> Here's how others have done it without additional coding
>
> - http://www.google.com/search?q=squeak+apache+https
>
> I think that most sites are running their Squeak headless Web apps on the
> back-end of a front-end http server.

I think Jason wants to talk to a server via https/ssl from squeak, not
the other way around.

Maybe this helps:
http://www.stunnel.org/examples/https_client.html

Cheers
Philippe