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Can't get email notifications to work.

psykix

Anyone who can help me figure out why my email notifications won't work?

I'm using the same email config that I use on other servers and they work just fine.

I'm using Microsoft hosted Exchange, and I am using :-

Mail Server : smtp.office365.com Port : 587

Username my usual

Password my usual

Connection/Security (I've tried all options!)

Certificate - I've tried Appliance Certificate and None

I get an error saying failed to connect to mail server. Do I need to create a rule or something? I have the Webfilter off and I have the Application filter set to Allow All, but I also set that to None too just in case.



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    I'm getting a similar error and opened a support ticket. I found two problems:

    1. Firstly the DNS server I was using couldn't resolve smtp.office365.com so I did an nslookup and just used the IP, that allowed me to connect. I switched the XGs primary DNS to 8.8.8.8 and now all of a sudden it seems it can resolve the FQDN (weird). But I could now connect to office 365 via port 587 with authentication using STARTTLS
    2. Secondly, a new problem arose is that the sending would fail because of the following error "Authentication method mismatch. Please confirm the authentication method support for LOGIN or PLAIN on the mail server".

    I tried anything and everything available to me to try and get around this problem both on Office 365 and on the XG. I cannot seem to enable PLAIN method on Office 365 but all evidence points to that the LOGIN method is supported. I found in a Cyberoam thread that they had to physically change the authentication method in a Cyberoam product found here: https://www.redmine.org/boards/2/topics/38755

    I believe that the method being used by Sophos for this Notifications section is PLAIN only and the error message does not match what is actually occurring. I am awaiting response from Support to see what's happening under the hood here. As soon as I know an answer I'll update my comment on this thread.

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    I'm getting a similar error and opened a support ticket. I found two problems:

    1. Firstly the DNS server I was using couldn't resolve smtp.office365.com so I did an nslookup and just used the IP, that allowed me to connect. I switched the XGs primary DNS to 8.8.8.8 and now all of a sudden it seems it can resolve the FQDN (weird). But I could now connect to office 365 via port 587 with authentication using STARTTLS
    2. Secondly, a new problem arose is that the sending would fail because of the following error "Authentication method mismatch. Please confirm the authentication method support for LOGIN or PLAIN on the mail server".

    I tried anything and everything available to me to try and get around this problem both on Office 365 and on the XG. I cannot seem to enable PLAIN method on Office 365 but all evidence points to that the LOGIN method is supported. I found in a Cyberoam thread that they had to physically change the authentication method in a Cyberoam product found here: https://www.redmine.org/boards/2/topics/38755

    I believe that the method being used by Sophos for this Notifications section is PLAIN only and the error message does not match what is actually occurring. I am awaiting response from Support to see what's happening under the hood here. As soon as I know an answer I'll update my comment on this thread.

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