Using classic Outlook for Windows in business environments
Hello HLT_64,
Welcome to Microsoft Community and appreciate your time taken for sharing detailed information. I understand that the problem is sending an email via outlook is getting a notification as "Sending to these recipients or groups has been completed but not sent by the target server". If my understanding is wrong, please correct me in the reply. I am glad to offer you help on this issue.
If you receive an error that a message is undeliverable, this could be due to the sending server trying to deliver the message, but the action didn't complete before the message expired. This error typically indicates a problem on the receiving server.
Try these fixes: Make sure the recipient address is valid. Reduce the number of recipients in the message. If you received this error when sending a message using Outlook or another email app, try using Outlook.com to send the message instead.
We need to go through a series of steps to find the real cause of the problem. If the above steps do not solve your problem, please let me know and I will continue to assist you with the problem.
Best Regards,
Mavis - MSFT | Microsoft Community Support Specialist
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