In juxtaposition with the myth and tragedy of Ovid’s Medea, this paper investigates the possibility within the Kantian conception of agency of understanding moral evil as acting against one’s better judgment. It defends the thesis that in Kant self-deception, i. e. the intentional untruthfulness to oneself, provides the fundamental structure for choosing against the moral law. I argue that, as Kant’s thought progresses, self-deception slowly proceeds to become the paradigmatic case of moral evil. This is discussed with regard to two important topics in his later moral philosophy: the doctrine of radical evil and the crucial role of the duty of truthfulness in ethics. The inquiry into Kant’s theory of conscience unfolds both against this theoretical background and in light of its historical roots in the polemic against casuistry and probabilism. This contribution closes with a brief look at the tools Kant implements to counter this tendency to self-deception in moral judgment and particularly at the role casuistry plays within his conception of moral education.