One of the characteristics in software development is that software systems require changes once they are deployed in an operational environment. When the software is being used by the intended audience it is almost inevitable that errors are found, requirements change or new requirements emerge because of changes in the business processes. Depending on the nature of these modifications and the life-time of the software, the impact on the existing software will vary from simple error solving to complete architectural transformation. In this paper the architectural transformation is presented of stand-alone applications, redesigned into thin-client/server architecture to improve the application’s flexibility, interoperability, performance, distribution and scalability. The strategy proposed in this paper is a decomposition of the original application in which functionality is categorized and distributed in N-tier client/server architecture. The client application only contains the user-interface while the remaining functionality is split across multiple server applications. The software that is subject for redesign in this paper is a recently developed Point-Of-Sale application, initially designed as a stand-alone application. The goal of redesigning the application is to reduce the front-end hardware requirements, improve the application’s flexibility and make the application applicable for a wider range of usage. The redesign approach is evaluated by implementation of a proto-type Point-Of-Sale application, which has proven that an N-tier client/server Point-Of-Sale application is a feasible solution and leads to a very flexible and highly scalable application.