This chapter goes over the decision to purchase health insurance (or not). The way information is presented to individuals has a significant impact on their decision to purchase insurance to protect themselves from the financial consequences of health risks. Eliminating minor inconvenience costs or simplifying the insurance selection process can influence whether or not people purchase insurance. This chapter examines the roles of adverse selection and moral hazard in insurance-related behaviour, as well as the barriers to insurance uptake for individuals ranging from affordability to unobservable quality and information/choice overload. The chapter investigates the role of various nudges in increasing health insurance uptake.