The factors which lead people to adopt or reject technologies of varying degrees of legality have not been studied extensively in information systems research. To address this gap, we combine literature in information systems and political ideology and theorize on the general influence of the personality traits openness to experience and conscientiousness on online media piracy. Furthermore, we propose differential consequences of the personality characteristic ambiguity intolerance for two different kinds of online media piracy, namely pirated online streaming and file sharing. We use clickstream data from 3,873 individuals in the U.S. to study their use of online media piracy websites. Contrary to what prior studies would suggest, we do not find that individuals with a more conservative ideology, and thus likely lower levels of openness to experience and higher levels of conscientiousness, engage in less online media piracy across the board. Instead, we find that individuals with a more conservative ideology, and hence likely lower ambiguity intolerance, exhibit lower use of a legally ambiguous technology (pirated streaming websites) whereas there is no difference in the use of a similar but legally unambiguous technology (pirated file sharing websites). We discuss how our findings impact the study of new technology adoption.