When I created my certs using openssl I made sure to have correct subject alternative names (i.e. an appropriate DNS name as a SAN in the cert) and I believe that a matching CN doesn't hurt here either. Whatever it mentions in the cert as SAN (i.e. a correct DNS name) must be ...
I would admit that windows is a really low priority for me. Gunicorn is done first to be deployed on POSIX/UNIX platforms. That’s a desirable goal anyway :) Thanks for taking the time to look at this. I really appreciate it. I know your time is very limited. ...