Forwarding Email from Exchange 2019 not working

Question

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!

LuCar Toni · Accepted Answer

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.

Fred_B · Answer

A *.gmail.com send connector will take precedence over * You can also set the priority cost lower. 
 Microsoft Docs: 
 The Send connector that's used to route messages to a recipient is selected during the routing resolution phase of message categorization. The Send connector whose address space most closely matches the recipient's email address, and whose priority value is lowest is selected. 
 https://docs.microsoft.com/en-us/exchange/mail-flow/connectors/send-connectors?view=exchserver-2019

Forwarding Email from Exchange 2019 not working

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