Proxy config question

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.

Is your clock set correctly on the windows box?

Does it work with the Windows Firewall disabled?

It's technically feasible, yes. I don't know that you can do it with squid (you might), but the SSL encapsulates plain-jane HTTP and the encryption layer is handled completely separately, so you should be able to create some sort of trivial proxy with stunnel or similar and a two-way pipe.

RTC is locked to our on site GPS so I don't think it's that. I also disabled the corporate firewall (which disables the Windows one on installation) but that makes no difference. I've found one machine that it works on but sadly that's my dev machine which has all sorts of crap on it, too much to go through one by one to figure out what it is.

Another option would be to rewrite the app and make client/server and just run the server element on one of my linux boxes. This is actually likely to be quicker.