The right tool for tunneling SSH through a proxy like Squid, Gauntlet, CacheFlow, Junkbuster, or Apache mod_proxy is Corkscrew. Why? Because the name corkscrew is well chosen, and because the program author introduces himself like this: "My name is Pat Padgett. I'm a dork." In my experience, such laconic people are great programmers.

Most distros have a Corkscrew in a back drawer somewhere; if not, you can pick it up online [1]. The SSH daemon should be running on port 443 on the target server, because many proxies refuse to connect to port 22. Incidentally, binding the SSH daemon to two or more ports simultaneously is not a problem. To do this, you just add another port line to your sshd_config:

[...]
Port 22
Port 443

If you are already running HTTPS on port 443, you can set up SSLH [2] on your server as a last resort. This is an SSH/SSL multiplexer that makes it possible to operate SSH and HTTPS simultaneously on port 443.

If the proxy asks for login credentials, you need to store them in a file. Its name does not matter; I would use, say, /home/charly/.proxy-auth. Then, you can populate the file with data as follows: <Username>:<Password>

Getting Corked

Now you have to talk your SSH client into using Corkscrew. Edit the .ssh/config file in your home directory for this. (If it does not exist, simply create it.) You will be adding two lines:

Host *
ProxyCommand corkscrew <myproxy.example.net> <3128>%h %p /home/<charly>/.proxy-auth

Of course, you need to change <myproxy.example.net> and the port number to suit your local situation. The variables %h and %p pass the parameters from the SSH call to Corkscrew. If you use a server without authentication, you just leave out the path to the username/password file.

Now, it's time for the premiere. The target server I use is a Raspberry Pi, whose sshd listens on port 443. The proxy is a standard Squid. As you can see from Figure 1, the login works fine  – there is nothing to suggest that Corkscrew has a hand in the game, unless someone has access to the proxy logs. You would find the following entry, if you looked:

Figure 1: All done with Corkscrew: perfect remote login on Charly's Raspberry Pi.

"CONNECT 10.0.0.5:443 HTTP/1.0" 200 <[...]>

But, who cares about logs while you're relaxing in a beach bar? Ah, they have WiFi.