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

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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.

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

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