When connecting to a possibly hostile network I want to tunnel all traffic from my browser to some proxy I have set up on the Internet.

The obvious way to do this is with a proxy. The problem with that is that the traffic from the browser to the proxy is not encrypted. Even when you browse to secure SSL sites some traffic is being sent in the clear, such as the host name. That’s not so bad, but I want to hide my HTTP traffic too.

Turns out that at least Chrome does support using SSL between the browser and the proxy, but you can’t configure it directly. You have to use Proxy Auto Configuration to point to an HTTPS host:port.

Running OpenVPN is out in this case since I want it to work with everything, including Android and ChromeOS… and Windows (without installing “stuff”). Not that I’ve tried it with Windows yet, but it should work.

For added fun I wanted to authenticate to the proxy using a client certificate, so that I don’t have to worry about remembering or losing passwords.

Before you set off to do the same thing I should warn you that either I haven’t done it quite right or there is a bug in Chrome. If the network has a hickup so that the proxy or the .pac file is unavailable it will fall back to connecting directly. I want it to never fall back. That’s kind of the point.

But all is not in vain. I also set up IPSec with these same certificates. There will be a follow-up post describing how I set this up to tunnel securely with both Chromebook and my phone.

This is what I did (caveat: some of this is from memory. If you find any errors please let me know):

1. Copy easyrsa 2.0 from openvpn sources

This is a set of scripts to manage a CA. We’ll be using this directory/set of scripts both to create a server and client certificates. But only the client certificates will be signed by our own CA.

2. Edit vars file

I like to change KEY_SIZE to 2048, country and other stuff. These will be the defaults when creating certs.

3. Init easyrsa


This is a one-time init. Don’t run this script again.

4. Build the CA for the client certs


5. Copy CA cert to proxy server

scp keys/ca.crt proxy:/etc/proxy-ssl/proxy-ca.crt

6. Build server key and signing request

./build-req proxy.foo.com

7. Get signed server cert

Send keys/proxy.foo.com.csr to your real CA (e.g. cacert.org or Verisign). You’ll get back proxy.foo.com.crt. If you do use cacert.org then make sure that your browser trusts their root by importing it.

8. Put proxy.foo.com cert and key on proxy server

scp keys/proxy.foo.com.{crt,key} proxy:/etc/proxy-ssl/

9. Install squid proxy and stunnel on proxy server

On Debian/Ubuntu:

apt-get install squid3 stunnel

10. Configure & start stunnel

  1. set ENABLE=1 in /etc/defaults/stunnel.conf
  2. In /etc/stunnel/stunnel.conf

    accept  = 12346
    connect = 3128
  3. /etc/init.d/stunnel4 start

11. Create .pac file somewhere on an https url

function FindProxyForURL(url, host)
      return "HTTPS proxy.foo.com:12346";

Make sure that the certificate of the https server is one that the browser will accept.

12. Set proxy autoconf to the url to this .pac file

Spanner->Preferences->Under the Bonnet->Change proxy settings->Automatic Proxy Configuration

Set the URL to where the file is, including “https://”.

13. Try it now. It should fail with SSL errors

It should fail because proxy doesn’t accept your cert (you don’t have a cert in the browser yet). Don’t continue if you get some other error.

14. Create client cert signed by your own CA

./build-key my-proxy-key

Don’t set a password.

15. Convert the client key+cert to .p12, because that’s what Android and Chrome wants

openssl pkcs12 -export -in keys/my-proxy-key.crt -inkey keys/my-proxy-key.key -out my-proxy-key.p12

It’ll ask for a password that will only be used in the next step. No need to save it for later.

16. Import the client certificate into the browser

On your Chrome (or chromebook) go Spanner->Preferences->Under the Bonnet->Certificate Manager->Your Certificates->Import (or “Import and Bind to Device”).

17. Try to browse somewhere. Now it should work

Make sure you’re actually using the proxy. Go to www.whatismyip.com or something and make sure that it sees the IP of the proxy. It’ll probably tell you that you’re using a proxy. If it doesn’t work then good luck. :-)


Like I said it seems that it falls back to connecting directly, even though the .pac file doesn’t have a fallback mechanism configured. Stay tuned for the IPSec version.