Abstract This chapter explores contemporary regulation of medical privacy in the United States and Europe and its challenges. The need for privacy is a fundamental human necessity. Privacy relates to human beings’ ability to maintain their dignity and avoid disclosure of information that might be deemed unpleasant. It is also associated with personal autonomy and informational self-determination. At the same time, however, some degree of data sharing is essential to the appropriate treatment of patients as well as to the proper functioning of society in general and the healthcare system in particular. Thus, privacy cannot be limitless. Hence, this chapter discusses regulatory strengths and shortcomings and highlights gaps in the law. It also suggests further safeguards that policy-makers should implement in order to protect patients and data subjects.