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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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  • Yeah I get that... I was asking what Microsoft requires.  I guess we can drop this -- still amazing to me that this hasn't been fixed given it's something supported (apparently) on the most basic IOT type devices, printers, etc. nowadays.

    CTO, Convergent Information Security Solutions, LLC

    https://www.convergesecurity.com

    Advice given as posted on this forum does not construe a support relationship or other relationship with Convergent Information Security Solutions, LLC or its subsidiaries.  Use the advice given at your own risk.

  • 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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  • One reason is that as a customer you can't configure your own alerts and have to sit and work with a partner to tune them and then always go through someone else to make changes.

  • Actually you can configure your own alerts in Central... unless you are talking about a scenario where you are using a MSP and want your own alerts (which we configure ourselves for customers as needed -- we also are an MSP) and they don't give you access to Central admin on your account, etc.

    CTO, Convergent Information Security Solutions, LLC

    https://www.convergesecurity.com

    Advice given as posted on this forum does not construe a support relationship or other relationship with Convergent Information Security Solutions, LLC or its subsidiaries.  Use the advice given at your own risk.

  • Yes, when using an MSP.  I have access to Central Admin but the alerts section is locked and we don't have access and were told we can't get access because that would require them to unlock that section for all customers and would create issues as far as how they manage alerts.

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