Woops, starting with the forwarded ports... 192.168.1.100 UDP/5353 -> VM UDP/53 192.168.1.100 TCP/5353 -> VM TCP/53 192.168.1.100 TCP/5667 -> VM TCP/5667 [...] I am able to get DNS replies using both of dig @192.168.1.100 -p 5353 google.com A dig @192.168.1.100 -p 5353 google.com A +tcp But dig times out when I try to use dig @192.168.1.100 -p 53 google.com A The stunnel server log is here: http://sprunge.us/deLY The stunnel client log is here: http://sprunge.us/ScAC Why this is happening? I notice the three connection attempts which seems like it's relevant to the connection resets.