Kaseya Community

How to troubleshoot mail not sending?

  • We noticed earlier this week that we are suddenly no longer getting email alerts from our Kaseya server.

    It is a Server 2003 box sitting on the same domain as our Server 2003/Exchange 2007 server, and has not been upgraded to K2 yet.

    We've spent part of yesterday and most of today troubleshooting it. Thus far, we have discovered the the mail simply stacks up in the outgoing que, but we don't know why it won't send. Sending a message yields only Event 4007 in the event logs:
    Message delivery to the host 'myipaddress' failed while delivering to the remote domain 'mydomain.com' for the following reason: The remote SMTP service rejected AUTH negotiation.
    The SMTP verb which caused the error is 'AUTH'. The response from the remote server is '250-mail.mydomain.int Hello [192.168.1.1]
    250-SIZE
    250-PIPELINING
    250-DSN
    250-ENHANCEDSTATUSCOD'.

    We're stumped, and we're not even sure if this is a Kaseya issue or not, but we suspect not. Any help? Run across something similar?

    Thanks!

    Legacy Forum Name: How to troubleshoot mail not sending?,
    Legacy Posted By Username: danielm
  • Sounds like you are requiring authentication to relay through your server. By default Kaseya does not do anything with authentication, so I would find a way to whitelist your Kaseya server to allow it to send freely.

    Legacy Forum Name: How-To,
    Legacy Posted By Username: CCDave
  • CCDave
    Sounds like you are requiring authentication to relay through your server. By default Kaseya does not do anything with authentication, so I would find a way to whitelist your Kaseya server to allow it to send freely.


    Cool. I whitelisted it, both using FQDN and IP. Interestingly, it looks like when I reboot the KServer, it will send the mail for about twelve hours until it starts stacking up again.

    Pretty definitively a server issue and not related to Kaseya at this point, but if anybody has any thoughts (this is the first time we've used Virtual SMTP) I would appreciate more suggestions.

    Thanks!

    Legacy Forum Name: How-To,
    Legacy Posted By Username: danielm