The proliferation of mobile devices has resulted in the creation of an unprecedented amount of context about their users. Furthermore, the era of the Internet of Things (IoT) has begun and it will bring with it even more context and the ability for users to effect their environment through digital means. Applications that exist in the IoT ecosystem must treat context as a first class citizen and use it to simplify what would otherwise be an unmanageable amount of information. This thesis proposes the use of context to build a new class of applications that are focused on enhancing normal human behaviour and moving complexity away from the user. We present Yakkit—a location based messaging application that allows users to communicate with others nearby. The use of context allows Yakkit to be used without the creation of a login or a profile and enhances the normal way one would interact in public. To make Yakkit work we explore different ways of modelling location context and application deployment through experimentation. We model location in an attempt to predict a user’s final destination based on their current position and the trajectories of past users. Finally, we experiment deploying the Yakkit service on different servers to observe the effect of distance on the message transit time of Yakkit messages. / Graduate / przemek@uvic.ca