Hold off upgrading MobileMe iCal

No data in the calendar.

UNLESS YOU ENJOY waking up to a blank calendar, hold off upgrading MobileMe iCal for now. Prior to the latest update, I enjoyed flawless, seamless calendar integration across my desktop and laptop computers, iPhone, and iPad. I could enter an appointment on any device and know that it would show up immediately on all the other devices. And I could share calendar data easily with others, whether or not they were MobileMe users. All that changed last week with Apple’s latest calendar update.

Pointless error message from Apple when it fails to sync with itself

The first thing the update does is pointlessly duplicate all your existing calendars, so that you have double listings of all events.

To stop that nuisance, you have to choose which version of each calendar to stop displaying: the new one hosted at MobileMe, or the “old” one that is locally cached on all machines and is in the fact the same thing. With no information from Apple, I guessed that I should stop displaying the “old” sync’d calendar and instead display the new MobileMe copy.

This caused the “old” calendars to disappear from my sidebar entirely. Now when I create a new event, there is much spinning of the beach ball as the cloud and my local computer negotiate every character press.

That’s bad enough; losing all calendar data is worse.

When I rouse my home machine in the morning, it fails to sync with itself due to some asinine unknown problem in Apple’s cloud, sends me the pointless error message shown here, and gives me a calendar like the one at the top, which is completely empty except for locally cached birthdays. Restoring the calendar requires me to stop work, quit any open apps, and restart my machine several times.

Additionally, “old” calendars long shared with others don’t update. You have to tell the user to stop linking to the “old” calendar and send info about the new one. And the new one won’t work if the user isn’t on MobileMe.

I’d happily go back to the “old” calendars that were always locally cached, never got hiccups when I typed data into them, and never disappeared like this, but Apple has helpfully removed them from my sidebar, so I can’t. I’m stuck with poor performance and disappearing calendars.

Things work better some places than others—for instance, on my iPhone, where I use Calvetica, I haven’t suffered the same frustrations I’ve experienced on my home iMac—and of course your mileage may vary. No doubt Apple tested the update on at least a few user setups, and I’m sure there are people for whom the .0 update is working, but I’m not one of them, and you might not be either. Eventually Apple will fix these bugs. I suggest waiting until they do. There is no benefit to the new calendar for existing MobileMe users, and there are plenty of drawbacks for now. I love Apple but their usability testing sucks.

19 thoughts on “Hold off upgrading MobileMe iCal

  1. I know it doesn’t help much – but in future you might want to occasionally use the:

    File > export > iCal archive

    command in iCal so save backups of your data.

    If you have Time Machine running – you could attempt to bring back the iCal data.

    It’s a shame that Apple’s attention to detail can suck… and some parts of MobileMe do feel that they were rushed and only half finished.

  2. Agreed. I upgraded when it was first in Beta and it sent out cancellation emails to all my subscribed events. People emailed me saying, “Why did you cancel?” I had no explanation, no outgoing emails. Called Apple and they suggested I downgrade. So I did. Waited 6 months and eventually had to upgrade again. Thought the issues would be fixed. Nope. Same issue– sent emails out cancelling subscribed events. I spoke to Apple again and they explained how the new iCal is supposed to work but they still have no explanation for why it deletes and sends out these emails. I have been an iCal user for several years. After spending several hours trying to fix the issue and explaining to co-workers why I had “cancelled” events, I finally ended up switching to Google calendar because of these issues. Now I’m back on Busy Cal. But, I refuse to even open iCal for fear of these issues.

    I had backed up all my calendars so I was able to restore most of the events. The issue for me when the calendars are deleted was that it sent out these cancellations automatically. And I pay for this??!!

  3. > I love Apple but their usability testing sucks.

    Actually, this isn’t usability testing at all. (My telling Jeffrey Zeldman this is indeed teaching my grandmother to suck eggs, but there you are.)

    The problem here is functional testing, or (to be precise) integration testing, in the presence of error. And that can be exquisitely hard. Suppose, for example, that your data has a problem that appears only in some user’s files. Risk factors include

    – the user has lots of calendars
    – some of those calendars have been used many times
    – the user takes advantage of lots of features, including obsolete and seldom-used features
    – some calendars date back to early iCal releases — or before!
    – some calendars are shared with Google, with Calvetica, with BusyCal, with…
    – calendars are sync’d with more than three machines in multiple locations
    – the user once used ________, an early-release or beta product that is now forgotten by everyone.

    You’ve got ALL these risk factors in spades, and I think all of these are plausible risk factors for things that could give a sync program fits. So do lots of other people. I’ve got them all, too. But if you went down to the Apple store this morning and grabbed 20 people for usability testing, you might not get any of them.

    Sync is exceptionally tricky to get right, and if it’s not exactly right it often spreads bad data throughout your network. Once that starts happening, it’s very easy for reasonable users to attempt corrective steps that wind up making things worse. (What complicates this in Apple’s case — and what is, I think, your real beef with the designer here — is that in the interest of “usability” the sync services tend to be extremely terse and reticent about error reporting. They don’t give you silly warning messages the way Microsoft products tend to do, but when things go bad, they sometimes go bad without much fuss or warning.)

