If you’re a regular reader of these columns, you know that I’ve had a love/hate relationship with iTunes and how it interacts not just with my various online purchases, but with my Macs and iPhone 4s. A key example is iTunes Match, which, in exchange for $24.99 per year, will match your music library with equivalents in the massive iTunes library. Well mostly anyway.

Although some of you don’t think it’s very important, I’ve noticed that one or more songs from a ripped CD of an album also available in iTunes, often won’t be matched. iTunes support has never been able to explain why, other than to give me boilerplate responses about how the iTunes Match system works.

Most recently, I ran into yet another curious problem, after buying a newly released album from iTunes, “The Best of Pink Floyd: A Foot in the Door.” This came from a special “Mastered for iTunes” collection, where the tracks are, according to Apple, “specially tuned for higher fidelity sound on your computer, stereo and all Apple devices.” Clearly they are trying to get as much quality as they can from a 256K AAC digital file.

Well, this purchase seemed trivial enough, except that track three, “The Happiest Days of Our Lives,” wouldn’t download. I kept getting a prompt that the song was corrupted. After putting up with this grief for a day or so, and not faring any better in retrieving a pristine copy of that file, I contacted iTunes support, which promises to respond within 24 hours via email.

That’s where my adventures began.

Over the next couple of weeks, I kept getting the same responses, where they forwarded me to a few Apple FAQ documents that basically covered all the steps I’d already taken, but those steps never solved the problem. Since I was entitled to phone support as the result of my recent purchase of an iPhone 4s — and I also encountered problems trying to retrieve the track from that device too — I called up Apple. With the help of level one and level two support, I went through everything all over again. Finally I was informed that the people who manage the iTunes Store operations would take over the case, even though I was allegedly the only one to report a problem retrieving that file.

A few days later, I was able to retrieve an intact file to complete my album. But with all the credits Apple gave me for my trouble, it cost me nearly nothing to put up with all that nonsense. Maybe I should have just bought a copy from the nearby Walmart superstore. Live and learn, but I gather I’m not the only one to encounter corrupted files from the massive iTunes library.

The next oddity is with the iPhone 4s itself. It took interaction with Apple to help me configure a ringtone from iTunes (“Hello Goodbye” by The Beatles) as a default. It originally worked for two days, then the ringtone disappeared. Downloading the file again failed to place it among available ringtones, even though I tapped the option to make it the phone’s default. It took two restores to set things right; the second attempt involved setting up my iPhone as a new device, rather than using a backup. This also meant that I had to spend a little time redoing all my settings, but the effort got me the ringtone. It probably wasn’t worth it.

In recent days, I have also confronted “the case of the repeating login prompt.” Every few hours, I get a notice on the iPhone asking me to reenter my Apple ID password. Now you will get such messages when buying something from iTunes or the App Store, and whenever you download an app update. But this ghost-like request doesn’t coincide with the usual tasks that normally generate such a message. It just happens, with neither rhyme nor reason.

Well, that’s one symptom that Apple is still investigating. The problem arrived with the setup of the iPhone 4s, survived restores, upgrades to iTunes and installation of the iOS 5.1 upgrade. No change.

But, of course, the entire Apple ID scheme is broken. Many of you are forced to use more than one, particularly if you’ve attempted to migrate a MobileMe account to iCloud, yet you already have an Apple ID that you use for your iTunes account and purchases of Apple gear. Without judicious adjustments of the sync settings on your Mac, iPhone and iPad, you may find that your contacts, for example, are different from device to device. Even trial and error may fail to resolve the “contact list from hell” problem. Worse, Apple still has no way to let you merge all your accounts, and I’m lucky to have just two.

Now I understand why some of you have several Apple IDs, and it’s not just for business purposes, or to separate purchases among family members. You may just forget your Apple ID, so you create another when setting up a new product. Soon things get a little complicated, particularly when you try to manage an iTunes library with content purchased from different accounts. iCloud was meant as a great unifier, but it remains crippled so long as you have some stuff in one Apple ID, and other stuff in another.

Yes, it’s good to know that over 100 million Apple customers are using iCloud. But wouldn’t it be nice if Apple fixed the Apple ID problem so the system works as it should?

This article was posted on Friday, March 23rd, 2012 at 12:00 AM and is filed under News and tagged with: App Store, Apple, Apple Id, iCloud, iOS, iOS 5.1, Iphone, iPhone 4S, Itunes, Macintosh, MobileMe, Pink Floyd.