Contain me if you can – the art of tunneling

This blog post briefly explains the basics of SSH tunneling and dives into the detail of reverse tunneling. If you are already familiar with all these concepts, this might be a boring read. If you heard “reverse tunneling” for the first time now, you’re about to discover the dark side of a network administrator’s might.

SSH basics

SSH (secure shell) is a tool to connect to a remote computer. In this blog post, the remote computer is always “the server” and your local computer is “the notebook”. That’s just nomenclature, in reality, each computer (or “endpoint”, which is a misleading term, as we will see) can be any device you want, as long as “the server” runs a SSH server daemon and “the notebook” can run a SSH client program. Both computers can live in different local area networks (LAN). As long as it is possible to send network packets to the specific port the SSH server daemon listens to and you have some means to authenticate on the server, you have free reign over both LANs by utilizing SSH tunnels.

The trick to bypass the remote LAN firewall is to have a port forwarded to the server. This allows you to access the server’s port 22 by sending packets to the internet gateway’s worldwide address on a port of your choice, maybe 333. So the forwarding rule is:

gateway:333 -> server:22

If you can comprehend this, you’ve basically grasped the whole foundation of SSH tunneling, even if it had nothing to do with SSH at all.

SSH tunneling basics

Now that we have a connection to the server, we can enjoy the fun of forward tunneling. You didn’t just connect to the server, you opened up every computer in the remote LAN for direct access. By using the SSH connection, you can define a SSH tunnel to connect to another computer in the remote LAN by saying:

localhost:8000 -> another:80

This is what you give your SSH client, but what actually happens is:

localhost:8000 -> gateway:333 -> server:22 -> another:80

You open a local network port (8000) on your notebook that uses your SSH connection over the gateway and the server to send packets to the “another” computer in the remote LAN. Every byte you send to your port 8000 will be sent to port 80 of the “another” computer. Every byte it answers will be relayed all the way back to your client, speaking to your local port 8000. For your client, it will look as if port 80 of “another” and port 8000 of your notebook are the same thing (if you don’t mind a small delay). And the best thing: Your client can be anywhere in your local LAN. Given the right configuration, “notebook2” in your LAN can speak with port 80 of “another” in the remote LAN by using your SSH tunnel. If you’ve ever played the computer game “Portal”, SSH tunneling is like wielding the portal gun in networks, but with unlimited portals at the same time. Yes, you can have many SSH tunnels open at once. That’s pretty neat and powerful, but it’s essentially still only half of the story.

SSH reverse tunneling basics

What you can also do is to open a network port on the server that acts like a portal in the other direction. You probably noticed the arrows in the tunnel descriptions above. The arrows really give a direction. If your tunnel is

localhost:8000 -> another:80

you can send packets from you to another (and receive their answer), but it doesn’t work the other way around. The software listening at another:80 could not initiate a data transfer to localhost:8000 on its own. So SSH tunnels always have a direction, even if the answers flow back. It’s like a door phone: You, inside the building, can initiate a call to the entrance door phone at any time. The guest in front of the door can speak back, but is not able to “call you back” once you hang up. He can not strike up a conversation with you over the phone. (In reality he still has the doorbell to annoy you. Luckily, the doorbell is missing in networking.)

SSH reverse tunnels change the direction of your tunnels to do exactly that: Give somebody on the remote LAN the ability to send network packets to the server that will get “teleported” into your local LAN. Let’s try this:

localhost:8070 <- server:8080

If you set up a reverse tunnel, any computer that can send packets to the port 8080 on the server will in fact speak with your notebook on port 8070. This is true for the server itself, any computer in the remote LAN and any computer with a SSH tunnel to port 8080 on the server. Yes, you’ve just discovered that you can send a data packet from your LAN to the remote LAN and have it reverse tunneled to a third LAN. And if you haven’t thought about it yet: Every “endpoint” in your three-LAN hop can be a portal to yet another hop, with or without your knowledge. This is why “endpoint” is misleading: It implies an “end” to the data transfer. That might just be your perception of the situation. Every endpoint can be another portal until it’s portals all the way down.

SSH reverse tunneling fun

You can use this back and forth teleporting of network traffic to create all kinds of complexity.

But in our case, we want to use our new might for something fun. Let’s imagine the following scenario:

  • On your notebook, you can start a SSH connection to the server. You can open forward and reverse tunnels.
  • On your notebook, you run a VNC (Virtual Network Computing) server. VNC is basically a simple remote desktop technology that lets you see the display content of a remote computer and control its keyboard and mouse. You running the server means somebody else can connect to your notebook using a VNC client and control it as if it was local (if you can ignore a small delay).
  • Somebody else (let’s call her Eve), on her notebook, can also start a SSH connection to the server. She can open forward and reverse tunnels.
  • On her notebook, she has a VNC client software installed. She can connect and control VNC server machines.

And now the fun begins:

  • VNC servers typically listen on network port 5900. In the client, this is known as “display 0”, which means that a client connects to the port “display + 5900” on the server machine.
  • Using this knowledge, you create a reverse tunnel for your SSH connection to the server: localhost:5900 <- server:5901. Notice how we changed the port. This is not necessary, but possible.
  • Now, anybody with direct access to your network port 5900 (in your LAN) or access to the network port 5901 on the server (in the remote LAN) can remote control your desktop.
  • Eve creates a forward tunnel for her SSH connection to the server or any other machine in the remote LAN: localhost:5902 -> server:5901. Notice the port change again. Also just a possibility, not a requirement. Notice also that Eve doesn’t need to connect to the same server as you. Her server just needs to be able to initiate a data transfer with the server. This might be through multiple portals that don’t matter in our story.
  • Now, Eve starts her VNC client and lets it connect to localhost:2 (2 is the display number that gets resolved to local port 5902).
  • Eve can now see your screen, control your inputs and even transfer files (depending on the capabilities of your VNC setup).

This is the point where LAN containment doesn’t really matter anymore. Sure, you cannot reign freely over any machine anywhere, but you can always establish a combination of reverse and forward tunnels to connect two computers as if they were connected by a cable. Which is, in fact, a good analogy to think about SSH tunnels: cables with two different connector types that span between computers.

Wrap up

You are probably aware about the immediate security risks that follow all that complexity. If you want to mitigate some of the risks, have a look at stunnel. It is effectively a more secure (and constrainable) way to create portals between LANs.

And if you just want to have fun: Please be aware that most of the actions here are probably not legal if done without consent of all participants. Stay safe!

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