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Are Authenticated SMTP Notifications still broken in Sophos Firewall?

I know this was an issue many years ago -- now I've run across a customer that we want to set this up for (they got bought out, and the parent company migrated all their email to O365, and the folks I deal with have no access to the admin controls in O365) -- and no matter what I do, I cannot send firewall notifications out via a configured O365 relay (they require authentication).  I do have other customers that I do manage, and in those cases we helped them setup relays (by static IP) that did not require authentication, and that works.

I suspect that (somehow, it's been a very long time) that Sophos has not fixed this issue yet (if you use authentication, you have to have TLS/StartTLS enabled with O365) with Sophos Firewall.  IIRC, it had to do with them using MD5 which Microsoft rejects. I will be starting a support case on this, but checking here first to see if any of you have had a different experience recently.



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  • It was not implemented. Basically PLAIN Authentication is fine for most SMTP but not Microsoft. You could ask Microsoft to support Plain Authentication as well. But at this point, SFOS does not support the way, microsoft authenticate and microsoft does not support the way, the firewall works. 

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