Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi, CyberT
Good day!
Thank you for posting to Microsoft Community. We are happy to help you.
According to your description and detailed information, the issue of your concern that your Outlook cannot connect to server.
Thanks for all your attempts from the above, at this moment, please be kindly to give an attempt for following steps:
Please hold Ctrl + Right click on your Outlook icon > Click Test email Auto Configuration >Untick 2 selection as below > Test it.
Also, please hold Ctrl + Right click on your Outlook icon > Click Connection Status ( click reconnect if there's a selection on your-side and see if it can make any differences.)
In addition, please be kindly to download Support and Recovery Assistant to repair Outlook:
Download Microsoft Support and Recovery Assistant from Official Microsoft Download Center and share the analysis results with us for further assistance. (We would be highly appreciated it if you can capture the detailed error or screenshots to us for further assistance.)
What's more, could you please allow us to confirm whether if the issue relates to the Basic authentication with an IMAP account?
If so, please be kindly to refer - Configuration for IMAP, POP and SMTP with OAuth in Exchange Online - Microsoft Community
Redirecting.
We're glad to help you and looking forward to your new updates.
Sincerely,
Alex | Microsoft Community Moderator.