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 “The iPhone ‘iPhone’ could not be restored. An internal error occurred,” or “Error 3401,” or “Error 3200.” According to an Apple support page, Error 3200 indicates a “network-connectivity or traffic issue” and the resolution is to “wait an hour or more and try again.” That’s what I did—about eight times, until the process finally completed. Meanwhile, my iPhone was a brick.

Once it had been brought back to life, though, I was emboldened to go through the same process with my iPad 2. This time, the restore process worked on the first try. The only slowdown was syncing all my apps and media back to the device—I have a 64-gigabyte iPad and it’s about 70 percent full, so that process took a couple of hours. (I recommend that you have some homework or reading at hand when you start this whole upgrade process. I had an overdue profile of San Francisco startup Yammer to work on.)

Next I was eager to explore iCloud. This isn’t something you install—you just activate it from your computer and your devices and tell it what sorts of data you’d like it to automatically sync across all of your Apple gadgets: mail, contacts, calendars, reminders, bookmarks, notes, photos, documents, et cetera. I wanted to test photo sharing first, but I immediately ran into my next hurdle. To use Photo Stream, Apple’s new system for copying photos across your devices, you need the newest version of iPhoto on your Mac—it’s called iPhoto 9.2. But I was stuck on version 9.1.5, and 9.1.5 didn’t seem to know that an upgrade was available, or that 9.2 even existed. I had to dig it up on Apple’s website (it’s here) and download and install it manually. (Don’t make the mistake of buying it from the Mac App Store, where it costs $14.99.)

Anyway, the manual download did the trick—Photo Stream is now working great for me. Photos that I take on my iPhone or iPad show up immediately on my Mac, and I can even browse them on my big-screen television via my Apple TV (now that it, too, has gotten a software upgrade). It’s pretty amazing.

Next: iCloud and calendars. This was the low point of my day, and this is the part of the story that does not have a happy ending. In truth, I should have been ready for trouble. For about four years—ever since buying my first iPhone in 2007—I’ve been using iCal as my main datebook program, and within iCal, I’ve long had three separate calendars, one for work, one for home, and one for events imported from Google Calendar. Back in June, when I got a new MacBook Pro and tried to sync it with my older iPad and iPhone, I wound up with two copies of every iCal appointment. I could never figure out why, and I had to delete all the extra copies manually.

I suspected then that Apple doesn’t really understand calendars or how to synchronize them across devices; it was precisely the same issue with duplicate calendar appointments that had caused me to ditch Apple’s widely derided MobileMe service a couple of years earlier.

But I had no idea how bad the problem could get. As soon as I activated iCloud on my iPad, iPhone, and Mac, a mindless cycle of duplication began: soon I had four copies of every appointment, then six. And it wasn’t just the individual appointments that were getting duplicated: it was whole calendars. At one point iCloud had created 22 separate calendars—10 copies of my home calendar, 10 copies of my work calendar, the Google calendar, and a master iCloud calendar.

While the calendars were multiplying, iCal itself kept crashing on my Mac, trying to restart itself, and crashing again, then restarting again. I wasn’t able to interrupt this cycle, and it made using the machine impossible, as the new iCal windows would keep appearing on top of my other windows. When iCal crashed, it was showing a message about network errors, so I finally turned off the Mac’s Wi-Fi connection, which stopped the crashes.

Then I had to decide what to do about all the duplicate appointments. In my defense, it was late (around midnight), and I was weary from a day in the technology trenches, so I probably wasn’t thinking straight. I figured the best thing to do would be to delete all of the calendars from all of the devices, then restore iCal on the Mac from the archive file I’d made earlier, then let those old appointments propagate back to the iPad and iPhone.

So that’s what I tried. And the plan would have worked, if the archive had been intact—but it turned out it wasn’t. Either it hadn’t been saved correctly or it had been corrupted, and there was nothing in it.

At this point, Apple experts are probably saying “What about Time Machine or Carbonite or Mozy? Don’t you have a backup of your calendar somewhere?” Perfectly reasonable questions, but this was a bit of a perfect-storm moment for me. My old Western Digital Time Machine drive failed recently, and the new Seagate one isn’t working right, so I had no local backup. I activated the Carbonite cloud service on my MacBook when I got the machine in July, but it hasn’t finished its first full backup yet, and the calendar is one of the items it hasn’t gotten to.

So my calendar was truly empty—except that it isn’t; I have a slew of interviews, conferences, and trips coming up over the next three months. So I stayed up very late Wednesday night going through my e-mail archive on Gmail in an effort to reconstruct my schedule. I think I’ve got most of it back, but I already missed one overlooked appointment on Thursday, and there are bound to be more. Please, if you’re reading this and we have an appointment to meet at some point in the future, e-mail me now at wroush@xconomy.com to confirm.

If there’s a lesson in my calendar catastrophe, it’s that you should never delete all of your calendars, and that you should make sure you have an intact, usable copy of your iCal archive (and everything else) stored away before you start any of these upgrades. It’s my own damn fault that I didn’t have the proper backups. But it’s Apple’s fault that its iCloud network connectivity problems on Wednesday caused iCal to fail so ungracefully. (If anyone can explain why the duplicate calendars were being generated in the first place, I’d be very grateful. I suspect iCal would have gone on creating extra calendars forever unless I’d essentially disconnected its brain by cutting off the Wi-Fi. Perhaps Apple should rename the program “iHAL.”)

Everything seems to be working fine now. New calendar appointments and contacts get synchronized quickly and accurately across my three machines. I love all the other new features of iOS 5, like the notification center, the instant access to the camera from the iPhone’s lock screen, and the tabbed browsing and “reader” features in the Safari Web browser. But most of all, I love the idea that Apple calls “PC Free.” This is a philosophy and a policy rather than an actual feature or an app. It means that in principle, you’ll never have to go through iTunes again to back up, upgrade, or restore your iPhone, iPad, or iPod touch; thanks to iCloud, all of that will happen automatically and wirelessly. I hope it really works out that way, because for me, never would be too soon.

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

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