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What is Palm up to? With its new WebOS 1.21 update, it’s once again renabled the Palm Pre’s ability to sync unprotected music and videos, photos, and now photo albums with iTunes, no extra software required. The move comes after the USB Implements Forum took Apple’s side in the tiff over Palm’s spoofing of iTunes into thinking that the Pre is an iPod. If I recall correctly, Apple has released two iTunes updates that blocked earlier versions of WebOS from syncing, and chances are presumably sky-high that it’ll block this one the next time that it pushes out a new version of iTunes.

I keep declaring this clash of wills between the two smartphone companies to be over, but I’m officially giving up on making any guesses. Whatever will happen will happen, and Palm, at least, isn’t behaving in the nice, predictable way that you expect of large companies. I dunno how the USB-IF will respond to Palm ignoring its stance that the Pre shouldn’t masquerade as an Apple product via USB connection, but it seems to be clear that Palm is willing to burn bridges behind it.

The company is unquestionably bursting at the seams with smart, talented folks; the Pre remains the iPhone’s most formidable competitor by far from the standpoint of user-interface sophistication. But I’m mystified by what it’s up to here. Palm continues to tout iTunes compatibility as a major feature of the phone. But the convenience that the feature offers when it’s working is completely negated by the periods when it’s in limbo, not to mention the general uncertainty of the whole idea. Whether you take Apple’s side or Palm’s or (like me) aren’t completely thrilled with either company’s behavior, it would be silly to think of the WebOS’s Media Sync feature as an argument in favor of buying a Pre.

Mac and iPhone developer Craig Hunter has a cogent post up on all this that beats up Palm pretty good. He wonders the same thing that I’ve been curious about for months: Why doesn’t Palm, like numerous other companies, write a standalone app to do the syncing? It would work well, and there’s no evidence that Apple would try to foil it.  Just how many Pre owners would vote for continuing to play chicken with Apple when there’s a boring but effective alternative route to nearly the same end result?

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New development in the ongoing saga of the Palm Pre’s Media Sync feature, which has let Pre owners sync directly with iTunes by tricking iTunes into thinking the Pre is an iPod: Palm’s attempt to get the USB Implementers’ Forum to intervene has failed. All Things Digital’s John Paczkowski is reporting that the USB-IF has told Palm that the Pre’s masquerade seems to violate the organization’s policy, which is that a manufacturer can only use the USB IDs it’s been assigned. (Palm has been using one assigned to Apple.)

This is not a startling development: I woulda put ten-to-one odds on it happening all along. The Pre has pretty much been using somebody else’s driver’s license to get into a bar–or, if you prefer, somebody else’s invitation to get into a party.

What’s Palm’s next move? I keep thinking that it’s got no options left but to surrender, but who knows? I do notice that the Palm site still touts Media Sync:

Here’s the footnote:

No matter how you slice it, this is misleading and out of date: We already know that iTunes 9 breaks Media Sync, so whether or not Palm “guarantees” compatibility is irrelevant. And iTunes 9 isn’t a future version, it’s the current one. I guess “Plus, use the Palm media sync feature to transfer your DRM-free iTunes music, video, and photos to your Pre…as long as you’re using an old cersion of iTunes” doesn’t have the same ring to it.

I wanted Palm to win this fight, and I think everyone, including Apple, would win if it iTunes had some level of built-in support for non-Apple devices. But it’s surely time for Palm to either eliminate references to media sync as a selling point or introduce a Media Sync 2.0 that uses a bit of middleware to do the syncing, a technique which works just fine. If I’d bought a Pre in part because Palm told me I’d be able to sync with iTunes, I know I’d vote for the latter option…

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When Steve Jobs was detailing the wonders of iTunes 9 at yesterday’s Apple music event, there was a One More Thing he didn’t mention: The new version of the software once again blocks Palm’s Pre from making like an iPod and syncing music and video directly with iTunes. This is the second time that an iTunes update has foiled the Pre. (Palm responded to the first attempt by using a workaround to regain access to iTunes.) And even if Palm has another kludge up its sleeve, it should bring this saga to an end.

I say that with regret, because I was rooting for Palm: iTunes sync is a nifty feature, and I wish that Apple looked at non-Apple phones syncing with iTunes not as an intrusion, but as an opportunity to sell more music. (If it did, it might actively court other phone manufacturers such as Palm.) But we now know that Apple won’t even take a laissez-faire approach here–it’ll boot the Pre out again and again.

Which means that it’s silly for Palm to promote the Pre’s Media Sync feature as it stands as a reason to buy the phone–even in a best-case scenario, the feature is doomed to an unhappy, tentative future.

The solution seems simple to me: Rather than hacking iTunes to provide direct syncing, Palm should use a bit of PC/OS X middleware to do the job. Lots of products do this without controversy, and Palm can probably license the technology if it needs to. In theory, it’s not as elegant a solution as direct syncing, but it works. And there’s absolutely nothing elegant about the cat-and-mouse game that Media Sync has been playing with Apple to date.

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