OK, I'm resurrecting this thread because I'd really like to get this to work. So first off, if I set the "Listen on IP" (aka the "accept" line of the stunnel.conf file) for an stunnel config to anything except the pfsense box, stunnel won't bind properly. So I changed the tunnel to basically accept the IP address of the pfSense box. Here's an example of a tunnel I set up on the pfSense box:
Listen on IP: 192.168.0.1
Listen on Port: 999
Redirects to IP: biteme.someremotehost.com
Redirects to Port: 2029
In this example, biteme.someremotehost.com is a DirectConnect hub. Now I go to my client PC on the LAN (which is not running any sort of stunnel client) and set up a connection in my DirectConnect client to point to 192.168.0.1:999. When I do that, the DC client sits there at:
*** Connecting to 192.168.0.1:999...
*** Connected
In the pfSense logs I get:
stunnel: LOG5[12263:134766080]: DirectConnect accepted connection from 192.168.0.22:3393
stunnel: LOG3[12263:134766080]: SSL_accept: Peer suddenly disconnected
And that's it. The DC client just kinda sits there for a while and nothing happens.
Does anyone have any ideas? Perhaps I'm configuring/using this setup incorrectly?