This chapter examines challenges to medical data privacy and security in the age of artificial intelligence (AI). It analyzes how AI intensifies concerns about health record privacy and security and evaluates key elements of federal legal oversight, including the HIPAA Privacy and Security Rules, the Americans with Disabilities Act (ADA), and the Genetic Information Nondiscrimination Act. The chapter identifies significant gaps in the current regulatory system, such as HIPAA’s limited definition of covered entities, numerous exceptions allowing disclosure without consent, and lack of a private right of action. To address these shortcomings, the chapter proposes several reforms: expanding HIPAA’s definition of covered entities, revising the ADA to prohibit discrimination based on AI-derived health predictions, mandating disclosure of AI use in decision-making, and potentially adding a private right of action for HIPAA breaches. These changes would go far to align US law with advancing AI capabilities and enhance Americans’ medical data privacy.