Hi jgies,
Thanks for those details. Were you able to try these specific steps in the resource?
"Microsoft Windows
After each step, check your contacts, calendars, or reminders.
Reminders are called Tasks in iCloud for Windows.
Click Refresh
in Outlook.
- Open iCloud for Windows.
- Deselect Mail, Contacts, Calendars and Tasks, then click Apply.
- Wait a few seconds, select Mail, Contacts, Calendars & Tasks, then click Apply.
- Open Outlook.
In Outlook 2010 and later:
- Click the File menu.
- Click Options in the left panel.
- Click Add-Ins in the left panel of the Outlook Options window.
- Look at the list of add-ins in the Active Application Add-Ins section.
- Select the iCloud Outlook Add-in.
Learn how to manage Add-ins with Microsoft Outlook.
In Outlook 2010 and later:
- Click the File menu.
- Select Info > Account Settings > Data Files.
- If iCloud is the default account in the Comments column, select a different account, and click Set as Default.
After you restart your computer, see if you fixed the issue."
If so, contact Apple Support for further assistance.
Takecare.