Synchronize Outlook 2016 Calendar with iCloud Calendar

How do you set up Outlook 2016 calendar with iCloud calendar?
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Edwin HofferTechnical ExpertCommented:

Follow the steps:

1. Close Outlook and Open iCloud
2. Login with Apple ID
3. Select “Mail, Contacts, Calendars, and Tasks”
4. Click on Apply and Select All calendars, contacts, and tasks in next option

Blakie32Author Commented:
The calendars will not sync correctly but that could be something my Firm is blocking.  Security does not allow certain things.  So I am closing the ticket.  Thanks for your help.
Is it not syncing at all?  How are you connecting your Apple Mail?  What's running on the Back end?  On Premise Exchange?  Office 365 Exchange?

Those determine how you connect.  You can connect Apple Mail to exchange, but you may have to manually configure Exchange server.  If Outlook can syn, then so can Apple Mail.  You may be connecting incorrectly.
Blakie32Author Commented:
I am not trying to connect the Apple Mail.  Here is how we are set up and what the user wants to do:

1.  We have Outlook 2016 (64-bit) here at work on Exchange 2013.
2.  The user wants whatever appointments he adds to his Outlook 2016 calendar to also appear in is iCloud calendar where they can log into "", go to Calendar and see those events.
3.  He will not be adding anything to the calendar in iCloud - it will always be from his Outlook 2016 at work.

So when I have created calendar items in Outlook 2016 (and I have the "iCloud Outlook Add-in" enabled), it is not showing in the iCloud.  From research, it stated I just need to install the Outlook plug-in on the Windows' computer I will be using which I did and have the Add-in but the calendar items do not show.
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