Context-oriented programs take into account detected contexts to alter an application so that it exhibits the most appropriate behaviour for that particular context. However Context-Oriented Programming (COP) focuses mostly on adapting behavioural aspects while mostly ignoring adaptation of the user interface aspect. In the HCI community, on the other hand, much research has been done on user interface adaptation but without paying much attention to the behavioural aspect. This PhD work seeks to reconcile both communities to allow programmers to build realistic applications that are more sensitive to their surrounding environment, as well as to evaluate the user acceptance of such systems.