  4. You may have more luck syncing iCal with Google Calendar. It works flawlessly across devices. If you’re an iPhone user you may not get cloud syncing, I’m not sure on the limitations of the mobile calendar app outside of the old USB sync.

  5. Mark Bernstein, this is interesting and useful info and gives me an insight into the challenges of the design problem. Thank you, I greatly appreciate that.

    At the risk of repetition, though, keep in mind that sync worked brilliantly and perfectly across all my machines and devices until this upgrade, and the upgrade added no new features, as far as I can tell (it just broke stuff that used to work).

    My theory, which dovetails nicely with the information presented in your comment, is that this upgrade may benefit entry-level users with simple set-ups, making it easier or more obvious for them to do things that I already do (or did until the upgrade created trouble for me).

  6. Ok so round two of troubleshooting
    1) this looks like some ical problem. try moving ical’s preferences somewhere else then reopening
    2) reset sync history, really.
    3) your keychain might have problems if the mobileme password vanished. try repairing it.

  7. Did you try resetting your sync services?

    Of course. Didn’t fix problem. Calendar behavior still flaky as described here and on Flickr page. App freezes when trying to create a simple event, etc.

    reset sync history, really.

    I think you mean “reset sync services.” I did that. (Is sync history different?)

    What does the sync diagnostic assistant say?

    What is that?

    try moving ical’s preferences somewhere else then reopening

    Scary, but I’ll try it next.

  8. You appear to still be able to downgrade. If you do try this though, back up everything as many times as humanly possible!

    Then try going here when logged in to the MobileMe website – https://www.me.com/calendar/downgrade/

    Cross your fingers and press downgrade. That should revert you (but it loses any calendar changes you’ve made since the upgrade).

    Then I removed the MobileMe CalDav account from iCal and then synced with MobileMe again which brought the old calendars back.

    I’ve no idea whether the invites/sharing preferences will revert as well, but the process of downgrading to the old local-style calendars worked for me.

    Hope that helps,

  9. Agos:

    I owe you.

    After removing *all* iCal-related preferences from the Preferences folder inside the Library folder inside my user folder, I was able to restart iCal and have it behave like iCal instead of like a frying turd.

    Files I removed:


    Nothing appears to have been harmed by removing those files from the Preferences folder. I can’t guess which of them became corrupted or why, but the app opened fine without them. I’ve since been able to create and delete new events, to sync events, to quit iCal and re-open it and not lose events or the layout, and not freeze, etc.

    Thank you.

    I stand by my recommendation not to upgrade at this time. Whatever happened, happened because I upgraded. I didn’t gain any functionality from the upgrade, and my friends and colleagues who subscribe to certain calendars of mine can no longer do so unless they upgrade their OS, etc., making the whole thing a lot of bother for no gain.

    BUT now that my calendar *works* again, I am beholden to you, Agos.

    Are you attending SXSW or An Event Apart?

  10. My iPhone hasn’t synced with MobileMe since October of last year. My geek son worked on iCal and MobileMe syncing recently and it still doesn’t work. The only way I can get events on my phone is to sync from the computer with iTunes. However, it does seem to sync from phone to MobileMe. Don’t know why it will sync one way and not the other.

  11. The only file you should trash when that happens is: com.apple.iCal.plist
    Once that’s trashed, everything should go back to normal.

    On a side note. I sent you an email inviting you to a graphic design lecture series that will be held in Puerto Rico in September 2011. Just let me know if you’re interested.

    Regards, E. Amador

  12. Hi again!
    Glad you managed to make iCal work again. Sorry if my suggestion were a bit too concise to the point of looking harsh: I understand the frustration of finding a data loss, so I tried a quick troubleshooting, but couldn’t articulate better because of time constraints.

    While the new MobileMe calendar has been very reliable on my setup, your suggestion of holding off is still a sound one, especially for those who depend heavily on it, considering mobileme’s less than stellar reliability record; the necessity to rethink one’s calendaring sharing workflow, if applicable, would be another big drawback. I’ll also second the suggestion to take into consideration busyCal, especially if you need Google calendar syncing or syncing over LAN.

    Again, I’m glad your iCal is now behaving!

    To answer your final question: sadly, I won’t be able to attend neither SXSW nor An Event Apart this year, since I live on the other side of the Atlantic, and my student status means it would be a bit impractical.



  13. @Paul Stone.
    Thanks man, you saved my day! After working for half a day to get it right, i found your post and downgraded and all is fine again thanks to having had backups! Now all is fine on ical again!
    @EVERYONE : If you did participate in the beta, do not upgrade ICAL. I had upgraded to Beta on my mashine and i am fine. But my girlfriend did upgrade last week to non beta and got in a mess! But thanks to backup and downgrate, she is up and running again!

  14. I to lost functionality and can only sync between iphone and mobile me.
    I had to restore ical as it was erased but nothing created in iCal syncs with the iphone or Mobile me.

    I beleive they did this to get people to upgrade, soon we’ll need to jailbreak out iMac’s.

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