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The Great iTunes Match Runaround

As you read in yesterday’s column, I’ve been unable to activate iTunes Match on an iPhone 4, running iOS 5.0.1. Each time I try to switch it on under the Music settings, I’m warned that “This Device Is Already Associated With an Apple ID.” I’m warned that I can only change Apple IDs once every 90 days, and when I click the OK button on the prompt, I’m taken to a browser window within the App Store, where the function to “Add This Computer” won’t accept a tap.

Now the message implies that I’ve used a different Apple ID for that iPhone within that 90 day window. Evidently this is a hard-coded block put there by Apple to — what? — keep you from accidentally or deliberately using your iOS device with different Apple IDs? Surely that can’t be the only reason.

For me, this complicated situation began with a request for help from Apple’s Express Lane chat support center, which is available for iCloud users. I had run into that “Already Associated” block when I first tried to use iTunes Match on my iPhone. The support person returned me to the Mac, where I was asked to remove my iCloud username, which was simply the original MobileMe account ID, and enter my iTunes Apple ID instead. Understand that the latter ID was established years ago, and has been used for all my Apple gear.

In turn, the 40GB online storage — a bone, evidently, offered to paid MobileMe subscribers — shrunk to the standard allotment of 5GB. And, no, there’s no way to transfer the storage, or, as I said, combine the accounts. Some time back, Apple CEO Tim Cook said the company was looking into the problem, but evidently they have to do a lot more looking before a solution is at hand.

Anyway, it turned out that my 2009 iMac, 2010 17-inch MacBook Pro, and an iPad 2, were all set up with my iTunes ID, and thus were able to retrieve my cloud-based music. That’s the good part. But the iPhone still hit me with that inscrutable message whenever I tried to activate iTunes Match. Indeed, the message frequently repeated itself simply by unlocking the iPhone and clicking on any app, including Mail, which had to access an Apple account of one sort or another.

My subsequent efforts to straighten things out resulted in several support hand-offs. iCloud support said go to iTunes, which only offers email help if you can’t find any relief in Apple’s online document collection. In turn, iTunes support said go back to iCloud, so I set up yet another Express Lane chat. There I was told the iTunes people got it wrong, but they evidently got someone from that department on the line to assist further. Between chat sessions, and awaiting iTunes email responses, I had used the Reset and Restore feature to clean things up on the iPhone without success.

Are you with me so far? It is exhausting.

The iCloud support person’s solution was to ask me to call Apple for help. Once phone support was alerted to my problem, they agreed not to exact a $49 fee for support (that particular iPhone doesn’t have AppleCare). Their solution involved doing a “full” Restore, meaning that I would be basically setting up the thing from scratch, without using a backup from which to gather old settings and apps.

The upshot? Well, after undergoing this entire process, I set up the unit for my Apple ID, and iCloud, with fingers crossed. Once again, the dreaded message reared its ugly head, this time because, for some reason, the newly wiped iPhone 4 “thought” that it had been set up with my MobileMe ID. The Apple rep said that, if nothing changed, I’d have to wait the required 90 period to set things right.

Now willing to take no for an answer, I wrote to iTunes support yet again, demanding a solution, since the Apple ID mixup on the iPhone occurred as the result of following their advice, not as the result of my attempts to troubleshoot. Within a few hours, I was assured that the iPhone had been removed as a device on my accounts, though I suspect they forgot that I had two, as you’ll see shortly.

Not willing to take chances, I did yet another Restore, though this time I used a recent backup so I wouldn’t have to endure another complete setup process. At the same time, I rejoined iCloud with my iTunes ID.

Now came the acid test, as I attempted to link the iPhone to the iTunes Match account. As you might have guessed, there was no change whatever. The problem was still there. I checked the MobileMe ID, and no devices were associated with it, so I’m back at square one, hoping Apple will devise a workable solution in my lifetime.

Meantime, that other iTunes Match defect I encountered, in which a small number of songs from an imported album weren’t matched while most were, is nothing unusual. I’ve done a little checking, and it appears this symptom is not at all unusual. Evidently the iTunes Match database needs some work, but I do hope the Update iTunes Match feature in iTunes will be sufficient to fix the problem once everything is working properly. I hate to think one might have to remove and re-add a music library from scratch to set things right.

But that’s enough for today. I definitely need some rest.