This chapter seeks to present analysts with a path to transforming legacy systems into the new mobile-based paradigm of analysis and design. In order to best understand this journey, I must first clearly define what has been accomplished in the past; to do so provides today’s analyst with a better understanding of why applications perform the way they were designed and the reasons why they are not usable as we go forward with the new paradigm of advanced technologies in a mobile-based global economy. Reviewing these methods also allows analysts to continue supporting legacy applications and making enhancements to them until they are completely re-architected (which could take decades). Furthermore, because not all legacy analysis and design techniques should be eliminated, an understanding of past methods permits analysts to expand them to meet the needs of new digital-based technologies.