Still cannot get Outlook 2016 Calendar and Contacts to sync with iCloud. iCloud data file hasn't been put in Outlook but iCloud add in is active.

I fixed mine after about 8 hours of messing with it. Uninstalling and reinstalling everything. Finally,

I went to the file tab and clicked on the "Manage COM Add-ins' button. It said that iCloud was disabled. I enabled it again and it worked like magic. Such a simple fix after many hours of grief.

Same problem. I am using Windows 10, Office 2016, and iCloud for Windows 5.2. Everything worked fine for several months until a few months ago when calendar sync stopped working. I updated iCloud from 5.1 to 5.2 but that just killed it altogether. Tried uninstalling iCloud and reinstalling fresh. No luck. When iCloud settings pops up, I check the box for Calendar and Contacts. The check then vanishes. I check again and it sticks. But no messages about "setting up". When I close and reopen, the box is unchecked. A few days ago, I had the same problems from another another thread where it would show "setting up" spinning forever (well, 30 minutes before giving up). Not sure if this is an Apple problem or an Office problem. But it sure is a problem.

When I installed Office 2016 in October 2015, I was dismayed to find that iCloud didn't work with Office 2016. Within a couple weeks, a new version (perhaps 5.1) fixed the problem and it was working fine. But it stopped working a few weeks ago. Thus, the supposed "fix" of installing the latest version (5.2). But that just made it worse. One more data point, if I try to "Modify" iCloud, the "Repair" option brings up an error message about the installer. Only option is to uninstall and reinstall but, as others have found, that brings no joy. Also, I have checked to ensure that the iCloud "Add-In" is active under Outlook 2016 (it is).

Cheers,

Stewb99

I too have had this problem. The default Windows PC outlook calendar, contacts and task files will not sync with iCloud files. ICloud syncs fine across icloud, iPhone and iPad. After along time working on this (hours and hours) I finally worked up the food chain to a manager at Apple Support. The manager said that the latest versions of iCloud were incompatible with Office 365 and Microsoft exchange server.

Shame on Aplle for not telling us. We might be able to accept a limitation or a find a work around, but not telling the community and having hundreds if not thousands of people wasting their time is unforgivable. It's iAbuse.

Charlie

Hello Charlie,

Thanks for getting some info out of Apple, disappointing as it is. I would assume that they will quietly fix the problem and release a patch to iCloud for Windows - or perhaps a new version. I can't imagine that they'd simply abandon the functionality.

I have been trying to get this to work for a while, yet I stopped short of drastic actions like reinstalling Office 2016 or Windows (by the way, kudos to all the folks who made those efforts to help determine the skunk at the picnic).

I'm trying to make this work for my wife who runs a small business using her Windows 10 laptop, an iPad, and an iPhone. Having the calendar and contacts simply dead in the water is disruptive and disappointing. Do we really have to stay in our own walled off camps of PCs vs. Macs? Can't we all just get along? 😉

Regards,

Stewb99 (former Windows user - now completely in the Apple ecosystem)

This feature is very important to me, perhaps the #1 reason I like(d) my iPhone. How do we upvote bugs? How can we even tell that Apple is aware of this issue? It would be great if Apple would publish a bug number so that we know they are at least considering a fix. My issue is *not* a Click-to-Run problem. The syncing stopped either at my Windows 10 upgrade or an iCloud upgrade or some Office update in between. I'd be happy to provide logs or run a debug version or do anything else to solve the problem. Reinstalling iCloud did not help. I am loathe to reinstall Windows and Office just to see if the problem goes away.

I suppose there are a variety of things that could be going wrong. Different posters to this thread have different configurations. I solved my problem by creating a new data file (pst) in Outlook 2016 and making it my default. My previous default data file was one that I have been using since the year 2000. Prior to 2003, data files didn't support Unicode characters. Apple has clearly indicated that the sync only supports Unicode capable data files.

Actual order:

1) Uninstall iCloud; reboot

2) Made backups of all my data on iCloud and on PC; also copied all my PST files

3) In Outlook 2016, create new Data File and make it the default

4) Pointed my various mail accounts at the new Data File, but purposely didn't migrate Contacts or Calendars

5) Rebooted just to be safe

6) Reinstalled iCloud, which I think required a reboot

7) Syncing happened. The iCloud content goes to an iCloud data file, but that is OK. In my case, all the iCloud data was pushed to Outlook since I had no data in my Outlook default Contacts nor Calendar

8) Now I am in the process of manually copying the items I made while the syncing was broken, removing duplicate calendars, and trying to convince Outlook to not keep displaying the default calendar since the iCloud calendar is what I want to see.

I can't say for sure which of the above steps fixed the problem.

UPDATE: Without making any changes, I tried to get iCloud for Window to sync with MS Office 2016 again. This time it WORKED!

The bug seems to have been fixed. It looks like Office had an update done on 8/30/16 so perhaps that was the key? This is my wife's computer so I didn't see if an update went through - but date stamp show 8/30/16.

Vitals:

iCloud for Windows - version 5.2.2.87

Microsoft Office 2016 - version 16.0.7167.2040

So for all of you who have suffered through this months long drought - try it again (after running some updates) and you should be back in business.

Not sure if the skunk at the picnic was Apple or Microsoft - but I think we all simply want it to work. Finally - we appear to be there.

Cheers,

stewb99