Increasing the perception of legal risk via publicized litigation and lobbying for copyright law enforcement has had limited success in reducing unlawful content sharing by the public. We consider the extent to which engaging in file sharing online is motivated by the perceived benefits of this activity as opposed to perceived legal risks. Moreover, we explore moderators of the relationship between perceived risk and perceived benefits; namely trust in industry and legal regulators, and perceived online anonymity. We examine these questions via a large two-part survey of consumers of music (n = 658) and eBooks (n = 737). We find that perceptions of benefit, but not of legal risk, predict stated file sharing behavior. An affect heuristic is employed: as perceived benefit increases, perceived risk falls. This relationship is increased under high regulator and industry trust (which actually increases perceived risk in this study) and low anonymity (which also increases perceived risk). We propose that, given the limited impact of perceived legal risk upon unlawful downloading, it would be better for the media industries to target enhancing the perceived benefit and availability of lawful alternatives.