Using End to end Encryption on Exchange Hybrid mode.

Waleed Waleed 0 Reputation points
2024-04-23T06:31:41.94+00:00

Hello all,

I just create a rule on exchange online to encrypt any sending email (working fine as testing), we have hybrid configuration on our environment, the weird thing when I send email from O365 email to any on premise email it shown as external

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can anyone help me with this?

Thank you.

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. Noah Ma-MSFT 610 Reputation points Microsoft Vendor
    2024-04-23T09:20:57.6433333+00:00

    Hi @Waleed Waleed,

    To help you better, I want to confirm that if all that emails from O365 send to on-premises shown as external. If no, this issue may be related to this rule. If yes, you can do the following to check:

    1. You can use EAC navigate to Mail flow > Accepted domains, check hybrid routing domain (tenant.mail.onmicrosoft.com), this domain should be configured as “Internal Relay” as opposed to “Authoritative”. 
    2. Use the following command to check the value of the send connector you use to send to on-premises from O365: Get-SendConnector "XXXX" | Format-List. Make sure the CloudServicesMailEnabled set to true.
    3. If needed, you can re-run Hybrid Configuration wizard to see if messages from O365 can be treated as internal messages.

    If you have any questions, please feel free to contact me.