The significance of the regulative function of the reflecting power of judgment for Kant’s philosophy of history is widely accepted in the relevant literature. However, less attention has been paid to particular modes of reflection with reference to history. In the last paragraphs of the Critique of the Power of Judgment we find a distinction between the “theoretically reflecting power of judgment” and the reflecting power of judgment “in accordance with concepts of practical reason”. In the present paper, I attempt to stress the importance of this distinction for Kant’s philosophy of history. More specifically, it is my view that this distinction leads Kant to a double perspective on history, by means of which one can explain why the notions of Nature and Providence cannot be used interchangeably. Interestingly, at the same time, it facilitates a new understanding of what Kant in Religion within the Boundaries of mere Reason calls “revolution in the disposition of the human being”. Another notion which is crucial for the main argument put forward in the present paper is that of the “culture of discipline”. Although Kant introduces it in the third Critique, I attempt to show that this is the notion that mediates Kant’s two views on history.