SSH Tunnel setup–for Windows users

By | June 25, 2014

“What’s an SSH tunnel?” you ask? In layman’s terms, it’s a way for you to take one PC, and pipe all its network traffic through another PC before it gets out to the internet. So what this means is that if, oh, somewhere were to say, monitor the traffic from your PC all they’d see is one pipe open to one endpoint transferring data. Nothing more, nothing less.

Sound like something you might like to utilize? Thought so ;)

To do most of the installation and procurement of tools we’re going to use my favorite: chocolatey. So if you don’t have it, go grab it now. I started with this article:–encrypt-your-web-browsing-session-with-an-ssh-socks-proxy

within that page, there’s a link to setting up the server portion, which you’ll put on the PC you want to do all the Internet chatting for you. This one:–set-up-a-personal-home-ssh-server

thanks to chocolatey, to install cygwin we just run

cinst cygwin

at a command prompt. When cygwin installs via chocolatey, it does miss the installation of openssh. So to do this, you next need to fire off:

cygwinsetup –q –P openssh

from the cygwin installation directory. This installs open SSH in to cygwin in “quiet” mode.

Now that that’s done, you can move forward with the rest of the things in that article. One of the more important things to remember when setting up the server is to set it up with a port that you can access freely from your “client” computers. In other words if where you’re at blocks things like telnet, you don’t want to choose 23. Stuff like that.

A quick way to make sure things are working is to observe your IP before and after setting up the SSH tunnel on the client side. Bing makes this very easy.

Now let’s make this technique usable.

When you log in to your PC, let’s fire up the tunnel on first start. Quick & easy with a cygwin batch file.

Avoid the login prompt when you tunnel to the server PC with this script.

And finally, switch quickly and easily between proxy settings that utilize your SSH and a local, direct connection (intranet access, perhaps?) with this awesome free tool.

Enjoy your freedom!