There are no firewalls on either side. The server has two interfaces, one is on the 192.x.x.x range and the other on 10.x.x.x the client only one interface to the 192.x.x.x subnet (as well as the internet). I am assuming that synergy2 doesn't listen on all interfaces so the server was only listening on the 10.x.x.x and the client was trying to connect to 192.x.x.x but as I couldn't find any config options / debug information I couldn't go any further.   If it helps you debug, this