In 2017, we published in ACM Computing Surveys a review of the rapidly expanding field of research on behavioral hurdles and nudges in privacy and information security. In this chapter, we augment that review by considering novel research and interesting developments in this area. We consider the expanding literature on privacy behavioral and decision-making hurdles, the ongoing debate on rationality in consumer decision-making, and the so-called privacy paradox, as well as the expanding literature on both nudges and deceptive patterns (also known as “dark patterns”). We conclude by examining the effectiveness of nudges as tools for helping individuals manage their privacy online.