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When it not possible to reach a server you want to SSH to directly, you can make use of SSH’s built in capability to chain multiple commands. Suppose you have a network setup like in the image below.

Network overview

Network overview

Firewalls or ACL’s prevent direct access to the ‘web server’ in network #2. In between is a ‘jump host’ in network #1. A ‘jump host’ is a host you can SSH to, and from there reach the next hop. How to SSH to the web server?

You could do this manually:

ssh -l user jump-host

and then from that server:

ssh -l user webserver.dmz

But using the -t switch, you can chain them together like this:

ssh -A -t -l user jump-host \
ssh -A -t -l user webserver.dmz

The -A switch enables forwarding of the ssh-agent. When using key based authentication, you’ll be able to login with typing the certificate’s password only once.

Using this technique, you can also build a SSH tunnel through the jump host:

ssh -A -t -l user jump-host \
-L 8080:localhost:8080 \
ssh -A -t -l user webserver.dmz \
-L 8080:localhost:8080

When you type: http://localhost:8080 in a browser, you are connected over a secure tunnel to the web server in Network #2. Thanks to the chaining of commands, this is now possible.

You can use many chained commands, so this is very flexible.