I had a SSL certificate for a while, but actually using it throughout the site without showing users Big Scary Error Messages is not quite trivial. The activation energy for digging through several hours of edge cases was lacking... until today. ("Whoops, while you don't know you're doing it, you pull an unnecessary CSS file into the cached CSS for the registration page which references a background image on an absolute http:// URL. Your registration page now throws an error on IE. You lose." "You have approximately 150 images on the site linked as handcoded img tags rather than through Rails' image_tag helper, because when you were a Rails newbie you did not know that existed. You now get to rewrite all of them so that they can use SSL asset caching magic." etc, etc)