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iPhone owners can now buy ringtones for 99 cents, with some pain

iTunes now allows you to download ringtones and convert some of your existing songs to iPhone ringtones, assuming you don't use the widely circulated hacks to avoid the fee.

The iTunes Store now allows you to download ringtones and convert some of your existing songs to ringtones, assuming you (a) have an iPhone and (b) feel like giving Apple 99 cents each time you do it.

As we all know, (b) is now entirely optional. My colleague Seth Rosenblatt at Download.com has written about using your existing songs as ringtones without having to donate to Steve Jobs' retirement fund. iTunes 7.4.1 requires a slightly different hack, but it's still possible.

The conversion process is somewhat clunky, but at least unlike competing ringtone-download sites you get to select the clip you want.

Which is as it should be. Then again, even though it's possible to install Linux on your iPod, we doubt many people are buying them to run Tetris. This post, in other words, is written for the vast majority of people who don't mind spending a dollar for a ringtone.

I tested my iPhone with two ringtones created by Apple's ringtone generator. The bottom line is that while it does work, it's somewhat clunky and the inability to use your own legally purchased songs transferred from CDs is a severe drawback.

Why was it clunky? First, iTunes was unable to detect which songs in my library could be converted to ringtones. It caught some of them, but not all. (A new column with icons shaped like bells denotes which qualify.)

It also coughed up a confusing error message when I tried to convert a song from a legally purchased CD: "You can create iPhone ringtones from many songs purchased from the iTunes Store." Nowhere does it clearly say that my CD-origin song didn't qualify for conversion. A better iTunes interface would entirely disable that conversion option for non-qualifying songs.

So I picked an iTunes-purchased song that did qualify for the honor of ringtone-ization. The process itself was straightforward enough, and to Apple's credit, it's pleasant to select what part of a song you'd like to use for a ringtone (as opposed to have someone else do it for you and charge you more, too).

Here's an almost-entirely unhelpful error message you get when trying to convert legally purchased songs transferred from CDs to iPhone ringtones.

But another bit of clunk extruded itself when my new ringtones failed to appear on the iPhone. It took me awhile to figure out what was wrong: I apparently had to play them on my MacBook Pro (and authorize myself with my username and password) before they would play on the iPhone.

Once I did that, at least, the process--finally!--worked flawlessly.

The major hitch isn't technological, because in truth the problems I listed above are more irksome than serious. The major hitch is Apple's decision to allow only songs purchased through the iTunes store to be converted to ringtones. It violates the principle of user supremacy: If you have an unprotected music file on your computer or handheld device, there should be no artificial limits imposed by unwilling software on what you can do with it.

The only explanation I can think of is that the record labels that sell through the iTunes Store have won this concession from Apple. ("If you want to sell our songs, you'd better not let MP3 files be used as ringtones...") I'd imagine that kind of pressure also explains why the iPhone doesn't include a handy file browser that would let you beam any file--including MP3s--to another iPhone user wirelessly.

So if I'm right, it makes some sense for Apple to comply. The bigger problem is that iPhone users right now are buying not just today's product but the promise of future software improvements based on the premise that Apple will continue to have their best interests in mind. This was that premise's first test.