Using End to end Encryption on Exchange Hybrid mode.

Question

Using End to end Encryption on Exchange Hybrid mode.

Waleed Waleed 0

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.

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Answer 1

Anonymous

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:

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”.
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.
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.

Waleed Waleed 0 Reputation points

2024-04-23T11:15:32.4833333+00:00

hi Noah,

Thank you for your answer,

I checked the Accepted domains and the CloudServicesMailEnabled:

they are already like this.
what should I do?
Anonymous

2024-04-25T10:57:39.34+00:00
Hi,

There's one more important thing to confirm if all that emails from O365 send to on-premises shown as external.

If no, this issue may be caused by the rule. If yes, you could refer to the followings next as you have checked the mentioned above:

Check if the Remote Domain with TrustedMailOutboundEnabled as True.

Check if the receive connector TlsDomainCapabilities is AcceptCloudServicesMail or AcceptOorgProtocol.

Is your version Exchange 2010?

If no, check is there an Accepted Domain maching the sender. If not, you can follow the step in the yes section below.

If yes, check if remote domain maching the sender and attribute TrustedMailInboundEnabled is True.

For more information you can refer to: Demystifying and troubleshooting hybrid mail flow: when is a message internal? - Microsoft Community Hub
Anonymous

2024-04-30T10:06:04.26+00:00

Just checking in to see if above information was helpful.

If the issue has been resolved, please mark the helpful replies as answers.

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Using End to end Encryption on Exchange Hybrid mode.

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