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David Kamp's avatar
David Kamp
Brass Contributor
Apr 20, 2018
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OnPrem SMTP sending to Office 365 Encrypted

I have Internal servers relaying on a "on premise SMTP server" this smtp server has an Office 365 Exchange Connector configured a:

From: Your organization's email server

To: Office 365

Identity: from our Public IP that the smtp server sends from.

All works Great.

Now I have been asked if we can have the message encrypted or use TLS between the smtp server and Office 365.

Can that be done? without encrypting from every account that is being relayed.

if so how?

Thank you

David

  • It's generally assumed that when you configure TLS, you would use a certificate associated with specific domain, so that the service can verify the sender. If you use the IP option, you should still be able to toggle the TLS requirement via PowerShell:

     

    Get-InboundConnector Hybrid-In | Set-InboundConnector -RequireTls $true

5 Replies

  • Hi David,
    By default when you run Hybrid Configuration Wizard it will configure the TLS base on you certificate by default.
    • David Kamp's avatar
      David Kamp
      Brass Contributor
      When I edit my Connector, On the question of: How should Office 365 identify from your Mail server? I am selecting my IP Address and then do not have an Option for TLS and the summary does not indicate TLS.
      • VasilMichev's avatar
        VasilMichev
        MVP

        It's generally assumed that when you configure TLS, you would use a certificate associated with specific domain, so that the service can verify the sender. If you use the IP option, you should still be able to toggle the TLS requirement via PowerShell:

         

        Get-InboundConnector Hybrid-In | Set-InboundConnector -RequireTls $true

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