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Existing research on compliance failures by individuals and businesses focuses primarily on information and incentive problems. This article develops a comprehensive framework for analyzing barriers to compliance, giving particular attention to resource and autonomy barriers, heterogeneity of the target population, multiple barriers to compliance, and problems that arise when a complex and ongoing set of actions is require to be “in compliance.” How governments react to compliance failures is heavily influenced by the social construction and political power of target populations. The propositions developed in the article are tested against the cases of the Swedish individual account pension system and welfare reform in the United States.