OME Custom Template is not applied when a message sent from Exchange Server (Hybrid)

Mr. Peterson 266 Reputation points
2021-10-21T11:19:45.15+00:00

I set up a transport rule to apply Encryption and "customize rights protect message with template" when a certain keyword is used in the subject.
When I sent an email from Outlook (or OWA), the mail gets encrypted and a proper template is applied. However, when I send an email using our local SMTP (we have a hybrid with connector from Exchange Server to Exchange Online), only Encryption is applied, but template remains default.
In terms of Mail Flow the mail passes the same transport rules and goes the same route. I tried to use separate transport rules (one for Encryption and another one for Custom Template), everything works in EO, but when I send the same from Exchange Server, template is not applied no matter what.
Have anyone encountered that problem and managed to fix that?

Microsoft Exchange Online Management
Microsoft Exchange Online Management
Microsoft Exchange Online: A Microsoft email and calendaring hosted service.Management: The act or process of organizing, handling, directing or controlling something.
4,212 questions
Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
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  1. KyleXu-MSFT 26,211 Reputation points
    2021-10-22T05:37:08.947+00:00

    @Mr. Peterson

    In a hybrid environment, Exchange on-premises emails will be sent from Exchange on-premises to Internet directly. Outbound messages to the Internet

    Then, about sending email from command, I would suggest you relay email from Exchange online with 587 port. Because, you even could use a nonexistent email address to relay email successfully when using 25 port to relay email. It is different from sending email from mail client.

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