MessageID incorrect when send emails with Authenticated SMTP

Jhon Fredy 1 Reputation point
2021-04-18T23:05:36.713+00:00

Hi Team,
We are having problems when we send emails with Authenticated SMTP (587)
The following is the situation:
When we send emails from OWA in the destination we see the message id as <618fb1b9818e43388950e9ada6d12c44@externaldomain.com>
When we send emails though Authenticated SMTP in the destination we see the message id as <618fb1b9818e43388950e9ada6d12c44@ECHANGE.internaldomain.local>

This behavior is causing that our emails send via Authenticated SMTP arriving in the destination as Junk Emails.

What configuration is missing with Authenticated SMTP?

Thanks for your help

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  1. Kael Yao-MSFT 21,911 Reputation points Microsoft Employee
    2021-04-19T09:13:27.06+00:00

    Hi @Jhon Fredy

    From your description, the internal AD domain (internaldomain.local) doesn't match the external mail domain (externaldomain.com) in your environment.

    I suppose that emails sending via OWA worked fine and the only emails sent via Authenticated SMTP were marked as spam.
    Do other recipient domains also reject the emails or it is just the specific recipient?

    According to this link: Message tracking
    89073-07.png

    If Message-ID isn't set in the SMTP application, Exchange server would set it in the form of <guid@serverFQDN>.


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