Collateral consequences (CCs) of criminal convictions such as disenfranchisement, occupational restrictions, exclusions from public housing, and loss of welfare benefits represent one of the salient yet hidden features of the contemporary American penal state. This chapter explores, from a comparative and historical perspective, the rise of the many indirect “regulatory” sanctions flowing from a conviction and discusses some of the unique challenges they pose for legal and policy reform. US jurisprudence and policies are contrasted with the more stringent approach adopted by European legal systems and the European Court of Human Rights (ECtHR) in safeguarding the often blurred line between criminal punishments and formally civil sanctions. The aim of this chapter is twofold: (1) to contribute to a better understanding of the overreliance of the US criminal justice systems on CCs as a device of social exclusion and control, and (2) to put forward constructive and viable reform proposals aimed at reinventing the role and operation of collateral restrictions flowing from criminal convictions.