Well, the error you're getting is a timeout error. It sounds like UPS doesn't even know you're trying to reach them. I would have thought that OpenSSL was all you needed, but maybe that's not the whole story. Double check your phpinfo() for "--with-openssl" at /admin/logs/status/php.

I feel like there's something missing. Unfortunately, I think it's got something to do with the server. I just don't know what it might be.