We utilize Engine Hosting to host our Helpspot installation. And we maintain our own Exchange server in house. How are those two thing related you might ask.
While attempting to limit spam traffic through our server, we have enabled connection filtering. Only allowing SMTP traffic from our spam filtering service. Because Helpspot creates a direct SMTP connection send out email, we can no longer send email from within Helpspot.
I believe I need to isolate the IP address from which the Helpspot generated email is originating. Then I could add that IP address to my connection filter and everything should work. This is not as easy as it sounds because of the hosted installed via Engine Hosting. I have added the public IP address where our installation is running, the same IP I would use to access the SQL database, etc. That did not resolve the problem.
To troubleshoot the situation I turned off connection filtering and sent a test email from within the Helpspot setup and from a fictional ticket. I was able to grab the IP address in the header of those successful test messages. That should be the originating IP address. But, when I re-enable connection filtering with that IP address as an allowed sender, it still doesn’t work.
There seems to be a mysterious 1st source IP address that is still being blocked. Anyone have any ideas on where to look next?