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I am trying to figure out SSH port forwarding and have not found success from looking at different questions and tutorials, it seems that everything I have seen is just a little different than my situation and I can't quite figure out how to apply it to mine.

I am running an application (A) from a Windows machine in an internal network (22.22.22.xx). This application must be hosted on this network. I also have a Linux SSH client/server (S) on a machine that has a network adapter card for the (22.22.22.xx) network as well as one for the (11.11.11.xx) network. I have an application client (C) running on Windows that has access to the SSH client but does not have access to the (22.22.22.xx) network therefore cannot access A directly. The set up is displayed below.

network setup diagram

I am trying to set up port forwarding from the SSH server so that the application client can reach the application server.

So far, I have been able to get local port forwarding working using PuTTY on the application client. I used this command (entered on PuTTY's UI):

ssh -L 8888:22.22.22.5:5555 [email protected]

From here I am able to go to localhost:8888 on 'C' and am tunneled through 'S' to reach the page being served on 'A'. However, in a perfect world, I would like to not have to open and run PuTTY on the client every time to access the page.

So, I am trying to find a way to set up remote port forwarding to forward a port, say 4444, on 'S' to 'A'. So that from 'C' I could simply go to 11.11.11.4:4444 and I am tunneled into 22.22.22.5:5555.

So far, I have tried running this on the command line in 'S': 

ssh -R 4444:22.22.22.5:5555 user@localhost -o GatewayPorts=yes

When I ran this, it looked like I ssh-ed right back into the machine, I entered the credentials and tried going to 11.11.11.4:4444 from the client and I was not directed to the server. I also tried running this command (but from PuTTY) on 'A':

ssh -R 4444:localhost:5555 [email protected] -o GatewayPorts=yes

From this I got a 'Remote port forwarding failed' message in the PuTTY event log.

I feel like I am very close to the solution and just have something confused in my commands or I am way off and don't understand what is going on at all.

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You don't want a remote/reverse forwarding, although with the local version (your first example) there would be little difference, except it needs configuration on the server. The option GatewayPorts=yes is for the ssh server, not for the ssh client.

Try on the server S

ssh -g -L 4444:22.22.22.5:5555 user@localhost
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  • Hm that seems like it makes sense, but when I tried it, I ssh-ed back into the server S, entered the credentials, and when I tried to connect to 11.11.11.4:4444 from the client I got a connection timeout, running 'netstat -a -n' from the server S I see: '127.0.0.1:22 - 127.0.0.1:40800 - ESTABLISHED', 127.0.0.1:40800 - 127.0.0.1:22 - ESTABLISHED', and ':::4444 - ::: - LISTEN'
    – Jtt3mr
    Aug 22, 2018 at 18:00
  • If you get a connection timeout and not connection refused, a firewall is blocking your connection. You could add the output from netstat to the question.
    – RalfFriedl
    Aug 22, 2018 at 18:05
  • Would that be the firewall of the ssh server or of the application server?
    – Jtt3mr
    Aug 22, 2018 at 18:10
  • On the SSH server, 'S'. The application server accepts connections on port 5555.
    – RalfFriedl
    Aug 22, 2018 at 18:13
  • Running netstat -tuplen on the SSH server gives me: tcp -- 0.0.0.0:4444 -- 0.0.0.0 -- LISTEN -- ssh So that would mean that the SSH process is listening on that port and not being blocked by firewall, correct?
    – Jtt3mr
    Aug 22, 2018 at 18:23

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