What I am trying to do is debug an issue with my Ruby installation. There is a known "issue" where the CA cert file path is hardcoded to a location that doesn't exist anywhere except the build machine that the Ruby package was made on. This is detailed here:
https://groups.google.com/forum/#!topic/rubyinstaller/DVIDvs7xKC0
There are a number of "solutions" to this problem, most of which are captured here in this Stackoverflow Question:
http://stackoverflow.com/questions/11703679/opensslsslsslerror-on-heroku
I also found this gist: