Hi Scott,
According to my research, this seems to be a compatibility issues when iCloud tries to sync with Outlook.
I’d like to confirm with you whether your iCloud is up to date. If so, please try following steps and then check the results.
1. Make sure Outlook is closed.
2. Open iCloud; Open the Start Menu and simply type “iCloud” should return “iCloud Desktop app” as a result.
3. Press the Sign out button.
4. When prompted whether you want to keep a copy of your iCloud contacts, calendar and tasks, choose: Delete from computer.
5. Wait a few minutes for all changes to be applied.
6. Sign in to iCloud again.
7. In iCloud, select the option to sync Mail, Contacts, Calendars, and Tasks.
If you have further questions about this issue, please refer to
this article for more details.
(Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)
Hope this helps.
Regards,
Perry
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