Kant’s account of progress is often mistakenly portrayed as a steady movement toward realizing the highest political good. In this paper, I show that we also need to take non-linear progress into account. What exactly the highest political good is and whether it is realizable is a separate, complicated question, which I leave aside in this paper. Instead, I focus on whether and how political agents can be motivated by a belief in progress even in times when such a belief might seem unwarranted. My main concern is the following question: Is regression in terms of realizing our ideals a reason to abandon a belief in a Kantian account of political progress? As part of my answer to this question, I consider the relationship between Kant’s account of a guarantee of perpetual peace in the Treaty essay of the same name and his later reference to a historical sign in the Conflict of the Faculties. The paper considers how Kant’s account of progress allows us to confront apparent moments of regression within a substantive account of progress and a robust notion of what the realization of a political ideal would look like. I focus on how an individual in a Kantian account might be motivated by the idea of political progress and how his non-linear account of progress helps the agent to be further motivated to promote political change in situations of apparent regression.