How does users’ freedom of choice, or the lack thereof, affect interface preferences? The research reported in this article approaches this question from two theoretical perspectives. The first of these argues that an interface with a dominant market share benefits from the absence of competition because users acquire skills that are specific to that particular interface, which in turn reduces the probability that they will switch to a new competitor interface in the future. By contrast, the second perspective proposes that the advantage that a market leader has in being able to install a set of non-transferable skills in its user base is offset by a psychological force that causes humans to react against perceived constraints on their freedom of choice. We test a research model that incorporates the key predictions of these two theoretical perspectives in an experiment involving consequential interface choices. We find strong support for the second perspective, which builds upon the theory of psychological reactance.