Auto initializing SSH Remote Tunnel

SSH is so incredibly useful

I often find SSH tunnels absolutely indispensable in my line of work for multiple reasons including secure proxies (tunneling) over insecure connections and connecting computers and programs together over difficult network setups involving NATs and firewalls.

One such example of this I ran into recently is that I have a server machine (hereby called “the client”) that I wanted to make sure I have access to no matter where it is. For this I created an auto initializing SSH remote port tunnel to a server with a static IP Address (hereby called “the proxy server”) which attempts to keep itself open when there is problems.

The first step of this was to create the following bash script on the client that utilizes the OpenSSH’s client to connect to an OpenSSH server on the proxy server for tunneling:

#!/bin/bash
for ((;;)) #Infinite loop to keep the tunnel open
do
	ssh USERNAME@PROXYSERVER -o ExitOnForwardFailure=yes -o TCPKeepAlive=yes -o ServerAliveCountMax=2 -o ServerAliveInterval=10 -N -R PROXYPORT:localhost:22 &>> TUNNEL_LOG #Create the SSH tunnel
	echo "Restarting: " `date` >> TUNNEL_LOG #Write to the log file "TUNNEL_LOG" whenever a restart is attempted
	sleep 1 #Wait 1 second in between connection attempts
done

The parts of the command that create the SSH tunnel are as follows:

Part of Command	Description
ssh	The OpenSSH client application
USERNAME@PROXYSERVER	The proxy server and username on said server to connect to
-o ExitOnForwardFailure=yes	Automatically terminate the SSH session if the remote port forward fails
-o TCPKeepAlive=yes -o ServerAliveCountMax=2 -o ServerAliveInterval=10	Make sure the SSH connection is working, and if not, reinitialize it. The connection fails if server keepalive packets that are sent every 10 seconds are not received twice in a row, or if TCP protocol keepalive fails
-N	“Do not execute a remote command. This is useful for just forwarding ports” (This means no interactive shell is run)
-R PROXYPORT:localhost:22	Establish a port of PROXYPORT on the proxy server that sends all data to port 22 (ssh) on the client (localhost)
&>> TUNNEL_LOG	Send all output from both stdin and stderr to the log file “TUNNEL_LOG”

For this to work, you will need to set up public key authentication between the client and utilized user on the proxy server. To do this, you have to run “ssh-keygen” on the client. When it has finished, you must copy the contents of your public key file (most likely at “~/.ssh/id_rsa.pub”) to the “~/.ssh/authorized_keys” file on the user account you are logging into on the proxy server. You will also have to log into this account at least once from the client so the proxy server’s information is in the client’s “known_hosts” file.

For security reasons you may want the user on the proxy server to have a nologin shell set since it is only being used for tunneling, and the above mentioned public key will allow access without a password.

For network access reasons, it might also be worth it to have the proxy port and the ssh port on the proxy server set to commonly accessible ports on all network setups (that a firewall wouldn’t block). Or you may NOT want to have it on common ports for other security reasons :-).

If you want the proxy port on the proxy server accessible from other computers (not only the proxy server), you will have to turn on “GatewayPorts” (set to “yes”) in the proxy server’s sshd config, most likely located at “/etc/ssh/sshd_config”.

The next step is to create a daemon that calls this script. The normal method for this in Linux would be to use inittab. This can be a bit cumbersome though with Linux distributions that use upstart, like Ubuntu, so I just cheated in it and created the following script to initialize a daemon through rc.d:

#!/bin/bash
echo -e '#!/bin/bash\nfor ((;;))\ndo\n  ssh USERNAME@PROXYSERVER -o TCPKeepAlive=yes -o ExitOnForwardFailure=yes -o ServerAliveCountMax=2 -o ServerAliveInterval=10 -N -R PROXYPORT:localhost:22 &>> TUNNEL_LOG\n  echo "Restarting: " `date` >> TUNNEL_LOG\n  sleep 1\ndone' > TUNNEL_SCRIPT_PATH #This creates the above script
echo -e '#!/bin/bash\ncd TUNNEL_SCRIPT_DIRECTORY\n./TUNNEL_SCRIPT_EXECUTABLE &' > /etc/init.d/TUNNEL_SCRIPT_SERVICE_NAME #This creates the init.d daemon script. I have the script set the working path before running the executable so the log file stays in the same directory
chmod u+x TUNNEL_SCRIPT_PATH /etc/init.d/TUNNEL_SCRIPT_SERVICE_NAME #Set all scripts as executable
update-rc.d TUNNEL_SCRIPT_SERVICE_NAME defaults #Set the run levels at which the script runs

OpenSSH RSA Authentication public key file format

Curiosity as always

There are two primary authentication methods for logging onto an SSH server as a user. The first is password based authentication, and the second is public key authentication. The public/private RSA key pair for public key authentication can be created using OpenSSH’s “ssh-keygen” application.

I’m not going to go into the exact method on accomplishing this because instructions can be found on countless other places on the internet. However, I was curious yesterday as to what exactly was in the public key (.pub) files created by ssh-keygen, as the data payload was larger than I expected (2232 bits for a 2048 bit key). I couldn’t find documentation on this ANYWHERE on the internet, so I downloaded the OpenSSH source code and looked at the generation code of the files. The format of the files is as follows:

• The public key files are ASCII based text files with each public key taking up exactly one line.
• Each line is formatted with 2 pieces of data as follows:

  KEY_TYPE DATA_PAYLOAD

• KEY_TYPE is the type of public key, which in our case (and most cases nowadays) is “ssh-rsa”.
• DATA_PAYLOAD contains the actual public key information encoded in base64 with the following format:

Type	Byte length	Name	Description	Default Value
unsigned int	4	KEY_TYPE_LENGTH	Length of the next entry	7
String	See previous	KEY_TYPE	See above	ssh-rsa
unsigned int	4	E_LENGTH	Length of the next entry	3
BigInt	See previous	e	this is the public key exponent in RSA	65537
unsigned int	4	N_LENGTH	Length of the next entry	KEY_BIT_SIZE/8 (optional +1)
BigInt	See previous	n	this is the “modulus for both the public and private keys” in RSA	Key dependent

I also checked putty public key authentication files and they seemed to contain the exact same DATA_PAYLOAD.