Hello Jon,
If I were troubleshooting this, I would start with looking at logs on your utility server that runs sipserver and stunnel. Just see if you are getting connections from the machines in question at all?
If they are connecting, then you could try and get a traffic dump between stunnel and sipserver just to see the conversation that the two are having. sip2 is fairly easy to understand with just a text dump of the conversation. I like to collect packet dumps with tcpdump and then view them on my local machine with Wireshark. There is a follow stream option that shows you one conversation and can decode it.
You could also have someone on the site run the sip testing tool and try to emulate the self checks, but that might be harder to setup if you use stunnel.
Josh