Using classic Outlook for Windows in business environments
Dear wkrasl
Welcome to Microsoft Community.
I understand that you are having trouble on if Outlook Copilot requiring Outlook.com address.
Thank you for the detailed information, I was able to fully understand your question.
First, refer to the picture and link below. As a personal account, the prerequisite for using Copilot is to have a Microsoft 365 Personal or Family subscription, and Copilot Pro.
How to find and enable missing Copilot button in Microsoft 365 apps - Microsoft Support
If you have met the above conditions and set your @Outlook.com as your primary alias, refer to the 4-step in the URL, I think you can use Copilot in Outlook normally.
Regarding whether your @icloud.com email can use Copilot, currently no.
Of course, this does not mean that your @icloud.com mailbox will never have the opportunity to use Copilot. Be patient and wait for Copilot to be updated and improved. I believe that it will eventually be open to all emails.
Thank you for your time and understanding.
Sincerely,
Hardyjoe.J|Microsoft Community Support Specialist