Large scale enterprise software systems are inherently complex and hard to maintain. To deal with this complexity, current mainstream software engineering practices aim at raising the level of abstraction to visual models described in OMG's UML modeling language. Current UML tools, however, produce static design diagrams for documentation which quickly become out-of-sync with the software, and thus obsolete. To address this issue, current model-driven software development approaches aim at software automation using generators that translate models into code. However, these solutions don't have a good answer for dealing with legacy source code and the evolution of existing enterprise software systems. This research investigates an alternative solution by making the process of modeling more interactive with a simulator and integrating simulation with the live software system. Such an approach supports model-driven development at a higher-level of abstraction with models without sacrificing the need to drop into a lower-level with code. Additionally, simulation also supports better evolution since the impact of a change to a particular area of existing software can be better understood using simulated "what-if" scenarios. This project proposes such a solution by developing a web-based UML simulator for modeling use cases and sequence diagrams and integrating the simulator with existing applications using aspect-oriented middleware technology. I would to thank my research advisor, Dr. Robert Chun, for encouraging me to follow my dreams and providing the support and coaching to help me get there. In 1990, I graduated from San Jose State from the Computer Science department with the knowledge I needed to carry my career in the industry for ten years. In 2000, I came back to SJSU, seeking a Masters to prepare for the next ten. Standing here now, six years since the start of that journey, and looking back; I am confident that this work will help me reach that goal. But, to my pleasant surprise, I ended up with more than I could have imagined. Dr. Chun, you have taught me how to make the best of my talents, how to focus my research and let creativity drive the work, and most importantly, how to make contributions back to into the field. This, I expect, will live with me beyond that ten year goal I had originally projected. It will live with me for the rest of my life. And for this, I am forever grateful. I would also like to thank Dr. Lee Chang and Dr. Suneuy Kim for reviewing my work and providing valuable feedback. In addition, I am grateful to Dr. Chang for the intense but worthwhile semester with UML, Patterns, and Refactoring in the CMPE 221 course-the result of which formed some of the motivation for my research. And last but not least, no person can make a journey such as this without strong family support. To my beautiful wife, Mai-Tram, for your sacrifices those last six years; and, to my wonderful two children, Audrey and Pascal, who have been wondering why their dad always stays up late at night… To you, I dedi...