Notifications with Office365 do not work

[Mks]

Hi.

I cannot send notification mails with Office365.

I've tried several options

SMTP over SSL/TLS
opnsense: /system_advanced_notifications.php: Could not send the message to XXXX@XXXX.XX -- Error: could not connect to the host "smtp.office365.com": ??

StartTLS
opnsense: /system_advanced_notifications.php: Could not send the message to XXXX@XXXX.XX -- Error: 504 5.7.4 Unrecognized authentication type [DB6PR0XXXXXXXX.XXXXX.prod.outlook.com]

If found this threas https://forum.pfsense.org/index.php?topic=72015.0 which describes it in more detail but is from 2014.

Anyone solved it without changing manually some congfig lines with possible side effects?

br
Manuel

[marjohn56]

Yes, solved it by using Monit. Takes a bit of setting up, but there are guides around for doing so.

[phoenix]

Hi.

I cannot send notification mails with Office365.

Do you mean you're sending an email to office365 or sending an email via that service (relaying) to another account? Have you used port 25 or 587? I can't imagine why it wouldn't accept it and I have no problems connecting vis STARTTLS on my own mail server using port 25 or 587.

[marjohn56]

Doesn't work for me either, using my office365  account or my Kerio mail server. Actually that's not true, I can get it to work on Kerio but I have to turn on plain authentication.

[fabian]

Doesn't work for me either, using my office365  account or my Kerio mail server. Actually that's not true, I can get it to work on Kerio but I have to turn on plain authentication.

Plain authentication is the way to go when using a TLS encrypted connection...