Sync Outlook, iOS Calendars

My wife and I had what seemed on the surface to be a simple goal: establish a shared, online Family Calendar. My calendar is kept on my Apple devices, either my iPad or iPod touch. My wife, on the other hand, keeps her calendar in Microsoft Outlook (which contains the bulk of family events).  My Family Calendar simple request now required bridging the Apple, Microsoft worlds and the mobile, desktop worlds. Could this be done? Ultimately, yes, but not without some bumps in the road.

Sharing your iOS Calendar 

I had already done the first step: sharing my iOS calendar with my wife.  To do this, Edit the calendar you want to share, and add the person(s) under "Shared With".

Outlook sharing turned on

iCloud  Outlook calendar sharing checked

From this point it seemed clear what to do: install iCloud on my wife's laptop, configure it to share her Outlook calendar, and we should be good to go!

In short order I accomplished both of the above, and for good measure told Outlook to share, turned it on, and...nothing.  Nada.  Zip.







She dutifully continued to make Outlook calendar entries, which my Apple devices dutifully ignored. So much for easy cross-platform syncing.

After additional testing, the problem (surprise, surprise) seemed to lie with Outlook. Even though iCloud was set up for syncing, it seems the native Outlook calendar is not syncable.  The solution: ditch the native Outlook calendar and make all calendar entries in the shared (but different) calendar in Outlook.

Outlook showing only the shared calendars

This seems to work well. Outlook can be set up to show all calendars, shared and unshared. If you make entries in the shared Outlook calendar, iCloud will pick these up and sync it to your shared Apple devices. When my wife would create/change calendar of events in her Outlook on the shared calendar, these would be synced over to my mobile iPad and iPod touch.




However, a big problem remained: how to get the several dozen existing events from her native and unshared Outlook calendar over to the shared Outlook calendar. This would seem to be easy: do a  Select All/Copy in the original calendar and then a Paste into the shared calendar. Alas, Outlook won't let you do a Select All/Copy from the calendar view.  In Outlook 2010 you can change the calendar from a calendar view to a List view and then you can do your Select All/Copy/Paste from one to another.

Outlook 2007 View by Category

But my wife still uses Outlook 2007, which doesn't have a calendar list view feature. After a few more deadends, I found the answer: if I switched her native calendar to a "View by Category" view, I could copy all the entries from the native calendar and paste them into the new, shared calendar.




This worked!  All her original calendar entries then synced between our two calendars and -  finally - we had a Family Calendar shared between Outlook and iOS!

So, in summary, to sync your Outlook Calendar with your iOS devices:

1. Share your iOS Calendar
2. Install iCloud on your PC
3. In Outlook, copy your native Calendar to an iCloud shared Calendar
4. Make future changes only to the Outlook shared  calendar

Outlook Calendar Event now shows on my iOS Devices