No it doesn’t Steve, wherever you may be.
Caveat lector. This is posted as therapy for me. You probably don’t want to read it.
What doesn’t work is the Apple ID. It has caused me more frustration in the past month than you can imagine — and while I am occasionally obtuse, I remain, like Yogi Bear, smarter than the average.
Here, as concisely as I can explain it, is what has happened.
I began eight years ago with one Apple ID (October 31, 2003, to purchase Peter Malick’s album New York City featuring Norah Jones). Through 500+ iTunes tracks, a few movies, and a few hundred apps I continued to use this ID, let’s call it NMK. (This is not the actual ID.) All my Apple devices (two iMacs, a MacBook Pro, my first two iPhones, an iPad, two iPods and two Apple TVs) are registered with this Apple ID.
In 2008 I purchased MobileMe, Apple’s email/syncing/online storage service. MobileMe required that my Apple ID have an email suffix (@mac.com or @me.com, they are interchangeable). Unbeknownst to me, that turned my Apple ID into two Apple IDs. Let’s call the second one NMK @mac.com (but that is not actually it).

Which was OK. I didn’t even know except every once in a while I would sign into email with my first, the store ID (NMK) and get rejected, or sign into the store with my email ID (NMK with the @mac.com) and get rejected. I, alas, never gave it much thought, just changed the ID thinking the sign-in requirements were different, not that I was dealing with two different IDs. After all the unique ID part was the same for both! The password was the same for both! The credit card was the same for both!
Until iOS 5 and iCloud last month.
I had a helluva time getting it to work until I finally realized I had two different Apple IDs — and it took me two frustrating days to realize that. Ultimately I learned to sign up to the store with the first and to iCloud with the second. Everything seemed to work, though my OCD caused me to twitch. [I bought an iPhone 4S last month. I see now that I registered it to the second account, unlike every other Apple device I own.]
Then this week, iTunesMatch became available — for $24.99 a year it matches your iTunes library in the cloud so that all of your music is available to all of your devices. Very nice. (It does seem to work reasonably well.)
I subscribed to iTunesMatch Monday without thinking about which ID I was using. And I used the second, the iCloud ID. The one where I have only one device. The one where I own no iTunes music or movies. The one where I cannot update my apps. The one I don’t use with my Apple TVs for Home Sharing.
So, this week, by telephone or email, I have dealt with four different Apple customer service reps to correct my mistake. As Apple claims to be unable to merge Apple IDs (WTF?) or to transfer purchases between IDs, I suggested they refund my iTunesMatch subscription and let me start over with the correct Apple ID. A little while ago this is what I was told:
“With that in mind, I consulted two supervisory agents to seek assistance and a possible refund. Ken, I am truly sorry, both have let me know that because of the nature of iTunesMatch, we do not have the option to provide a refund. If I could make this right I certainly would.”
Apple’s solution is to log in and out of the two IDs depending on whether I want to update purchases or listen to the music in the cloud. “[Y]ou can manually manage your devices and content and enjoy purchases from both accounts.
Manually manage! Manually!? WTF?
(This is even stupider than it sounds. When I sign into the store to buy or update an app for example, all of the iTunesMatch data disappears. And, as I have thousands of tracks, it takes considerable time to reload it on any of my exclusively Apple devices.)
So, it doesn’t just work then, does it?