This paper offers a new interpretation of Kant's relationship with skepticism in the Groundwork for the Metaphysics of Morals. My position differs from commonly held views in the literature in two ways. On the one hand, I argue that Kant's relationship with skepticism is active and systematic (contrary to Hill, Wood, Rawls, Timmermann, and Allison). On the other hand, I argue that the kind of skepticism Kant is interested in does not speak to the philosophical tradition in any straightforward sense (contrary to Forster and Guyer). On my reading, Kant takes up a skeptical method in the Groundwork as a way of exposing certain obstacles in our ordinary and philosophical thinking about morality. The central obstacle he is interested in is practical in character, arising from a natural tendency we have to rationalize against the moral law. In attempting to resolve this tendency, I argue, the Groundwork turns out to have a profoundly educative task.