Here I happen to have a Sony VAIO VGN-NW240F/T and a HDMI connected Samsung 2333. It's running Windows 10 so I could pull it up and see if I can summarize the setup to get 2 displays. If you have a failure well, there's system restore and if hardware, nothing will fix it.

There are folk that update drivers. Don't. Never update drivers just because. Have a good reason as drivers do not wear out.