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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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  • I dont know, what Microsoft Supports. They moved to MFA a while ago. You find the documentation on Microsoft Websites. Essentially it is not broken. It is simply a missmatch between two vendors. 

    Most customers moved to Central Alerting and do not use Email Alerting anymore. (Why should you send a Email from the firewall, if you could do this from Central?). 

    If you have a device to send a notification, you could send this directly. This would basically mean to enter the credentials on each and every device, if you want to authenticated on a centralized manner, but you could do this by using the MTA itself. Then send the Email via Port25 to Microsoft365. 

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