Hello Johnny,
Thanks for coming back to us. To be honest, your situation is a little complex, so I did some extra researches and tests. And now I would like to share you my thoughts:
You ran Message trace before, but it shows no record there. This is because that your email is rejected by Outlook client, it hasn’t reached Exchange server yet. Non-attached emails work sometimes but attached emails don’t work at all, so the email
size might be a possible cause.
To help us investigate it further, would you mind sharing your Outlook troubleshooting log with us? Just go to
File > Options > Advanced, under
Other tab, select Enable logging (troubleshooting) check box.

After reproducing your problem, type Run in your Windows search box, then type
%temp%\Outlook Logging, press enter. This cmdlet can help you locate the Outlook logging file.
Found the OPMLog.txt and .etl files( you can send us all the logging files if it is convenience) and send it to us via PM.

Note: If you turn on Outlook log before, please clear all the file under
%temp%\Outlook Logging first and then reproduce your problem. After the log is done, please turn off the troubleshooting logging option.
Thanks you very much for your patience and time.
Best Regards,
Sylvie