Does Outlook for Mac Sync with iCloud Both Ways?

[CoMoMacUser]

I run Outlook 2011 on my iMac. I want my Outlook calendar synced with the Outlook 2011 calendar on my MBA and with the calendar on my iPad.

My iMac runs Snow Leopard, and my MBA runs Mountain Lion. I would upgrade the iMac to ML if iCloud will sync all three devices' calendars in both directions. Does iCloud do that?

Outlook 2011 doesn't support CalDAV. But can I get around that by having Outlook sync with iCal, which then syncs with iCloud to push the changes to my other machines? I asked an Apple sales rep, and she said yes, but they've been wrong about other things. Meanwhile, some users say yes, and others say no.

Bottom line: I need to have all three devices' calendars automatically synced every time I make a change on one of them. Does iCloud achieve that?

Thanks.

 

[BrianBaughn]

Perhaps someone else has a miracle solution with the train wreck that is Outlook 2011 and iCloud, but I'd say you're looking at big headaches trying to do it.

Outlook 2011 was written to sync with Exchange servers. No third party has come up with a way to make the calendars and contacts work with iCloud or even Google.

iCloud works with iOS devices and Mac applications running in OS 10.7.x or later.

To get full functionality out of Outlook 2011 you'll need to set up a hosted Exchange-type account somewhere, which is not going to be free.

 

[rbrian]

For about a week when it was launched, Outlook 2011 supported syncing with iCal - but Apple changed something which stopped Outlook Sync Services from synching. Now, Outlook 2011 syncs with Exchange, and only Exchange. There is no way to get it synched to your Mac or iPhone except by adding the same Exchange account to Calendar on Mac and iPhone. Effectively it won't be synched with Outlook, everything including Outlook will be synched with Exchange. It makes Outlook completely useless for those of us without Exchange accounts. There are threads on Microsoft's support forums going back years, with support staff saying watch this space, it's coming soon... over a year later, and still nothing has happened.

 

[CoMoMacUser]

I have two email accounts. One is IMAP, and the other is Exchange. (I'm self-employed, and the Exchange account is provided by a client, so I can't just shift my other email account onto that.)

Here's the weird thing: Sometimes calendar events created on my iMac show up on my MBA, and sometimes they don't. There's no pattern to it. For example, if my client sends a meeting request (via Exchange), and I accept it on the iMac, sometimes it shows up on my MBA calendar. Or sometimes I'll create an appointment on my iMac and in no way indicate that it's related to that client, and mysteriously it shows up on my MBA calendar. It's as if their Exchange server randomly chooses calendar events to sync.

 

[marceljanssen15]

EVO Collaborator for Outlook sync

What about when you use Outlook 2007 or 2013? Do you have the same issues?

The way I sync all my data (Macbook Air,iPhone,Windows pc etc) is with a simple add-in for Outlook. Offers me to option to 2-way sync all my devices together.

You can check it out, its called EVO Collaborator for Outlook.

Here is a related blogpost in it :
http://outlookandmacosxserver.blogspot.com.ar/2014/10/synchronize-iclouds-contacts-and.html