The Promise And Failure of iTunes Match

There is no doubt that Apple is a brilliant company—especially over the past decade. The ecosystem that was developed initially around music via the iTunes store and the iPod which evolved by adding film & television, enhanced video capabilities of the iPod, finally culminating with the App Store and iPhone/iPad was a masterful strategy.

The syncing latency with iTunes Match is shockingly bad

I fell perfectly into Apple’s plan, as many of us did, by building a music library in iTunes and integrating my own media and behavior into their ecosystem. Eventually, not only did I store and meticulously organize hundreds of gigabytes of music—literally thousands of albums, tens of thousands of songs—in iTunes, I turned to devices created by Apple to play them. Over the past dozen years I have owned and used 3-4 iPods, 3 iPhones, 2 iPads, 3 MacBooks, an iMac, and an Apple TV.

Unfortunately, managing an enormous media library across multiple devices started to become a chore. With the advent of cloud computing & storage and the success of streaming music services, I anticipated Apple’s next move in their brilliant ecosystem. I was very pleased when they announced iTunes Match.

With iTunes Match, all your music — even songs you’ve imported from CDs — can be stored in iCloud. So you can access your music from all your devices and listen to your entire library, wherever you are.

For only $25 per year, Apple promised all of my music, synced across all of my devices. Or so they said…

iTunes Match is Broken

I’m six months into my second year as an iTunes Match subscriber. Obviously, I’ve given Apple time (and $50) to work out some of the kinks. With recent updates to iOS and iTunes, it feels like iTunes Match is only getting worse.

First of all, there is no way to manage music on your individual mobile devices. The ability to select and manage specific songs, artists, and playlists is removed from iTunes once you opt into iTunes Match. You may download specific songs, albums, and artists via your mobile device, but there is no means of removing individual songs once they’re on the device. In other words, when your 16GB iPhone starts to get too full of apps, pictures, movies, and music, you can’t remove a few albums/playlists to clear up space. With iTunes Match enabled, your only option is to remove all of the music, and start fresh—re-downloading the albums that you want on the iPhone. Needless to say, this is tedious and very poor planning & design by a company defined by its brilliance in this space.

Playback via the native Apple mobile Music app sometimes completely fails

My next issue with iTunes Match is the inability to stream music that you own. The music must be downloaded onto the device. If you have a weak wi-fi or cellular connection, you’re going to have a very difficult time accessing any music that isn’t already loaded onto the device. Additionally, any music that you want to listen to must be downloaded and stored on the device—taking up space on the hard drive—rather than being streamed over an Internet connection like Pandora, Last.fm, Rdio, Spotify, etc.

The syncing latency with iTunes Match is shockingly bad unless you purchase music directly from the iTunes store. If you rip a CD or import a song to your library that doesn’t come from iTunes (especially a song that may not be part of the iTunes catalog) it can take a very long time (sometimes more than a day) for it to show up in iTunes Match. This may not bother many people, but, as someone whose musical taste tends to go off the mainstream map, it is problematic. If I discover a new artist, download their music, and import it into my iTunes library, it needs to be accessible across all of my devices within seconds or minutes—not hours or days.

Finally, playback via the native Apple mobile Music (iPod) app sometimes completely fails. It fails to recognize which songs are downloaded onto the device which in turn causes the app to attempt to play all of the music (in my case thousands of songs) in the library. The app skips one-by-one from track-to-track several times per second, attempting to find a file that is stored on the device. There is also a bug that hides the download button on music that isn’t stored on the device, making it impossible to download songs that you may want to play. I suspect this is related to the poor (lack of) music management functionality, and the all-or-nothing approach to maintaining files via iTunes Match.

To summarize, I gave iTunes Match a fair shake, yet continue to be disappointed. A couple months ago I decided to pony up the $10/month for Spotify Premium. I don’t love the fact that I don’t actually own any of the music, I still have to use iTunes to build and manage playlists, and it costs nearly $100 more per year. But it does what I need it to do; it delivers the music I want to hear when I want to hear it. This will be my last year as an iTunes Match subscriber unless they take some major steps to improve the product over the next few months (or acquire a proper streaming service).

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