I've got an application which is supposed to log in to a website to control some equipment, it does this over an https connection. The app compiles and runs on X11, OSX and win32 but for some reason it fails to connect over https on Windows. If you force it to plain http then it works so it looks like an OpenSSL dll problem. The issue I have is that while the testing system allows both http and https traffic, the final system is https only.

Does anyone know wether I could use a proxy like squid to take an http request and run it over https? It doesn't necessarily have to be transparent. I can change the URL's and request data in the client to suit.