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I currently have this situation:

I have three machines. Call them:

  1. host-client: Windows 7 running the OpenSSH 6.0p1 client under Cygwin
  2. host-ssh-jump-server: Windows 7 running the OpenSSH 6.0p1 server under Cygwin
  3. host-server: Debian 8.9 running the OpenSSH 6.7p1 server, and running an http server on port 8080

host-client opens a SOCKS5 proxy as follows:

ssh -D localhost:1080 -N my-username@host-ssh-jump-server

On host-client, the web browser is configured to use a SOCKS5 proxy at localhost:1080.

The user browses to the web server running on host-server from host-client by entering the following URL into the browser:

http://host-server:8080

The problem is that the connection between host-client and host-server is unencrypted on the hop between host-ssh-jump-server and host-server.

At this moment, getting HTTPS running on host-server is not an option. I need a stopgap. I need to extend the SSH tunnel all the way to host-server.

To minimize user disruption, I would like to do this with these constraints:

  • Don't change the SOCKS5 proxy they create on host-client.
  • Don't change the URL they use to browse to host-server, except possibly for the port number.
  • Other (unrelated) applications traverse the SOCKS5 proxy. They must not be disrupted.
  • Any new tunnels that would be created would need to have the listening port be bound to localhost for security.

How may I do this, or is it not possible?

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ssh -L localhost:1080:localhost:1080 my-username@host-ssh-jump-server -t 'ssh -N -D localhost:1080 root@host-server'
  • Can you be a little more specific with your detail, consider adding some reference and proof supporting what you state. – Pimp Juice IT Sep 8 '17 at 18:37

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