Microsoft Outlook 2011, iCal and iCloud

Almost as expected, there would be some Outlook 2011 issues with the introduction of iCloud this week. But this time, I blame Apple as much as I normally blame Microsoft.

For me, the issues was that my Outlook calendar went missing (as always). As many Outlook users, I use Sync Services to sync between Outlook and iCal, and therefore with my iPhone. But after I installed the latest Lion update, that laid the pavement for iCloud, and signed up for it, the Outlook calendar went blank. All of my calendar entries remained in iCal, but they did no longer talk.

Maybe a simple fix for this would be to turn of iCloud for my calendar, and just continue to sync that old school? Well, it turns out that when you turn of iCloud for the calendar, it removes iCloud content: And iCloud content means your entire calendar, even if the entries originated from iCal to begin with. Nice feature, Apple! If you turn it off on the iPhone, you can choose if you want to keep the calendar entries.

Deactivate iCloud warning
What do mean "user friendliness"? We've stopped doing that.

If you try to export your iCal calendar as an iCal archive, turn off iCloud, and import, the iCloud will be turned back on automatically.

So my solution to keep a happy sync between Outlook and iCal, was to export each calendar (for some reason I have many) from iCal as  .ics-files while on iCloud. Then turn of iCloud, import them in iCal, and we were back were we was before the update. If you want to merge some of your calendars you could do so, or keep them separated.

Export ics from iCal
Export ics from iCal

(Update 14/10: As Ian points out in his comment below: If you have a Time Machine backup of your system from before you turned on iCloud, you can use that for a roll back.)

Another solution would of course be to abandon Outlook, at least until something pulls out a finger from somewhere, and fixes this.

So now I can once again sync Outlook with my iPhone. Surprisingly, the address book sync works like a charm.

Maybe I’ll just go back to pen and paper.


  • Michael
    Posted 14/10/2011 at 02:35 | Permalink

    I found the exact same thing. Boom, every Outlook calendar entry eliminated. Poof, gone. So I exported every iCal (Cloud) calendar onto my desktop, imported into Outlook, disabled iCloud for Calendar, and went back to Sync Services and my USB cable. Works like a charm. Until iCloud includes Outlook 2011 for the Mac, my head will be on the ground (and not in the cloud).

  • Dcu
    Posted 14/10/2011 at 07:05 | Permalink

    Wasted hours figuring this out. Had the same issue with Outlook Calendar disappearing the minute iCloud starts to sync. Did the same as above to restore events to my Outlook.

  • Paolo
    Posted 14/10/2011 at 07:17 | Permalink

    Thanks really pretty helpful, I hope that soon someone (Microsoft /Apple) will fix this. Regards

  • Ian
    Posted 14/10/2011 at 09:29 | Permalink

    Sort of the same here. Luckily I made sure I had a TimeMachine backup and so, turned off iCloud and restored the whole /Users//Library/Calendars.
    Interestingly mine is NOT syncing Address Book, so I have had to disable that too.
    Remember, when you enable iCloud, your data is (in theory) no longer stored on your computer, but ‘in the cloud’, so… I am waiting for Mircosoft to change the sync setup and add a new option in the Sync Services control panel to say ‘iCloud’, not just ‘On my computer’.
    Holding breath!

  • Ingo (from Germany)
    Posted 14/10/2011 at 11:05 | Permalink

    Got the same problem, but (providentially) I made a back-up of my iCal and Adressbook before switching on the iCloud. At first it seemed, that it will work with Outlook. Because Outlook still connects with iCal and Adressbook, but just with a local Adressbook/Calendar. The data in the iCloud are not affected.
    So I also turned off the iCloud, re-installed the Back-Up, and switched back to the “old-school” sync via iTunes. Well, now wireless.
    I’ll hope Microsoft will fix its Outlook API for the SyncServices that Outlook will work with iCloud as well.

    Kind of interesting: iCloud works fine with Outlook for Windows – every sync between iPhone, iPad and Outlookis just perfect.

  • Rik
    Posted 14/10/2011 at 12:18 | Permalink

    Hi guys,

    How do you get all your appointments back in the Outlook 2011 Calendar?
    I used Time Machine to restore a backup of the iCal calendars, back to the old “On my computer” version which should be able to sync with Outlook.

