This chapter explores the relationship between freedom, regulation, and public policy. Adopting a “non-ideal” approach, it argues that there is no necessary connection between different conceptions of liberty and any particular sort of regulatory/public policy framework. Both negative and positive conceptions of freedom require a role for “regulation,” but whether this “regulation” arises from public policy or is best left to emerge through private agency in a competitive environment is a matter that can only be resolved by theoretical speculation and empirical inquiry. Many disputes about the freedom-enhancing capacities of regulatory regimes ought to be addressed within a framework that combines social scientific theory and evidence to understand the “compliance problems” arising under alternative institutional arrangements.