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 freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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14 responses to “iCal or iHAL? Apple and the Terrible, Horrible, No Good, Very Bad Day”

  1. Jered Floyd says:

    Thanks for the warnings. I’ve found that Apple’s calendar management has always been sub-par, so I just use iCal and my phone as CalDAV clients to Zimbra. Guess that’s not going to change.

    I had a question about a throwaway item you mention, “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[…]”. July was 3 months ago. Is Carbonite that slow, or have you just not left your laptop on for it to do its work?

  2. welcome to the 21st century says:

    PC-Free – welcome to the 21st century. My Android Motorola Photon 4G is PC Free, my Blackberry was PC Free and wires free, My Palm Pre was’nt just PC Free, it was wires free since I charged it through the touchstone charger and moved everything on and off through wifi. Glad to see Apple joining the rest of the crowd.

  3. Howard Simson says:

    The theme of this article could be summed up as “Apple software really failed, but I blame myself.” I am a Windows user, but also an owner and user of Apple products. While I love Apple design, workmanship, and mobile devices software design, I have always been frustrated with the Mac software implementation and platform. Under Windows, if something like the scenario detailed in this article happened, I expect I would have enough avenues to pursue (if needed, behind the scenes in temp directories etc.) to rectify the issue, or at least locate a backup before it got wiped out.

    I can’t help but wonder if the author and other Apple users would rather blame themselves for Apple failures, because admitting anything contrary is akin to “treason.” The author said it was a terrible, horrible, very bad DAY. To me, it seems a terrible, very bad implementation of SOFTWARE. Mac (and Apple) fans continually trumpet Apple platorms as so much easier to use, and less likely to fail, crash, or destroy data. I appreciate the author detailing what happened to him, but he didn’t have to (repeatedly) take ownership for the failure. That belongs to Apple.

  4. Wade RoushWade Roush says:

    Jered — Yes, I’m also a little puzzled about why it’s taking so long for Carbonite to finish backing up my MacBook. I do turn the laptop off every night from roughly 11 pm to 7 am; perhaps I should just leave it running until it finishes. Or perhaps I should investigate and find out if the backup is stuck for some reason.

    Howard — I think you have a good point. I’m generally happy with my Apple devices, which, overall, seem a lot more user-friendly than what you get in the Windows world. Balanced against that, however, all Apple users have to go through these periodic, incredibly painful upgrades & adjustments where, in the end, it’s Apple’s way or the highway. And those are system implementation shortcomings, as you say. We probably don’t complain about that enough.

  5. Brian says:

    I’ve been warning everyone I know across all platforms – not just Apple – to be very wary of “the cloud”. It’s a great idea to be able to store things remotely and access them on the fly – but it is a horrible idea if people don’t think to keep a copy of that data themselves, whether saved on their hard drive, burned on a disk, thumb drive, or even the old fashioned thing known as “writing it down”.

    While the calendar incident you describe is, as you described it, a kind of “perfect storm” of events that led to your data loss, for a lot of people, making backups of data is just not something they think about.

    Those people will learn the hard way when they go to pull up their data from “the cloud” for a business meeting or presentation and are confronted with the server being too congested… or down… or their data being corrupted… or any of the other bajillion things that could (and for some unfortunate users WILL) go wrong.

    As much as I love gadgets and technology, I’ll never get rid of my good old fashioned paper planner calendar that I carry with me. It’s OS has never crashed once.

  6. Greg R. says:

    Hello Wade,

    I have to smile with you. You must have been in my office at the same time; I worked “ALNIGHT” with iOS 5 and the iCloud it was fun to a point, “Like what do I want to try first”…. Anyway after a long day in academia (working with students), I started the “Download” (one of the “tens of millions”) I was also watching MLB NLCS “Go-Cards”….. Good Game still downloading 3hours+ after the iPhone was done; it was time for the iPad2, now it is going on 3am CST. So to make the long too short of it, I do have a lot of calendar now and I will read what others are doing to fix it while I wait on my New “Back Ordered” iPhone 4S (that I order in the at&t store on October 7th at 3pm CST)…. Good Luck Let me know how it goes :-)and a good store too!

    Greg R.

  7. sam says:

    Can you imagine the same traffic or more congested next time around since everyone upgrades their iPhone, iPad… at the same time with PC-free iCloud? If Apple does not figure out a better way by then, PC will be back.

  8. Jered Floyd says:


    Let me know what you find (or maybe your post will prompt Carbonite to repond); 3 months to first backup doesn’t sound like a useful product to me. I hope they aren’t charging you!

    My iPhone 4S just arrived, but I’m unable to activate it. Not too surprising, as that’s been the case every year on launch day. It seems to be a problem isolated to AT&T — you’d think they’d have learn to expect it by now. I’m sure the back-end provisioning systems are some rusty boat anchors running some monstrously over-complex BPM software….

  9. Brian says:

    Jared – actually its on Apples end, not AT&Ts. Apples system is down nationwide. Our local Apple store cannot even sell their phones and is now taking names from customers in line. Hopefully they at least managed to get the antenna right this time!

  10. Jerry says:

    Wish I had read this before I tried. My problem (really? Blaming myself?) was that my iPhone was connected to my laptop, and synched to it and to iCloud, duplicating by calendar. I turned off synching to my laptop (thru iTunes), and now only have one set- but really shouldn’t the software have recognized this?

    The really frustrating part was that I couldn’t find any help for my problem on the Apple site. I guess since it “just works” they don’t have to provide help.

    I noticed in your screen shot, you hadn’t turned on mail in iCloud. I haven’t been able to figure this out either. Do I have to stop using my current email address (not going to happen) and only use the .me account to have my mail synch both directions? Again, where is Apple’s help?

    I’m one of those devoted Apple users, but this time…. GRRRR!!!

  11. Wade RoushWade Roush says:

    Jered: I consulted with Carbonite. Here’s their response. As I suspected, the fact that I’m turning off the laptop every night is slowing down the backup:

    “Hello and thank you for contacting Carbonite Customer Support.

    We are sorry for any inconvenience this may have caused you. We have reviewed your account and see that the backup is progressing normally when your computer is connected to the internet. You have good internet upload speed as well. You are correct that turning the computer off at night is causing the delay in completing the initial backup. If you can leave it on as much as possible just until the initial backup is finished it would speed up the process considerably.

    Also, when your computer enters hibernation/sleep mode, your internet connection is interrupted, effectively stopping the progress of your backup or restore. To adjust your hibernate and sleep settings on a Mac, you can use Energy Saver. For more details, please click the link below.

    Hibernation and Sleep Mode: http://carbonite.custhelp.com/app/answers/detail/a_id/1488

    Please let us know if you need additional assistance.


    Carbonite Customer Support”

  12. Ben Lowengard says:

    It’s terrible when an update failure happens to a blogger. As someone who has done quite a few updates to iCloud I offer this advice:
    Backup (good) Contacts and calendars before updating.
    Check to see if you have enough ram (1 gig just does not cut it on a MacBook Pro)
    Update all devices to Lion and IOS5 before switching to iCloud.Then go to Mobile Me and do the switch.
    Plug your IOS device directly into a USB port for the update esp iPads- you may want to turn off Sleep (on your main computer) as well.
    Caveats may happen, but generally it works well. This is a sea-change in how you update things with Apple- you have to pay a little more attention. Snow Leopard will have to change mail settings to the iCloud servers (if you need to use SL).