Many enterprise architects (EAs) have been rationalizing application and technology portfolios for some time, and the experience shows. It is a stable, relatively successful initiative that engages EAs in discussions with executives to champion the process. However, once beyond initial stages, rationalization can become more difficult as you encounter complexity and application and technology usage entrenchment. To address this, EAs must sharpen the specificity of their justifications in order to win over stakeholders with multiple demands on constrained funding.