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Sophos Email appliances - Authenticated SMTP

I am trying to setup a "authenticated smtp" server that our IMAP/POP users can use as their SMTP server.


Currently they use the SEA appliances as SMTP, which result into their email failing the Mycompany spf rules (we have only dedicated MX servers specified in our SPF rules that are allowed to send email).


I have setup my SMTP server / GroupWise Internet Agent to receive the authenticated smtp transactions. This server then passes (route) the outgoing email via one of the SEA appliances, if its for external users.


This works fine for sending to internal users. When trying to send an email to external users I get the following error

Response: 550 TLS negotiation failure


I have added the new server as an "internal mail host".


I then even tried adding it to "Trusted Relays" and "Mail Delivery Servers" (which I think should not be necessary). It still failed with the same error.


Any advice or anything that I am missing?

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  • FormerMember
    0 FormerMember


    Apologies for the inconvenience caused. 

    Is there any upstream firewall that is scanning traffic from the email appliance? 

    Do you have TLS settings configured on the email appliance for outgoing emails?