    But it doesn’t. Outlook Calendar stays empty. Turned off/on the sync services in Outlook but without results???

  • Brock
    Posted 14/10/2011 at 21:59 | Permalink

    Tried the above approach with Entourage 2008, but no luck. Was able to archive, turn off iCloud on iPhone and mac, and get the iCal working with back-up. However, no sync with Entourage.

  • eric
    Posted 15/10/2011 at 09:58 | Permalink

    Hmmm…….my problem is more serious and I have already wasted an entire day on this. My outlook 2011 does not sync with anything. iCloud of course works fine with Ical and Address Book but my ical and address book are NOT syncing with Outlook. I have tried 3 tests. First update record in Outlook. Does not appear in either iCloud or Address Book. Second add record in Address book……of course appears in ICloud but does not appear in Outlook. Add record on iCloud…..once again appears in Address Book but NOT in Outlook. I have been on numerous sites to resolve this and have found no solution that works. I have even shut down iCloud and started from scratch. Erased all contacts from Address book and imported them anew from Outlook which at least got rid of all the duplicates. Clearly Microsoft and Apple are still NOT talking. I love my Outlook and won’t give it up. The only thing that works seamlessly is my e-mails. THANK GOD FOR THAT!

  • Ethan
    Posted 16/10/2011 at 20:03 | Permalink

    When I updated Lion and turned on iCloud my Outlook 2011 calendar disappeared also, but then several hours came back. What I now have are single entries for contacts and calendar events in Outlook, and dual entries in both iCal and address book. One is “on my mac” one is “iCloud”. Calendar entries and contacts synch both ways between Outlook and the “on my mac” entries in iCal and address book, respectively but not with iCloud. Likewise, iCloud entries synch with iCloud on line but not with Outlook. I plan to get an iPhone soon. Probably the best thing is just synch it through iTunes and not try to mess with iCloud. I’m afraid if I disable it that my calendar will disappear again from Outlook, leaving me stranded.

  • Kaspar
    Posted 17/10/2011 at 14:57 | Permalink


    I had that problem as well for a while (Outlook not syncing with iCal and Address Book. I got it to work again by rebuilding my Outlook identity (to do that, hold the Option key while starting Outlook, then choose “rebuild”). Not sure why this worked, but it did. Also not sure whether you might have to turn off iCloud first for this to work.

  • Rob DeSimone
    Posted 18/10/2011 at 19:40 | Permalink

    Interested about your comment that Address Book works. It doesn’t for me. I ended up with a duplicate set of contacts in Address Book — one “on my Mac” and one “on iCloud”. I was able to get rid of the duplicate Address Book but now my Outlook is blank. Turns out the iCloud calendar doesn’t talk to Outlook.

  • kapil
    Posted 18/10/2011 at 20:07 | Permalink

    the issue with the icloud calendar sync with outlook is scary. I exported the icloud calendar onto my desktop from my outlook and then imported it onto my outlook calendar. all the meeting and blocks came back and then I went into my file -> data file management and removed the iclould folder.
    my appointments are back on the schedule. also i noticed that any meeting that i had without an end date, once i synced my calendar on icloud. a meeting invite was sent out on all those meetings. that was a bad first half of the day for me

    hope you find it useful as someone said … my head will be out of the cloud for a few days as well.

    hope you find it useful

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  • Ethan
    Posted 19/10/2011 at 23:51 | Permalink

    OK – one other problem. After finally straightening out my calendar on Outlook and iCal, and turning off iCloud, I went to my iCloud account and deleted my calendar since I wasn’t using it anymore. BIG MISTAKE!!! Without asking iCloud sent an e-mail message to everybody who ever invited me to a meeting past or future telling them that I had declined their meetings. For past meetings it just cluttered their inbox, but I received queries from many people asking me why I had bailed on future meetings I’d already accepted. Took me all afternoon to do damage control. For iCloud to just assume I wanted to do this and send out hundreds of messages under my name without asking is horrible arrogance. This is the kind of terrible implementation I’d expect from Microsoft, not Apple.

    • Jan
      Posted 19/02/2012 at 06:12 | Permalink

      Same happened to me…I am back to the old way of syncing outlook 2011 with iCal and then use Wifi or USB to sync with iPhone/iPad.

