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Forwarding Email from Exchange 2019 not working

JTK

I have outbound emails filtered through Sophos and in the outbound gateway I have the ip of the firewall.  The client can send emails out normally using outlook.  The issue is when we have a mailbox set up to forward mail to a contact through the recipient / mail flow in the exchange admin center the email gets rejected by Sophos.

This is not an issue with the exchange server as it used to work when filtered through Reflexion. The minute we moved to Sophos Email it started to block any forwarded messages.  Any help would be appreciated.

Thanks!



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  • in reply to Fred_B +1 verified

    This is an intended behavior of Central Email.

    The reason is, Exchange somewhat act ugly in a sense.

    Because if you do a auto forward on the Exchange, Exchange will forward the email in the name of the original sender. Which means, if somebody is sending you a email from @sophos.com Exchange will try to send this email with "FROM: @sophos.com" which of course breaks with a lot of stuff like SFP etc. 

    To prevent this blocking and potential blacklisting of Central IPs, CEMA is blocking the email directly.

    If you press in Outlook "Forward" the user is sending the email in a "nice manner", which means, the original recipient is the new "sender". 

    I cannot comment on "why Exchange is doing this". But we tested this several times and cannot get any way of "admin way" to get this forwarding working. 

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    Something has changed on Email Gateway. I guess autoforward is now threated as relay somhow. I don't see it in the post-delivery queue either.

    In the past I used autoforward rules locally in Outlook. Specific external senders were forwarded also externally. No problem. Just worked.

    Yesterday I had to enable an autoforward on the exchange server mailbox for a certain mailbox and that did not work. I ran into the message that we do not have permission and recipient is relay-eu-central-1.prod.hydra.sophos.com. I enabled bulk sender on the mailbox in Central but the volume is not the issue.

    I removed the server side autoforward and tried with a outlook forward and that now gives the same error message:

    Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept email from certain senders, or another restriction may be preventing delivery.

    The following organization rejected your message: relay-eu-central-1.prod.hydra.sophos.com.

    Thanks,

    Fred

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  • 0

    Something has changed on Email Gateway. I guess autoforward is now threated as relay somhow. I don't see it in the post-delivery queue either.

    In the past I used autoforward rules locally in Outlook. Specific external senders were forwarded also externally. No problem. Just worked.

    Yesterday I had to enable an autoforward on the exchange server mailbox for a certain mailbox and that did not work. I ran into the message that we do not have permission and recipient is relay-eu-central-1.prod.hydra.sophos.com. I enabled bulk sender on the mailbox in Central but the volume is not the issue.

    I removed the server side autoforward and tried with a outlook forward and that now gives the same error message:

    Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept email from certain senders, or another restriction may be preventing delivery.

    The following organization rejected your message: relay-eu-central-1.prod.hydra.sophos.com.

    Thanks,

    Fred

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