Apple CEO Tim Cook (L) stands with Irish rock band U2 as he speaks during an Apple event announcing the iPhone 6 and the Apple Watch at the Flint Center in Cupertino, California, September 9, 2014.
Stephen Lam—Reuters
By Pat Regnier
September 16, 2014

It’s been pretty funny watching the reaction to Apple dropping a U2 “gift album” into everyone’s iTunes account. On Monday, Apple launched a special website just to make it easy to get Bono and the Edge off their phones and computers.

Somewhere in Cupertino, there’s a guy with an untucked shirt muttering, “But I thought people liked U2… People actually paid for 150 million of their records once… This one got 5 out 5 stars from Rolling Stone…1

So lesson number one is, the cool kids don’t like U2 anymore. But, hey, I have more than a few U2 songs in my iTunes library already. So let’s focus on lesson number two, which is that iTunes is a mess.

Some big-picture perspective before the whining: iTunes, and more importantly the iTunes music store, was in its time a marvel. It made music available on demand—and as single tracks, not on costly CDs—at a price lots of people were willing to pay.

But the software soon became the biggest pain point in your computer system. Adam Lashinsky at Fortune has the rundown here about how iTunes morphed from a music file manager into a “TV, DVD player, radio, DJ, college class and software store.” And, I’d add, Thing That Makes Me Terrified to Plug My iPhone Into My Computer. Click on that sync button, and there goes your afternoon.

From the beginning, with my first iPod, it’s always been the syncing that drives me a little crazy. Maybe there’s a Syncing Theory 101 class I could take to clear up what’s supposed to happen to my files when my iPod and now iPhone meets my Mac—Stanford could offer it as a MOOC. This may just reflect my age (see: owns many U2 songs, above) but it’s always seemed natural to me to think of my iPod/iPhone as a kind of Walkman with a very long mix tape on it. My Mac, to extend the metaphor, holds my virtual record collection.

Put another way, these things are, in my mind, two distinct “buckets.” I simply want to be able to take specific things out of the big bucket (the Mac) and put them on or take them out of the little buckets (the devices). iTunes will let you do that if you know how, but the whole syncing system resists the effort.

Instead of buckets, Apple seems to want me to think instead of a Platonic ideal media library, which all my devices would reflect in some way, so that when I changed my media in one library it would change everywhere. This was true even before the cloud-based iTunes Match, which really does create one big disembodied library untethered from my devices. Eventually, I gave up trying to control everything and signed up for Match. Which maybe is win-win: Apple gets my annual subscription fee and I can stop worrying about where my music is, because it’s all in the cloud somewhere.

Except I’m never sure that I get how it works, or how to make it so I have exactly the music I want when I can’t get online, or what’s going to happen to my files when I sync or try to update my OS. I’m just speaking as a consumer here—I’m not a technology writer—so I’m sure these are solvable problems if I spend enough time on Apple’s website. But the point is I don’t entirely know how to manage my music collection anymore (or, for that matter, my videos, my podcasts, my audiobooks, or—yikes—my photos). That’s fine when the music is on a service like Spotify or Apple’s own Beats, which I know from the start will vaporize as soon as I stop paying the bill or if the service shuts down. But I think of the stuff on iTunes media as my stuff. I’d like to control it.

Apple and Bono and the Edge just reminded everyone how tricky and effortful that is to do in the iTunesMatchCloudSync ecosystem. Especially, it turns out, when someone is determined to sell you something.

1 Other recent perfect albums, according to Rolling Stone: John Fogerty re-recording his hits with hip young acts like Kid Rock.

Related:
The Apple Store is Now the Last Place You Should Buy Your iPhone
New iPhones Sell for $2,000 on eBay, Asking Prices Hit $6,000
How to Sell Your iPhone Before the New Version Floods the Market

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