Using the New Outlook for Mac features in business environments
Dear A Shep
Thank you for posting in the Microsoft Community.
I understand your situation and needs. May I ask you a few questions? If I could learn more about your email and the situation you are experiencing. I could provide more accurate help. Thank you for your understanding and support.
May I ask if your email is a Microsoft domain email like outlook, hotmail, live, msn? Or is it a third party email for other domains?
You say a random contact sent you an email that bounced and was undeliverable. Can you ask your contacts to provide you with an explanation for the bounced emails? Because the official Microsoft postmaster bounce notification will include an error code and description of the error. I would need to be directed to the specific error description to understand exactly why the delivery failed.
You can do this in New Outlook by clicking Settings -> Mail -> Junk Email in the upper right corner. See if these contacts are in Blocked Senders and Domains. Then add them to Safe Senders and Domains to ask them to send again.
Click Settings->Mail->Rules. See if a rule was created stating that it causes emails from specific contacts to be blocked.
I look forward to your reply. Thank you for your support.
Best Regards,
Simon.W - MSFT | Microsoft Community Support Specialist