Email Setup In Sage 100 - Question On Connectivity To The SMTP Server

I have completed the email/SMTP setup on our Sage server.  From a security standpoint, we require IP addresses to be allowed through our firewall and to be whitelisted on our SMTP servers.  This has also been completed for our Sage server.  In testing the email/SMTP setup, I find that the test is successful if I run the test directly from the Sage server, and it fails if I run the test from a Terminal Server that has been set up with the Sage workstation client.  So, does the email/SMTP request initiate with the Sage server IP address or from the IP of the workstation initiating the request/process generating the email/SMTP..