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Palm, Apple Continue iTunes-Syncing Battle

Late Thursday, Palm released the 1.1 version of its Pre smartphone's WebOS operating system, and in so doing continued its thumb wrestling match with Apple over the Pre's ability to sync with Apple's iTunes software.

Palm broke the news in a cheeky blog post that reused a favorite phrase of Apple CEO Steve Jobs:

Oh, and one more thing: Palm webOS 1.1 re-enables Palm media sync. That's right -- you once again can have seamless access to your music, photos and videos from the current version of iTunes (8.2.1).

(WebOS 1.1 also includes a host of fixes and enhancements to its e-mail client, calendar, Web browser, to-do list and other programs, though none that cover the issues I noted in my review and accompanying blog post.)

So once again, Pre users can plug in their phones to a Mac or Windows computer, have their copy of iTunes recognize the Pre as an iPod, and synchronize multimedia as if it were an iPod. But to defeat the countermeasures Apple added when it shipped iTunes 8.2.1 (blandly described in Apple's minimal release notes as a fix for "an issue with verification of Apple devices"), Palm had to engage in a more thorough form of identity theft.

Earlier versions of WebOS would, essentially, identify the Pre as an iPod when you plugged it into a Mac or PC and selected the "Media Sync" option on the Pre's screen; the Pre would then show up in iTunes as an iPod manufactured by Palm, Inc., with a serial number like "XXXXXX." Now, apparently, it appears as an iPod made by Apple -- because Palm is appropriating Apple's USB vendor-ID code, something companies aren't supposed to do as a good USB citizen.

So now what? Apple will probably try to add some extra screening to the next version of iTunes to watch for this, after which Palm will respond by doing an even better job of impersonating an iPod. I'm not sure how Apple can win this competition -- as long as there are millions of older iPods in the market that the Pre can attempt to mimic, Apple risks causing compatibility problems for its paying customers if it gets too strict in its scrutiny of media players.

Meanwhile, Apple has a bit of a hypocrisy problem: The Mac version of iTunes explicitly supports some old, non-Apple music players, although none have been added to that list in years. Apple also allows third-party programs to synchronize other devices by reading your own iTunes files. Its stance appears to boil down to "you can sync any other player to iTunes as long as it's not too new or too easy to set up."

But that's Apple's right as a developer. I can also see how this company could feel threatened. The Pre doesn't amount to an iPod equivalent -- it doesn't show the one- to five-star ratings you can assign to songs in iTunes, doesn't offer as many ways to sort through a music collection and doesn't offer the elegant click-wheel controls of most iPods--but it can be a good-enough iPod alternative. Do those potentially lost sales outweigh the costs of playing a possibly infinite round of whack-a-mole with Palm's developers? Only Apple's accountants know for sure.

How would you like to see this dispute end? How do you think it will? Please note in the comments if you own or are thinking of buying a Pre.

By Rob Pegoraro  |  July 27, 2009; 10:57 AM ET
Categories:  Gadgets  
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As not being one who is up to date on iTunes, let me ask a few questions.

1. You can use iTunes to rip CD's to an mp3 player. Right? Why would Apple care about this? They GIVE the software away (free download).

2. You can use iTunes to BUY music from the Apple store. Right? Why would Apple want to cut this potential revenue stream?

Yes, the Pre is a competitor to the iPhone. But, is it really going to kill (or even seriously dent) the market that the iPhone has? There are thousands of applications for the iPhone that are not, and probably won't be, available for the Pre. People buy the iPhone BECAUSE its from Apple. They will tell their friends that they have an iPhone. I doubt that there will be much bragging about an imitation iPhone.

Any answers?

Posted by: blasher | July 27, 2009 11:26 AM | Report abuse

Apple is just being stupid. By now, every Palm Pre user knows not to update past a certain version of iTunes. So unless Apple remotely disables older versions of iTunes, only people who don't have the Pre (and thus don't care for the upgrade) will be bothered.

Posted by: tundey | July 27, 2009 12:39 PM | Report abuse

Apple has to at all costs avoid giving, even tacit, approval for the Pre to use it's iTunes software. Were it to, it would be obligated to do the same for Symbian phones, or heaven forbid, WinMobile junk too.

And yes, Pre users can stay with the old iTunes software. How nice it must be to live in a backward, upside down world of the Palm Pre.

I have no intention of buying a Palm Pre, I already experienced Palm's complete and utter complacency when I switched to an early Treo. And that's beside the obvious issue of poor quality.

Posted by: JonT1 | July 28, 2009 7:22 AM | Report abuse

I have a Palm Pre and have been very pleased with it.

It appears to me that Apple is engaging in the same monopoly practices to squeeze out competition it used to revile Microsoft for using. Apple should focus on making a superior product (and incidentally not straitjacketing people to AT&T) and less on trying to distort the market.