  • Michael
    Posted 10/11/2011 at 11:37 | Permalink

    How I restored my Outlook 2011 calendar after iCal/iCloud deleted everything.

    1. Disable Sync Services in Outlook and quit.
    2. In iCal, open the calendars list and right click the iCloud calendar that has all your Outlook data. Export it.
    3. In iCal Preferences, disable your iCloud account.
    4. Disable iCloud Calendar Sharing in System Preferences.
    4. In iCal, do File > Import > Import and select the file you exported in Step 2. iCal will ask which calendar to import it to, so make sure you select a local calendar.
    5. Open Outlook and re-enable sync services. Your calendar data will reappear.

    • Anna
      Posted 30/01/2012 at 16:20 | Permalink

      My data didn’t show up in step 5, I had to drag all of the exported .ics files into outlook.

  • Karl
    Posted 05/01/2012 at 16:32 | Permalink

    Just converted from PC to Mac; spent 12 hours at Genius bar attempting to get Outlook to synch with iPhone, iPad on iCloud. Result? Now using macCal instead…really miss my outlook and its functionlity any update on a fix?

    • Ron
      Posted 15/01/2012 at 05:41 | Permalink

      Hope they come up with some fix soon. I use Outlook at work and have iCloud on my laptop and iPhone. Nothing is communicating. One of the reasons I switched to Apple was for iCloud and the ability (supposedly) to sync everything. Sure isn’t happening!

  • Tony
    Posted 25/01/2012 at 22:00 | Permalink

    I’m still yet to upgrade to Lion for the worry of messing up my syncing which works at the moment.

    Any news on all this? Still no solution I guess?

    I spoke to Microsoft and they said it should all be fine? well yeah, “Should”

    I have not even dared upgrade to ios5 either for the stress of getting a non-syncing situation…

  • Mike
    Posted 12/02/2012 at 22:59 | Permalink

    Too bad the synchronization is just not there….yet I’m a recent convert to Mac from PC after loving my iPad and iPhone. Trying to hang on to Outlook is becoming increasingly frustrating. It’s too bad that Pocket Informant doesn’t have a Mac app. …

    There just doesn’t appear to be anyway to automate replication/synchronization between iCloud & Outlook … Extremely frustrating!!

  • garrett
    Posted 14/03/2012 at 06:44 | Permalink

    all you have to do which isn’t the most convenient is duplicate the entry on on mac and one on iCloud..its very quick to do and the result is having sync between iCloud, ical, and outlook. its easy i saw this was mentioned above…

  • Marc
    Posted 16/03/2012 at 20:01 | Permalink

    I also had a problem with all my calendar entries disappearing. I do not sync with anything. Turns out I had accidentally unchecked the ‘Calendar’ box which controls which categories are viewed.

  • Steve
    Posted 30/03/2012 at 06:48 | Permalink

    Because I don’t directly attach my iPhone to my office PC and sync with the company’s Outlook client (due to heir security concerns), I forwarded a meeting request as an attachment to my personal gmail account to get it on my iPhone calendar, somehow by clicking the .ICS file attachment and choosing to “add to calendar on an iPhone, it made my home email account the organizer, changed the meeting time, and sent a modified meeting request to everybody in the meeting except for the original organizer.


  • Jerry
    Posted 11/05/2012 at 18:02 | Permalink

    Yep. After spending 2 days pounding my head into my desk I finally bailed on iCloud.

    iCal, Outlook 2011 for Mac, and iTunes is the way to go right now.

    Eventually it would be great to have the Calendar Sync to all my devices (when I get an iPad) but right now everything is working.

    On the bright side I did learn a lot about the SyncService function of OS X.

    • debbie
      Posted 01/02/2013 at 00:33 | Permalink

      I also have spent countless hours/days trying to sync all info perfectly (per the Apple sales associates assuring me that everything works)
      I too am using iCal, Outlook 2011 for Mac and syncing using iTunes, but my problem is not that I’m losing everything – each time I sync – I get duplicate after duplicate. If you could see my Outlook calendar now – each entry is duplicated umpteen times.
      Jerry – can you share what setting you have set up so everything ‘talks’. I’m more than happy to continue syncing via iTunes rather than using iCloud – I just want it all to work.

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