that started off with zero ripped tracks in its music library.

While the activation of iTunes Match on this account from this particular Mac was rather quick — since the library was small — it wasn’t painless. After activating one of my iOS devices, I noticed right away that a little over half my music wasn’t added to my iTunes Match iCloud music library.  I made the mistake of assuming that iTunes Match would add my purchase history to my Match library, when it actually just uses your locally stored iTunes content. In the end, iTunes Match did recognize all of my iTunes music (once it was all downloaded to the computer I was using), but it would be in Apple’s interest to clarify this point.

Adding ripped music to iTunes Match

About 20 percent of my music library comes from just one artist: the Grateful Dead. I took the first ten albums in the infamous Dick’s Picks series and ripped them to my Mac’s iTunes library to see if I could have them matched.  iTunes Match performed well (assuming that’s because all the albums are available in the iTunes store), and started to match my ripped tracks as soon as they were added to my local iTunes music library.

I also added music I’d ripped previously by dragging the files to my iTunes library. As I was doing this, I checked the iCloud status of each track using the iCloud Status column, which you can enable in the View > View Options… menu.  Valid iCloud Statuses include Waiting, Error, Removed, Duplicate, Ineligible, Matched, Uploaded and Purchased.  You can create a Smart Playlist to keep track of which of your tracks fall into which iTunes Match category, as pictured above. Note that “Purchased” tracks, which are bought through iTunes, don’t count against your 25,000 song limit.
As each music file was added, I watched the status change from ‘waiting’ to ‘matched’.  This was the outcome I was hoping for. Six of the ten albums I matched has one or more tracks not matched, but they were uploaded instead, and thus still available via iCloud.
Uploaded not Matched
I tried everything to get iTunes to match all of my music, but there are some music files that it flagged as ineligible.  These are files that are either larger than 200 MB in size, have DRM from another music store or account, or were ripped at either a lower bit rate or to a format that iTunes doesn’t recognize.
To try to reduce ineligible tracks and increase matched vs. uploaded ones, I tried re-ripping problem songs from their original CDs to a higher bit rate. Despite my efforts, certain songs (which were available in the iTunes Store) just wouldn’t match. Hopefully the service’s ability to match tracks improves over time. In my opinion, 11 out of 189 songs being uploaded rather than matched isn’t a very good ratio, especially since the high bit rate of matched tracks is such a selling point of the service.
Missing Album Art
One last observation was that my album artwork wasn’t making the leap to the cloud immediately.  I’m kind of fanatic when it comes to album art, so at first this was troubling, but as time passed, I noticed that some of the covers started appearing.  I probably just need to be a little patient as iTunes Match catches up with demand. It’s good that Apple is prioritizing music uploads over artwork, too, if it comes down to a choice between the two.

Deleting, then downloading matched music

I recall a time when you could pay a company to rip your music collection for you. Apple’s iTunes Match is sort of like that, in that it takes your existing collection and provides you with a better, more usable version, which is exactly why I wanted to delete my source library and rebuild it using Apple’s higher-quality cloud-based tracks.

To test out how it would work, I went to a single album that had all of its tracks matched in my iCloud library, and deleted them.  I was careful not to delete the music from iCloud, too. Rather, I deleted the music from my local iTunes library without ticking the box next to “Also delete these songs from iCloud.”  The music was not actually removed from my library, but the status of the tracks I removed changed to reflect their presence in the cloud but not in local storage. Upon re-downloading, all of my 128 Kbps music files had been replaced with a collection of 256 Kbps music files.

Two conclusions

If your library is composed of mainly iTunes-purchased music, then I think you will enjoy what iTunes Match has to offer. Beyond simply keeping your music files in the iCloud, you’ll also be able to manage and share a set of playlists. This is a value-add feature that you can’t get by just downloading your previously purchased music from the iTunes Store. Plus, if you have a lot of legacy iTunes tracks with DRM, this is a good way of getting rid of that protection without having to pay per track to upgrade with iTunes Plus.
If, on the other hand, you have a substantial music library built mostly through ripping, then you may find yourself having to do a significant amount of pruning to get it in good enough shape to take full advantage of iTunes Match. After getting past the initial ordeal, however, I think most music fans will enjoy the cloud-based convenience features that iTunes match has to offer.