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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. 

    Jump to answer
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  • 0

    Hi all,

    We found some information, which we cannot test, but seems like, Microsoft did some changes in On premise Exchange. Feel free to test it and report back, if this solves your problem.

    https://techcommunity.microsoft.com/t5/exchange-team-blog/sender-rewriting-scheme-upcoming-changes/ba-p/2632829

    2. Change in rewriting for SMTP/mailbox forwarding

    We are further consolidating our rewriting for message forwarding. Not all forwarded messages are rewritten using SRS today. Messages forwarded with SMTP or mailbox forwarding have their P1 Mail From address replaced with the forwarding mailbox address. This will change to using SRS rewriting instead.

    This is a behavior change that may result in some disruptions. For one, SRS does not rewrite messages destined for on-premises while the current rewriting process does. This could cause forwarded messages sent to or via on-premises to be rejected by the final recipient or a filtering device along the way.  The setting in #1 has been provided to fix this gap and allow messages to still be rewritten after this change in behavior. Update: we will share more information when we start rolling out the change. Our recommendation is that customers routing messages to the Internet via their on-premises servers should proactively enable the new setting on their connectors. You can find out more about SRS here.

    __________________________________________________________________________________________________________________

Reply
  • 0

    Hi all,

    We found some information, which we cannot test, but seems like, Microsoft did some changes in On premise Exchange. Feel free to test it and report back, if this solves your problem.

    https://techcommunity.microsoft.com/t5/exchange-team-blog/sender-rewriting-scheme-upcoming-changes/ba-p/2632829

    2. Change in rewriting for SMTP/mailbox forwarding

    We are further consolidating our rewriting for message forwarding. Not all forwarded messages are rewritten using SRS today. Messages forwarded with SMTP or mailbox forwarding have their P1 Mail From address replaced with the forwarding mailbox address. This will change to using SRS rewriting instead.

    This is a behavior change that may result in some disruptions. For one, SRS does not rewrite messages destined for on-premises while the current rewriting process does. This could cause forwarded messages sent to or via on-premises to be rejected by the final recipient or a filtering device along the way.  The setting in #1 has been provided to fix this gap and allow messages to still be rewritten after this change in behavior. Update: we will share more information when we start rolling out the change. Our recommendation is that customers routing messages to the Internet via their on-premises servers should proactively enable the new setting on their connectors. You can find out more about SRS here.

    __________________________________________________________________________________________________________________

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