This article examines the entanglement between refugees’ Internet use and their present living conditions of resettlement in Sweden and Germany. It seeks to provide a new perspective by applying the operational concept of expectation as developed by Niklas Luhmann. Expectations emerge in the interplay between the user and the materiality as well as functionality of media technologies that are embedded in concrete living conditions. In the case of disappointed expectations, a cognitive or normative expectation stabilization strategy is applied. Based on in-depth interviews, it becomes obvious that where cognitive expectations are concerned, openness to change one’s expectations, and therefore learning, is increased.