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

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“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 … Next Page »

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

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