SMTP Configuration Question

We are using Sage 100.  We have some users that use the workstation app on their local machines and we have some users that connect to a Terminal Services box to run the workstation app.  I recently configured SMTP on the Sage server.  We require firewall rules that allow the IP of systems sending via SMTP to be allowed to get to the SMTP server.  The rule has been put in place to allow the Sage server to access the SMTP server.  What I have found is that if I perform an SMTP test from the Sage server itself, the test passes.  If I perform an SMTP test from the Terminal Services box (and presumably a users local workstation), the test fails.  All that said, my question is as follows:  When functions within Sage are performed that send email via SMTP, does the connection to the SMTP server utilize the IP of the Sage server (where it is configured) or does it utilize the IP of the workstation (the Terminal Services box or a local user workstation)?

Thanks.