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I know of usual HTTP proxys and Socks proxys (Socks 4 / Socks 5 - where the main difference as far as I know is the support for DNS resolution via proxy).

Both variants more or less "pass the data through" in its original form. So if the target site is HTTPS encrypted, of course the connection will be encrypted. Same goes for Socks proxys.

However what I would like to do is to encrypt the communication between the proxy server and the client regardless whether the communication between the proxy server and the target server is secured or not.

The only software that comes to my mind which does this is TOR (The onion router), however it does much more and is not really what I want.

I am aware of VPN solutions. However I would prefer something which does not need to be configured on that layer of the OS (no extra devices, drivers, software etc.). It would be good if it would be supported by major browsers out of the box.

You may thing of the use case of sitting on a very insecure network (for example a public WIFI) where everyone can sniff your traffic.

You want to securely (however only securely from that wifi) visit a webpage which is only reachable via insecure HTTP.

Now you can connect to the proxy securly and futher insecurly to the website, however this part is out of the insecure wifi.

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up vote 1 down vote accepted

Squid proxy server supports incoming proxy connections on an SSL encrypted port with the https_port directive.

However, support in browsers is limited currently. You can use a proxy.pac script with Chrome which can contain an https server for a proxy. This is pretty easy to setup, and there are many howtos on the net.

If your proxy server supports ssh, then you could just use an ssh tunnel for the first part. Suppose your proxy server listens on port 3128, then this will establish a tunnel to the proxy:

 ssh -L3128: [proxyserver]

Then all you need do is configure your browser to point to a proxy server on and you'll use your remote proxy with the first part encrypted. The above command is command line, but putty and all other ssh clients support this, you just need to figure out the configuration.

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the ssh tunnel is what i am actually doing at the moment ;) hwoever squid looks promising! –  Joe Hopfgartner Dec 6 '12 at 13:33
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Consider PPTP VPN. It can be connected from any modern OS without any additional software. I use it with Windows, Linux and iOS. There is a dozen of PPTP VPN providers such as 'Proxpn'. And it is not so hard to start the PPTP server by yourself.

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