iTunes' Black Mark

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Last week Slim Devices announced the new Squeezebox2, an impressive digital-music player that connects to your network and your home stereo. But however impressive its features (and they are impressive), the company can’t escape the one question it can’t answer “yes” to: Does it work with songs from the iTunes Music Store?

The answer from Slim Devices is “no,” of course. As is the answer from every company whose name isn’t Apple. At this point the only external music player that will play iTunes Music Store files is the AirPort Express, a device without a display or a built-in remote control.

I don’t want to fault the AirPort Express. It’s a cool product, for what it is. But it’s not in the same league as Squeezebox or Roku Labs’ series of SoundBridge products, both of which let you browse your music library from your couch with the help of a bright fluorescent display and an infrared remote.

Unfortunately, iTunes Music Store patrons who want to use Slim’s or Roku’s players have to jump through hoops to play their legally-obtained music. They can burn tracks to an Audio CD, then rip the tracks right back into MP3 format. Or they can take a trip down the legal rabbit hole with Hymn, a utility that strips Apple’s copy-protection off of the files. I’ve tried both, and both work — but it’s a pain.

And the sad truth is, there’s no technical reason it needs to be this way. Based on various conversations I’ve had over the past year, I’d wager that both Slim Devices and Roku Labs could iTunes-Store-enable their music players in a matter of hours… if doing so didn’t put them in the crosshairs of a massive legal barrage from Apple’s lawyers.

Under the Digital Millennium Copyright Act — a horribly constructed law for consumers and engineers alike that we can hope will one day be repealed or found to be unconstitutional — it’s illegal to create software to circumvent copy protection. So unless a Slim Devices gets Apple’s blessing, such a company can’t decrypt Apple’s music files… even if everyone under the sun knows how to do it.

It’s enough to make you want to rage against Apple. Why stifle consumer choice? In the case of Squeezebox2, the device is smart enough to (like the iPod) decrypt the files itself after they’ve streamed over a network. There’s no risk of unencrypted files being intercepted. And this sort of restriction has already proved to be ridiculous, because Apple’s security is strong enough to prevent casual file-sharing, but weak enough that someone who really wants to steal music can do it.

That said, what if we’re wrong about attacking Apple on this point? I’ll grant you, if Apple refuses to deal with companies such as Slim Devices specifically because it wants to retain a complete monopoly over the hardware and software of the iPod-iTunes platform, Apple deserves all the lumps it gets on this issue. The biggest problem with digital rights management (DRM) technology is that the DRM gets in the way of legitimate uses of regular consumers. By preventing iTunes songs from playing on Squeezeboxes, Apple is making its DRM a visible barrier… rather than an invisible threat against those who would steal music. (You could make similar arguments for why Apple doesn’t want any non-iPod portable players to play music from the store.)

But what if if Apple’s obstinance in this matter has nothing at all to do with keeping its monopoly in place? Consider the state of affairs when Apple launched the iTunes Music Store: Steve Jobs and company had negotiated a deal with all the record companies, and demanded that (in the interests of a good user experience, Apple’s hallmark) every track cost 99 cents and just about every album cost $9.99.

What if, as a part of those negotiations, Apple had to agree to extremely strict licensing arrangements with the music industry. If the company’s license specifically limited them to playing back songs on a computer, on an iPod, and on a “remote speaker” attached to a computer (read: AirPort Express), then it could be that Apple won’t let hardware from other companies play its files because it’s not legally allowed to. (Which would be unfortunate, since Microsoft clearly has license to play back tracks encoded using its technology with a host of portable devices.)

I don’t know if it’s true or not. If it were true, it would mean that Apple’s not operating from the Microsoft playbook — and we’d all like to think better of Apple, wouldn’t we?

But in the meantime makers of exciting music products are being given the cold shoulder by Apple, their products bearing a black mark (“Not compatible with the most popular digital music store on the planet!”) that they don’t deserve. And their customers are left jumping through hoops in order to play back the music they rightfully paid for. It’s a real shame.

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