Posted by: jcbjackson | July 28, 2009 9:30 AM | Report abuse

I store my music on my computer to listen to it, and to sync to hopefully whatever mp3 player I chose to buy. The idea that I have to store and manage separate copies of my music, one for the computer and one for my cell phone/iPod/mp3 player, is ridiculous. The job gets more ridiculous when I think of the time and effort I put in to creating playlists and cover art and even getting lyrics for the music.

I don't want to have to manage what songs were bought through an Apple store and what were bought through a Pre or Amazon store. Especially in a world of DRM, where I still have to ask if it's legal to copy a music CD onto my computer.

I can somewhat appreciate the Apple position: They see themselves as a hardware company and believe their iTunes is the front end to the iPod. But I think it stopped being just that when they tied in a (great) music management system.

I've had a Palm treo for years and loved it. I wanted to upgrade to either an iPhone or Palm Pre. Unfortunately my company won't support either of those phones, so it's a blackberry for me. :-(

Posted by: tokrueger | July 28, 2009 10:50 AM | Report abuse

I have an iPod and do little with the music as I bought an iPod for a woman friend to give as a gift and I bought and downloaded a lot of music from the Apple Store. I then found out that because the music on the iPod wasn't bought from her computer that when she syncs up her iPod and her computer and tries to buy music from the Apple Store it will wipe out the music I bought for her. So much for me ever buying more music from the Apple Store. I also will not buy an iPhone since I don't want to be on AT&T. Since I use Sprint and am sticking with it, the Palm Pre is an option which I may buy but not yet. I'm basically waiting for the iPhone to be available for other carriers.

Posted by: rsrosenwald | July 28, 2009 11:00 AM | Report abuse


Assuming you put drm music from the iTunes Music Store on your friend's iPod, all you have to do is transfer that same music to iTunes on her computer (using, say, a USB Flashdrive or an external hard drive) and authorize her computer to play it by entering your iTunes store user id and password. You can authorize up to 5 computers per account. If it is not drm, then just transfer the music to iTunes on her computer, you don't need the password. In either case, once the music is in iTunes on her computer, it will not be erased when her iPod is synced to iTunes. iTunes will also add to her iPod any additional music she has purchased or otherwise added to iTunes.

Posted by: chevychase10 | July 28, 2009 12:33 PM | Report abuse


When I said "transfer," I meant "copy", assuming you want to keep the music on your computer as well.

Posted by: chevychase10 | July 28, 2009 12:37 PM | Report abuse

I think that Apple wouldn't have to worry about people buying competing phones if they hadn't locked themselves into their exclusivity agreement with AT&T. That's the number one reason why people I know say they don't/won't have an iPhone. They don't want to switch carriers or they just plain don't like AT&T.

Posted by: HollyTZ | July 28, 2009 1:05 PM | Report abuse

@blasher: Good point about expanding the reach of the iTunes Store. Apple doesn't make a huge amount of money off iTunes purchases, but it's still something.

@JonT1: No argument about Palm's history, but you should realize that the Pre has nothing in common with the Treo and the Centro besides a slightly similar keyboard layout.

@rsrosenwald: See chevychase10's reply for one way around this; these files, like any other file on your computer, can be copied at will from one computer to another. If they're in iTunes Plus format--as they should be if you bought them anytime after early April--there's no need to authorize your friend's computer with your iTunes account.

Another option your friend has is to use a program to copy the music from the iPod right to their computer, as outlined in this Help File item I wrote in 2007. (Since so many people seem unable to find this piece on their own, is it cool with everybody if I just re-run this item verbatim on a slow week in August?)

- RP

Posted by: Rob Pegoraro | July 28, 2009 2:29 PM | Report abuse

I am waiting on a Verizon Pre and have had earlier Palm phones. It's great to see this little game being played out just as long as Palm doesn't get hurt. It would be nice to hook up to iTunes I guess but I also have an iPod classic so it's not immediately necessary.

Posted by: gsdlea | July 28, 2009 8:23 PM | Report abuse

Apple is more interested in selling phones than it is in selling music. The latter is a means to the former end. They just need to decide if they want to sell music to people who DO NOT WANT an Apple hardware platform. If not, then there are other willing sellers (DRM free, too), even if their computer interface is not quite as elegant.

I would buy a Pre tomorrow if I could get it from Verizon Wireless and it had a memory expansion slot.

Posted by: 54Stratocaster | July 28, 2009 10:04 PM | Report abuse

If Apple quits playing Whack-A-Mole, it risks all manufacturers interacting with iTunes, and breaking its monopoly there. The competitive phones aren't the biggest risk, it's otherwise non-competitive MP3 players.

Posted by: alexburns5202 | July 30, 2009 9:20 PM | Report abuse

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