Just in case anyone else happens to stop by ...
WINHTTP_CALLBACK_STATUS_SECURE_FAILURE/WINHTTP_CALLBACK_STATUS_FLAG_SECURITY_CHANNEL_ERROR can be caused by attempting an https query to an http socket (e.g.
https://facebook.com:80). But, this occurs on both Windows 7 and 8, so it doesn't explain any Win8-specific trouble.
I'll post back if I ever find something more conclusive.
P.S. we miss you Dave