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The iCloud Report: Did I Say Cloudy?

With over one week’s experience with iCloud under my belt, so to speak, I am somewhat underwhelmed with the way it works. I mean, it’s good to see Apple trying over and over again to find the road to success in building some sort of online service portfolio, but previous efforts have been hit and miss, and miss was often the operative term.

As I wrote awhile back, Apple got into the online game back in the 1980s with a service for dealers and repairers known as AppleLink. A consumer-based version was abandoned, but Apple’s partner in that venture used it as the basis for America Online. In the 1990s, Apple tried eWorld, using AOL’s technology, and gave it up after failing to provide a suitable alternative to AOL. For the 21st century, we went from iTools, to .Mac, MobileMe, and now to iCloud.

Are we there yet?

Certainly if the October 12th rollout is an example, the answer would be a big fat no, but you cannot take the initial rollout, which coincided with the release of iOS 5, Mac OS 10.7.2, and other goodies, as an example of a depressing trend. On that day and the next, my mac.com (or me.com) email worked in fits and starts.

But the real problem for me occurred in the days that followed, where regular email notices from our Web server would be unceremoniously deposited in the Junk mailbox. I turned off Junk filtering in Lion Mail with the same result, at Apple’s urging. No change. Even though I continued to flag the messages as Not Junk in the iCloud.com email reader, the messages were still regarded as spam. Worse, the problem was never consistent, and the email messages from our backup server seemed to get through without incident.

As I write this column, Apple is suggesting that, if the problem doesn’t go away, I give them permission to examine my account and see if they can find a cause. To do that, of course, I have to prove to Apple that I am the actual account holder, and provide them several tidbits of information to confirm my identity, but I’m still deciding whether to take that route.

Aside from the growing pains, Apple’s biggest problem is probably related to those notorious Apple IDs. iCloud expects you to have one, but many Apple customers have several, distributed among family members, and perhaps to separate the home and business accounts. In my case, I have the same Apple ID I set up years ago when iTunes debuted, plus one for the .Mac and MobileMe subscription plan that has lasted all these years.

What this means, of course, is that services on other accounts, such as my iTunes music library, aren’t going to integrate with my iCloud email, document storage, and so forth and so on. This has to be thoroughly confusing, and since Apple has tens upon tens of millions of accounts, they have a bear of a problem to confront. Already two reports, quoting Apple CEO Tim Cook, make it clear they are working on a solution. To me, the solution would be to allow you to integrate all of your Apple IDs into just one, if that’s what you want, after somehow proving to Apple that you are the one and only holder of all those accounts. Indeed, I suppose that’s a significant problem that has to be resolved in a consumer friendly fashion.

My other concern is how Apple will address the curious situation where Mac users who haven’t upgraded to Lion are getting shafted by not being able to use iCloud, while Windows users running Vista or Windows 7, courtesy of an iCloud control panel, can use the service. Is that fair? Now it’s true that Apple made serious revisions to Address Book and iCal, two linchpins of iCloud, which may require extra work to resolve. Perhaps Apple could update those two apps in a special update for Leopard and Snow Leopard users. Regardless of the solution, Mac users deserve to be able to set up, or migrate to, iCloud even if they won’t or can’t update to Lion.

I hear rumors that a solution is being worked on. I hope it arrives soon, assuming those of you who are on older versions of the Mac OS care. But if you’re a MobileMe user, you should, since that service goes away as of the summer of 2012.

The other concern is that Apple dropped several integration or sync features in transitioning from MobileMe to iCloud, such as the ability to match up your keychains, Mail preferences, Dashboard widgets and other settings. True, each and every one of these features were flaky, at least from my experience. Perhaps they will be added if and when Apple devises better solutions.

For me, aside from the email glitches, iCloud has worked all right. But I won’t be able to use it fully until there is a solution to the case of the multiple Apple IDs. I hope that solution arrives soon, just as I hope iCloud won’t become something else in a year or two. I’d like to see Apple get this one right, or it will begin to sound like the sort of stunt Microsoft pulls with underperforming products and services.