An increasing amount of sensitive information is being communicated and stored online. Frequent reports of data breaches and sensitive data disclosures underscore the need for effective technologies that users and administrators can deploy to protect sensitive data. Privacy-enhancing technologies can control access to sensitive information to prevent or limit privacy violations. This chapter focuses on some of the technologies that prevent unauthorized access to sensitive information. These technologies include secure messaging, secure email, HTTPS, two-factor authentication, and anonymous communication. Usability is an essential component of a security evaluation because human error or unwarranted inconvenience can render the strongest security guarantees meaningless. Quantitative and qualitative studies from the usable security research community evaluate privacy-enhancing technologies from a socio-technical viewpoint and provide insights for future efforts to design and develop practical techniques to safeguard privacy. This chapter discusses the primary privacy-enhancing technologies that the usable security research community has analyzed and identifies issues, recommendations, and future research directions.