Advancements in information technology often task users with complex and consequential privacy and security decisions. A growing body of research has investigated individuals’ choices in the presence of privacy and information security trade-offs, the decision making hurdles affecting those choices, and ways to mitigate those hurdles. This article provides a multi-disciplinary assessment of the literature pertaining to privacy and security decision making. It focuses on research on assisting individuals’ privacy and security choices with soft paternalistic interventions that nudge users towards more beneficial choices. The article discusses potential benefits of those interventions, highlights their shortcomings, and identifies key ethical, design, and research challenges.