One of the more puzzling aspects of Kant’s political thought is his insistence on the duty to obey even oppressive rulers combined with his belief in the republic as the only rightful constitutional form. In arguing that resisting oppressive power is as wrong as seizing it, Kant seems committed to the awkward position of denouncing as unrightful any attempts made by the people to establish the only rightful form of constitution. Several roads are available for anyone who might be inclined to attempt to dissolve this tension on Kant’s behalf. I will discuss the purpose of the civil condition and the obligation to move to it from the state of nature, arguing that the purpose of the state for Kant is to secure peace. I also contend that the social contract neither causes the state to exist nor justifies obedience to it. I will proceed to contemplate the civil condition as a state of freedom and, with that in mind, ask two questions about obligation, one relating to the republican form of the state and one to non-republican despotic forms. How can it be that all members of the republic are said to remain free while obligated to law when only a few are granted the law-making citizenship status which is supposed to dissolve the tension between freedom and obligation? How can it be that subjects are obligated to obey an oppressive regime that abuses its authority? These discussions will take us through the role of representation, the people as cause and the status of law, to the state as progressive.