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Dear @Hahne Masley
SMTP 550 means a mail server rejected the message. The number alone doesn’t tell us why. I’d start by opening the delivery failure notice and looking under Diagnostic information for administrators for the full line after Remote server returned. For example, 550 5.1.1 typically points to a recipient address problem, while 550 5.7.1 can indicate a permissions or mail policy restriction.
Please refer to this document: Fix NDR error "550 5.7.1" in Exchange Online
- If it happens with one recipient: Verify their address through another channel, then type it manually in a new message instead of selecting the saved Outlook suggestion.
- If it happens with several recipients or domains: Ask your Exchange administrator to run Mail flow > Message trace in the Exchange admin center for one failed message. Give them the sender, recipient, and approximate send time so they can check where the message was rejected. Please refer to this document: Trace an email message in Exchange Online
Could you share the full 550 error line with email addresses hidden, and let me know whether it affects one recipient, one domain, or several domains? That will help me suggest the right fix.