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Office365 for Notifications

ThomasRandolph

I have been using Office 365 for email notifications and it has worked up until a few months ago. My fault for not noticing sooner. I have the hostname set as a DNS hostname of smtp.office365.com. My Admin notification logs says SASL authentication Failed; server smtp.office365.com. I noticed that in the settings on Office 365 it says for smtp you need to use STARTTLS on port 587. The setting in the UTM only has a checkbox for TLS. Not sure what the difference is or if that is even the issue. I have it checked and using port 587. I can login with the account I'm using for the notifications to send and receive email from the browser, so I know the account works and it worked up until April. Any thoughts??



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  • 0

    Ok. So I re-entered the Office365 login credentials again, I tried this before, but now messages are flowing again. I did not change anything. I will keep an eye on it to see if it stops again.

  • 0 in reply to ThomasRandolph

    STARTTLS is a command given by the sending MTA after having established a connection on port 25 or port 587.  That check box for TLS is normally used to establish a secure connection on port 465.  I've not tried with it checked for port 587, but it's interesting to note that it works.  Even then, I suspect that the sender will give the STARTTLS command so that there will be an encrypted tunnel in an encrypted tunnel - can anyone confirm that?

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
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  • 0 in reply to ThomasRandolph

    STARTTLS is a command given by the sending MTA after having established a connection on port 25 or port 587.  That check box for TLS is normally used to establish a secure connection on port 465.  I've not tried with it checked for port 587, but it's interesting to note that it works.  Even then, I suspect that the sender will give the STARTTLS command so that there will be an encrypted tunnel in an encrypted tunnel - can anyone confirm that?

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
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