Problem with notifications and outlook365 exchange hosting

  • I'm unable to get notifications working from my pfSense box to my email via my hosted Exchange SMTP over on Outlook365.

    I currently have several other hardware devices all using email notifications today successfully.  These include an alarm panel and an automation controller.

    I've used the standard Outlook 365 settings of:

    server -
    port - 587
    ssl/tls - checked

    With pfSense it refuses to send and throws an error in the log:
    php: /system_advanced_notifications.php: Could not send the message to XXX – Error: could not connect to the host "": ??

    I've tried 25 and 465 as well with and without ssl/tls and all the permutations throw the same error.

    Any suggestions?


  • Any luck with this?  I'm having the exact same problem.  Works fine with gmail but not hosted outlook.

  • Nope still not working and still having the same error.  The funny thing is I've got the setup working on a couple wireless APs, a BSD based home automation appliance, and my home alarm system.  They all handle the SMTP notification just fine with the exact same settings.

  • Did you ever resolve this issue? I'm having the same problem with a Postfix server.,60874.0.html