iCloud Add-in not working in Outlook 2013 and Outlook 2016 After Windows Upgrade & iCloud Upgrade

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DK-CDN

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Outlook version
Outlook 2016 32 bit
Email Account
IMAP
I’m in a situation where Apple says contact Microsoft and Microsoft says contact Apple.

This is about how the iCloud add-in for Outlook does not work either after an iCloud update or a Windows 10 update.

There are a number of posts on line about how to resolve this issue including:

I tried all of the above as both of my computers – one a Windows 10 desktop machine with Outlook 2013 and the second a Windows 10 laptop with Outlook 2016 both crashed when Outlook opened recently (February 22, 2020). The steps I took are outlined below.

Any suggestions are appreciated.

One suggestion I received was to uninstall the iCloud add-in, restart the PC, run disk cleanup to delete temporary files, then run an in-place Office repair and re-install the iCloud add-in. Microsoft technicians that I contacted online did NOT recommend this.

THE HISTORY:

After the recent iCloud update and a recent Windows 10 update, I was initially unable to open Outlook on either machine.

I had to start Outlook in Safe Mode (several times) and disable the iCloud add-in. Only then would my e-mail work. All attempts at trying to repair this issue have not worked (i.e. deselecting the option in iCloud for "Mail, Contacts, Calendars and Tasks - With Outlook".) or re-enabling the iCloud add-in.

Some steps I've taken are listed below.
  1. Start-up Outlook in Safe Mode, disable iCloud add-in.
  2. Shut down the iCloud app on my Windows PC.
  3. Start-up Outlook as an Administrator, remove the iCloud add-in.
  4. Exit Outlook as an Administrator.
  5. Restart Outlook as an Administrator and 'add back' the iCloud add-in.
  6. Restart machine.
  7. Log-in to iCloud app on PC and request that it sync with Outlook.
  8. Restart Outlook.
  9. Outlook opens for about 15 seconds (and you can see the iCloud items on the ribbon) and then crashes again.
When this didn’t work, I tried a different tactic:
  1. Uninstalled the iCloud add-in completely.
  2. Did a fresh installation and still things wouldn’t work – Outlook would open with the iCloud items on the ribbon and then would crash after about 15 seconds.
Microsoft Support thinks that there might have been an update to the iCloud add-in, making it not as compatible as it used to be on Outlook. It would be best to get in contact with Apple Support to see if you can get an earlier version of the add-in to see if that works on the computer (I’ve not tried this yet). Or is the issue the Windows 10 update?

Microsoft Support indicated that I have tried all of the troubleshooting steps that they were going to suggest.

Where I'm at now is:
1) My laptop with Windows 10 and Outlook 2016 shows the iCloud add-in as running, but there is nothing displayed on the ribbon (i.e. no iCloud items) and no iCloud functionality; and
2) My desktop with Windows 10 and Outlook 2013 crashes everytime I enable the iCloud add-in; I have to go into safe mode to turn it off and run Outlook without the iCloud add-in.

Thanks in advance for any assistance or suggestions!
 
I've fought this issue a few times, and it is difficult and unpredictable, not always the same solution.

I had one time where I fixed it by creating a new profile in Outlook AND using the version of iCloud that is available from the Microsoft store. (make sure the new profile you create is the default profile when you do the install). And doing the install of iCloud as an admin is probably a good idea.
 
I also found this issue much many time on my iMac laptop, in fact, I have a brand new laptop, I bought it from St. Patricks Day deals at ReeCoupons, and still facing this issue, in fact, I fed up from this issue, anyone here can help me out?
 
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