The first commit for the DNSimple application was performed in April 2010, when Ruby on Rails was on version 2.3. Today DNSimple still runs Ruby on Rails, version 6.0. The journey from of the DNSimple application to today's version is a study in iterative development. In this talk I will walk through the evolution of the DNSimple application as it has progressed in step with the development of Ruby on Rails. I'll go over what's changed, what's stayed the same, what worked, and where we went wrong.