My Add-in for Outlook on Windows 10 365 iCloud will not be enabled.

For 3 months I discovered this problem. I upgraded from 2013 Office to Office 365 and to synchronize with my iPhone 6, I have to activate the Outlook add-in for iCloud, everytime I open Outlook.

I was wondering if there was a fix for this problem.

Thank you.

I have the same problem.  It worked, but it seems that the latest update to iCloud for Windows 10 broken things again.  Now the Outlook add-in iCloud get off whenever I start Outlook.  None of the solutions I found by Google (whether for iCloud or Outlook) works.  Meanwhile, contacts or calendar of events using my iPhone is useless since Outlook is as my master for both.

I noticed that Outlook is running in administrator mode allows the plugin remains enabled but I shouldn't do that.

Apple, would you PLEASE fix this and properly test your updates, so it continue to happen?

Tags: iCloud

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