AI> When I poll 153/757.2 like this from 153/757
 AI> I get a TLS error. At the remote side
 AI> (153/757.2) I see this..

 AI> BINKPS connection accepted from:
 AI> 2600:3c04::f03c:92ff:fe69:8db0 port 47496
 AI> BINKPS JavaScript service thread started
 AI> BINKPS TLS ERROR 'Recieved TLS alert
 AI> message: Handshake failure' (-15) setting
 AI> session active

i think it is a problem with the TLS library binkit is using.

 AI> I'm currently using a self signed cert on
 AI> 153/757.2, could that be the problem?

self-signed should be fine, but their might be other problems with the cert.
have you tried another one?