iCal or iHAL? Apple and the Terrible, Horrible, No Good, Very Bad Day

Dear Mom:

You asked me to write to let you know if I arrived safely in iCloud-land. Well, I’m here and I’m in one piece, although unfortunately some of my things didn’t make it here with me, such as my calendar. It was a pretty hellish journey, I’ll tell you. There were a couple of long stops where I wasn’t sure I was going to make it the rest of the way, and we almost crashed a couple of times. The whole trip took about 16 hours! I think you’ll like it here in iCloud-land and I hope to see you here soon. But I hope you can find a less hectic day to travel.

Love, Wade

If I had to write a postcard home about my experiences switching over to iOS 5 and iCloud on Wednesday, that would the sanitized version. The honest version would include a lot more swear words.

Don’t get me wrong—the new version of Apple’s mobile operating system and the cloud-based sharing service that goes along with it are great. They make your iPhone, iPad, and Mac even more useful than they were before. If you’re an Apple customer who hasn’t already upgraded, I don’t want to discourage you from doing so. But I do want to summarize my tale of iCloud and iCal woe, in the hope of saving you a little heartache along the way.

Some of this story came out yesterday in an article in Talking Points Memo. Tech reporter Sarah Lai Stirland had come across the series of increasingly ticked-off tweets that I penned Wednesday as I attempted to get my whole menagerie of Apple devices upgraded to the latest specs. She called me up Thursday morning to ask for more of my tale, and I gave her an earful.

The new iCloud settings menu on the iPhone

But looking back on my tweets and my talk with Stirland, I regret playing the indignant card, because the truth is that I predicted all of this months ago, and, at least to some extent, brought it on myself. (I honestly only blame Apple a little—more on that below.)

I figured it was the duty of every self-respecting alpha geek to download iOS 5 the moment it was available Wednesday morning. Unfortunately, tens of millions of other iPhone, iPad, and iPod Touch owners were doing the same thing at the same time. So that was problem number one—the parts of the upgrade process that depended on Apple’s servers went in fits and starts.

The first order of business was to upgrade Lion, the operating system on my MacBook Pro, to the latest iCloud-compatible version (10.7.2) and to upgrade iTunes, long the master program in the Apple universe, to version 10.5. That all went fine. Next came my iPhone 4. That’s where the snags started, for me and a lot of other folks. Before iTunes can put iOS 5 on your iPhone, iPad, or iPod touch, it has to back up key data such as contacts and calendar appointments and completely erase the device itself, including all of your music, movies, books, and other media. Then it installs iOS 5, restores the data from the backup, restarts the device, and re-syncs your media material from iTunes. The restore part is what kept failing for me. The restore process would appear to be on the verge of finishing, but then it would fail, giving me cryptic messages like … Next Page »

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Wade Roush is a contributing editor at Xconomy. Follow @wroush

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