Opened new post to be more specific on this topic. I have servers that are already interconnected via SSH tunnels and I can tunnel anything TCP without a problem and it works great. Since BTSync uses UDP, not TCP, I had to figure out how to tunnel UDP. Well, I got the UDP tunneling working by using Zebedee which is wrapping the UDP inside TCP. I made some tests and verified the communication. I also am dumping the data and can see some BTSync data arriving. However, somehow BTSync just doesn't care. I configure to a specific port for BTSync to use, but wonder if it needs something besides that custom port. I probably won't bother continuing this as it seems to be more complicated than it's worth. I'm forced to open FW UDP ports. I know that's better performance, but I was less concerned about that. This was for experimentation but needed to tunnel UDP for different purpose anyway so thought to include BTSync in that test. Agonizing details: To outline, here's what I have, making up port numbers: ServerA and ClientA are the same box just either acting as a server or as a Client. ServerB and ClientB are another box, same story. ClientA BTSync -> 127.0.0.2 : 2001 ClientA Zebedee -> 127.0.0.1 2002 ClientA SSH tunnel -> ServerB : 22 -> 127.0.0.1 : 2000 ServerB Zebedee -> 127.0.0.2 : 3000 ServerB BTSync ClientB BTSync -> 127.0.0.2 : 2001 ClientB Zebedee -> 127.0.0.1 2002 ClientB SSH tunnel -> ServerA : 22 -> 127.0.0.1 : 2000 ServerA Zebedee -> 127.0.0.2 : 3000 ServerA BTSync ServerA has SSH service on port 22 ServerA has Zebedee service listening in TCP/UDP mode on port 2000. ServerA has BTSync listening on UDP 3000. ServerB has SSH service on port 22 ServerB has Zebedee service listening in TCP/UDP mode on port 2000. ServerB has BTSync listening on UDP 3000. Starting at the basics, both servers have SSH connections to each other. Both SSH connections have client to server TCP tunnel where locally 127.0.0.1 : 2002 tunnels to the other server's 127.0.0.1 : 2000 which is the Zebedee service. Then, each server's Zebedee service is configured to accept connections on port 2000, and allows TCP and UDP redirection to 127.0.0.2 : 3000 which is the BTSync service. It seemed that if I used just 127.0.0.1 in BTSync, it almost fooled itself in thinking it's syncing with itself. But by using something like 127.0.0.2, or .3, etc it seemed to at least try to make the connections and data went.. but again somehow it did not care or maybe somehow it did not reach the other side all the way to BTSync.