Unable to setup iCloud to sync with Outlook 2016

In iCloud Settings, if I select the option to sync Contacts, Calendars and Tasks with Outlook then Apply, it just sits there saying "Setting Up..." with a spinning wheel.


I've tried uninstalling and reinstalling iCloud. I've tried doing this with and without Outlook running.


If I close iCloud Settings and reopen it, the option to sync is no longer selected.


After reinstalling iCloud, the iCloud Outlook Add-in was inactive. I changed it to be active at startup. However, I still don't see the iCloud data file or the corresponding entries that should be there under Contacts, Calendar or Tasks.


Any suggestions on how to resolve this problem?

Posted on Jul 20, 2016 9:55 AM

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6 replies

Aug 14, 2016 2:42 PM in response to KenRider

I have the same problem. I'm running Office 365 Home version 16.7070.2033 and iCloud version 5.2.1 on Windows 7. iCloud Outlook Add-In is enabled within Outlook. I get the perpetual spinning wheel in the iCloud window when check the box next to "Contacts, Calendar, and Tasks With Outlook" and then click "Apply". I have found a few others with the same issue with no successful solutions except to use the MSI installation instead of the Click and Run installation. MSI installation is not available for Office 365 Home.


Has anyone solved this?

Sep 7, 2016 5:09 PM in response to KenRider

I don't know if there was a software update or not, but I finally got it to work. Every previous time I installed iCloud (and it was several), I chose the option not to send Apple usage information. This last time I selected to send usage information to Apple. Then the installation setup my contacts OK. I guess Apple doesn't like it when you don't give permission for them to monitor you.

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Unable to setup iCloud to sync with Outlook 2016

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