question

JhonFredy-3502 avatar image
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JhonFredy-3502 asked JhonFredy-3502 commented

MessageID incorrect when send emails with Authenticated SMTP

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

windows-serveroffice-exchange-server-connectivity
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1 Answer

KaelYao-MSFT avatar image
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KaelYao-MSFT answered JhonFredy-3502 commented

Hi @JhonFredy-3502

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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Hi,
Thanks for you replay.

We do some test and sending emails via Authenticated SMTP to GMAIL and HOTMAIL and these messages arrive to inbox without problems.
We see this issues when we send emails to another exchange on-premise (Exchange Server 2013 with latest CU)

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Hi,

Thanks for the update!

Does the recipient side have some third-party anti-spam gateway?

If not and the messages is marked as spam by the Exchange server,
as a workaround, I suppose that you may need to ask them to setup a mail flow rule to bypass the relayed messages.

The rule would be like:
89472-11.png


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11.png (20.7 KiB)

Hi @JhonFredy-3502

I am writing here to confirm with you how thing going now?
Did the issue get resolved?

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Hi,

Thanks for the suggestion, i will try this.

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