This paper reviews the issues faced by developers using current technologies to implement web applications and examines these issues in the context of more modern tools such as Web Services and Rich Internet Applications. The paper explores the case of a particular company, briefly discussing its history, evolution and some of the requirements that have made a web based solution superior to available alternatives, ultimately leading to the development of a three tier helpdesk web application. The application’s development, functionalities and longevity are then reviewed and critically analysed with the aim of identifying flaws with its underlying architecture and the technologies employed to develop the system and other similar web based solutions.