Ever worked on a web application and thought that it really could be improved? Adding a few fixes or tests to existing code helped in the short-term but could a redesign have been far more effective? And if you had wanted to do so, how could you have gone about it? This session will present an example of how an existing web application, using the Ruby on Rails framework, was redesigned. This was done for user interface as well as the application feature set. Building an extensive set of tests at various levels i.e. the interface, the application, and the database helped ensure that existing and new features worked seamlessly. The use of a light-weight deployment system made the entire process of deploying code easy and less error-prone.