Software Systems are designed to run on specific devices but eventually, a new one arises that may not be apt to run the system. Time ago, Web apps were intended mostly for desktop devices; then the arrival of the mobile devices required to revisit UI layouts, and later Smart devices allowed a more sophisticated user experience. During the development process, there was no clear definition of the technology adoption roadmap that affects the access from new devices like Smart TVs or Smart Watches. As long as time goes by, applications become legacy because of many reasons like lack of maintenance or the advancement of new incompatible devices. This study’s main contribution to these limitations is an empathetic approach to assist this migration of legacy apps to new devices based on Markov chains that are a predictive user behavior method. Available functionality is prioritized, the experience of User Interface is re-thought, and the new experience is designed. We report the experience of applying the approach to a legacy app with an experiment performed by fifteen participants. The outcome highlights that a dynamic user interface based on the Markov model provides improved usability metrics of the ISO for the users, evidenced in the productivity labor, Fitt’s and Hick’s laws, the efficiency, the effectiveness, and satisfaction through comparison between versions. This work suggests this model makes possible a smart and proactive interface design plus the age and interests responsive web contributing to the economy of context
