I wanted to love JRuby (Ruby 1.9 emulation) but bugs like this: https://jira.codehaus.org/browse/JRUBY-5529 causes HTTPS calls to services like Stripe to fail. That bug has been open for over one year now.

Other bugs like this: https://jira.codehaus.org/browse/JRUBY-6181 cause Capistrano deployments to fail (but there is a workaround).

Lack of a clean implementation of something as fundamental SSL libraries and the inability of the main committers to address those shortcomings pushed me back to a traditional Ruby approach.