I have setup an OpenVPN server and an HTTP proxy server on the same host in cloud. I have also configured OpenVPN client on my desktop. I have also setup redirection rules on the cloud host to redirect all port 80 and 443 traffic to the proxy server.
All the traffic from my desktop now passes through the proxy server. The proxy server witnesses all the traffic and handles it normally in the typical transparent proxy mode.
I have installed the fake root CA certificate on my browsers. The proxy server has SNI capability and handles the HTTPS traffic as it should, and also does all the inspection I need it do.
However some applications like Skype do not work via HTTPS inspection. But they can use an HTTP proxy server to make an initial CONNECT request. Based on the host detected in the CONNECT request, I can configure the proxy server to bypass HTTPS inspection. So when I manually configure proxy server IP address in Internet Explorer, I can get Skype to work. I am now trying to figure out how to automatically configure proxy server configuration in browsers, once the OpenVPN connection is established.
After a bit of googling I discovered some randomly available documentation on automatic proxy configuration using DHCP option 252, WPAD, etc. I also found that OpenVPN server side configuration provides "push dhcp" options. But can't find something concrete on that. Most of the content is for creating an OpenVPN connection through a proxy server. Obviously I don't need that. Wonder if any of you super hacks out here, could give me some good pointers. Could any of the super hacks here, kindly give me some pointers?
Thanks in advance.
P.s. Pardon the lengthy description, but I wanted to describe my purpose with maximum clarity.
