This document summarizes a presentation given at RedDotRubyConf 2013 about continuously upgrading a legacy Rails application to newer versions of Ruby and Rails. It discusses the challenges faced such as compatibility issues, testing to prevent regressions, and deploying updates without downtime. Continuous integration, staging environments, monitoring and alerts were used to safely upgrade the application from Ruby 1.8.6 and Rails 2.0.2 to Ruby 2.0 and Rails 3.2 over time.