Cannot OPENVPN through SSH Tunnel

birtong

Hi,

Sorry to bore you if this is an easy question but I've run out of ideas.

Environment:

Windows 7 64bit client...... PUTTY (0.63) Tunnel..... pfsense 2.x OPENVPN Server

Goal:

Create an OPENVPN environment, inside of an SSH tunnel. I know there is lots of overhead to this but it's the only way I can OPENVPN from my work.

Accomplished:

1. Working PUTTY SSH tunnel from work to pfsense server. I know it's working because I can SSH into my pfsense box and proxy SOCKS connections over the SSH tunnel.

2. Working OPENVPN TCP Client / Server. It work when I go direct to the pfsense box.

PUTTY Tunnel: L1195 localhost:1195

Issue:

When I try to connect OPENVPN through the tunnel by changing destination address to localhost (same port). I get this error:

Tue Aug 12 15:03:58 2014 Attempting to establish TCP connection with [AF_INET]127.0.0.1:1195
Tue Aug 12 15:03:58 2014 TCP connection established with [AF_INET]127.0.0.1:1195
Tue Aug 12 15:03:58 2014 TCPv4_CLIENT link local (bound): [undef]
Tue Aug 12 15:03:58 2014 TCPv4_CLIENT link remote: [AF_INET]127.0.0.1:1195
Tue Aug 12 15:04:58 2014 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Tue Aug 12 15:04:58 2014 TLS Error: TLS handshake failed
Tue Aug 12 15:04:58 2014 Fatal TLS error (check_tls_errors_co), restarting
Tue Aug 12 15:04:58 2014 SIGUSR1[soft,tls-error] received, process restarting

Any ideas?

Thank You,
BG

birtong

Traffic wrote
birtong wroteWhen I try to connect OPENVPN through the tunnel by changing destination address to localhost (same port). I get this error:

Tue Aug 12 15:03:58 2014 Attempting to establish TCP connection with [AF_INET]127.0.0.1:1195
Tue Aug 12 15:03:58 2014 TCP connection established with [AF_INET]127.0.0.1:1195
Localhost 127.0.0.1 is the machine you are sitting at not the remote end ?

I'm using 127.0.0.1 because I've created an SSH tunnel on the local machine. They way other software works, accessing the localhost and tunneled port, causes the traffic to reach the remote server. This is how PUTTY access the remote server via the Tunnel.

Based on other experience, since this post, it seems there is an ip / port / tunnel issue in my set up.

Has anyone done this successfully? I'd like to understand what your OPENVPN config looks like? i.e. do you set local, rport, remote, etc....

Thanks,
BG

maikcat

your putty settings are correct if you connect to pfsense itself...

also accessing localhost AFTER ssh session is up is correct also...

can you post openvpn configs/logs?

Michael.

maikcat

there is a logical problem to what you are trying to do....

if you ssh to pfsense and use redirection of your local (ssh client side) to pfsense (ssh server side)
you will notice that if you telnet to openvpn service port all requests appear to come
from pfsense itself...

so you are trying to create a tunnel from pfsense to ....pfsense?

Michael.