Kant's commitment to autonomy raises difficult questions about the very possibility of Kantian moral education, since appeal to external pedagogical guidance threatens to be in contradiction with autonomous virtue. Furthermore, moral education seems to involve getting good at something through repetition; but Kant seems to eschew the notion of repeated natural activity as antithetical to autonomy. Things become even trickier once we remember that Kant also views autonomous human beings as radically evil: we are capable of choosing rationally and autonomously, but, left to our own devices, that same capacity for reason might tempt us to choose only out of a concern to satisfy our happiness. We thus need a moral education which realizes autonomy while dodging the dual bullets of external natural forces and internal evil forces. Ultimately, his concerns about external natural forces and internal evil forces do not lead Kant to reject either moral education or a role for repeated activity in it. Rather, he advocates a carefully circumscribed appeal to repeated activities within a course of Socratic moral education focused on encouraging the student, subjectively and first-personally, to claim her autonomy, resulting in the cheerful and vigilant exercise of virtue as an aptitude.