Dear SteveS611966,
Good day! Thank you for posting to Microsoft Community. We are happy to help you.
Based on your description, I understand that you have a query "Need Diane Poremsky M365 MVP ] - The Outlook/iCloud Guru's help". At this very moment, [Diane Poremsky [ M365 MVP ] may be busy, However, I believe she will reply to as long as she got this post.
In the meantime, please help providing the following information for further investigation:
- What version of Outlook are you using? Go to File > Office account > About Outlook. See What version of Outlook do I have? (microsoft.com)
- Have you checked to make sure that your PC meets the iCloud system requirements and is connected to the internet?
- Have you checked to make sure that the date and time settings on your PC are correct?
Moreover, To set up iCloud Mail in Outlook or if you don't use iCloud for Windows, set up two-factor authentication for your Apple ID and sign in to Outlook with your Apple ID username and an app-specific password. Please refer to If you can’t add iCloud Mail, Contacts, or Calendars to Outlook.
We look forward to hearing from you; please understand that our initial reply may not always immediately resolve the issue. However, with your help and more detailed information, we can work together to find a solution. Thank you for your cooperation.
Sincerely,
De Paul | Microsoft Community Moderator