Hi Dan Simpson,
Thank you for reaching out to us. I'm glad to help you!
To better assist you and identify the root cause, I’d like to kindly ask for a few additional details:
Could you please confirm whether your Outlook account is a personal or business account?
Just to clarify, did this issue occur specifically on the Outlook app for iOS?
If possible, could you try to reproduce the issue on: Outlook Web, Outlook Desktop, both Classic and the New Outlook experience?
Could you let us know what type of account you’re using? (POP, IMAP, or Exchange)
When you have a moment, please check if there are any Inbox Rules that might be affecting your ability to send emails.
Are all outgoing emails being returned as undelivered, or is this happening only with certain emails?
If specific, are the recipients internal (within your organization) or external?
Are there any common patterns, such as file attachments, message formatting, or subject lines, between the affected emails?
Once we have this information, we’ll be in a much better position to investigate further and work toward a resolution. Thank you again for your patience and cooperation, I truly appreciate it. Looking forward to your response!
Sincerely,
Jeanie-H - MSFT | Microsoft Community Support Specialist.