Sophos Email customers using IP-based mailflow rule connectors must migrate to certificate-based configuration by March 31st. To see if you're affected Click Here.

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New Mailflow setup

Mark Stringer

I see the new Mailflow functionality is appearing in my Cloud Portal as a released feature. In the help it states:

Sophos Mailflow doesn't currently support the following:

What do you mean by it does not support TLS? What elements of the email transmission are not encrypted using TLS connections exactly?

After switching to the Mailflow method from the Gateway method do I also need to:

1. Remove the Bypass Exchange Online Protection in Microsoft 365 rule in O365 Mailflow Rules?

2. Remove the Secure Connector between Microsoft 365 and Sophos Gateway?

Will the new Mailflow method remove the Sophos Banners on my emails when I reply to them as part of the Outbound process?

Thanks,

Mark.



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[edited by: Raphael Alganes at 6:04 AM (GMT -7) on 7 Jun 2023]
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  • +1

    I enabled this recently and had a lot of issues with valid inbound users showing as unverified users due to spf fails because gmail and other common domains don’t designate our custom outlook domain as a valid sender. When Microsoft forwards the email to Sophos, Sophos checks the spf for gmail.com and gmail doesn’t have our outlook domain as a designated sender.

    I also noticed issues with emails going to quarantine on the Microsoft side and bypassing Sophos entirely. The way Microsoft handles redirects to aliases bypasses the forwarding to Sophos. I could see in our message traces in exchange that the emails were being routed to the Sophos connector but when you check for the email in Sophos, a log doesn’t exist. Even when I setup the onmicrosoft.com domain in Sophos Mailflow, I experienced the same issue.

    I opened a ticket with Sophos on this and was informed by support that they haven’t been trained on Mailflow because it’s still in EAP which makes me wonder why I’m being prompted to set it up in Sophos central; I’m not registered for the Mailflow EAP either. Doesn’t seem fully baked at this point and the issue with spf fails and unverified users needs to be addressed before we can migrate fully to Mailflow. I like the idea though and definitely seems more efficient than redirecting MX. Following this thread to see if others have similar issues. 

  • 0 in reply to Caleb Terry

    Thanks for the info Caleb. It sounds like I should maybe hold off on converting for a while then whilst any early issues are fixed. I might try enabling the outbound Gateway option instead and see if that works ok for me. The Mailflow option would be better for us when onboarding new customers though as the fact it means the MX record does not need changed is a big help.

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  • 0 in reply to Caleb Terry

    Thanks for the info Caleb. It sounds like I should maybe hold off on converting for a while then whilst any early issues are fixed. I might try enabling the outbound Gateway option instead and see if that works ok for me. The Mailflow option would be better for us when onboarding new customers though as the fact it means the MX record does not need changed is a big help.

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