Prominent Kantian scholars, such as Korsgaard and Waldron, claim that the very existence of juridical-political institutions is sufficient to render laws authoritative. Critics argue that this view is unpersuasive as it requires subjects to obey grossly unjust laws. Here, I identify two problems facing scholars who reject the absolutist view of political authority proffered by Korsgaard and Waldron. First, when there is reasonable disagreement regarding a law’s legitimacy the Principle of Right generates contradictory obligations as it commands both disobedience and compliance. In clarifying this problem, I argue that individuals must disobey illegitimate laws where this requirement is co-extensive with the duty to leave the state of nature. However, disobedience amounts to domination when individuals are subjected to private judgments regarding the conditions of freedom. The Principle of Right cannot overcome this impasse as it does not offer reasons in favor of compliance that are distinct from those reasons legitimating the law. To address this issue, I supplement Kant’s account with Joseph Raz’s ‘service conception’ of authority to show that compliance can be rendered compatible with the Principle of Right. A second problem emerges when laws are blatantly illegitimate such that obedience cannot be justified. In these cases, the Principle of Right cannot guide legislative reform in an intuitively appealing way as it fails to address considerations of proportionality. Though this latter problem is not resolved here, identifying it helps to further clarify the relationship between Kant’s moral and political principles.