Can we automatically learn how users expect an application to behave? Yes, if we consider an application from the users perspective. Whenever presented with an unfamiliar app, the user not only regards the context presented by this particular application, but rather considers previous experiences from other applications. This research presents an approach to reflect this procedure by automatically learning user expectations from the semantic contexts over multiple applications. Once the user expectations are established, this knowledge can be used as an oracle, to test if an application follows the user’s expectations or entails surprising behavior by error or deliberately.