For Kant, the ideal of enlightenment is most fundamentally expressed as a self-developed soundness of judgment. But what does this mean when the judgment at issue is practical, i.e., concerns the good to be brought about through action? I argue that the moral context places special demands on the ideal of enlightenment. This is revealed through an interpretation of Kant’s prescription for moral pedagogy in the Critique of Practical Reason. The goal of the pedagogy is to cultivate the moral disposition, and the method consists of training in judgment. Unfortunately, Kant seems to wind up somewhere short of this goal, leaving the young person with only an idle wish for a properly cultivated moral disposition. In this paper, I argue that when we address the special issues that arise when the enlightenment ideal is brought to bear on practical judgment — issues that stem from the intrinsic connection between practical judgment and agency — we will see that there is no lacuna in Kant’s account.