Is there an easy way to enable SSL from within a standalone application or by using a config.ru file. I'm trying to build a simple Sinatra app that has the ability to reference its own certificates rather than passing them in from the command line.
Easy way, no. This is not supported. You'll need to hack into calling EM::Connection#start_tls yourself. See https://github.com/macournoyer/thin/blob/master/lib/thin/backends/base.rb#L136
@macournoyer in all seriousness: is this a feature or a bug?