This chapter seeks to locate and elucidate the philosophical precedents and mechanisms in late-antique and Byzantine Christian thought that inform the tension between the rigorous affirmation of autonomous moral determination, on the one hand, and the self-effacing quality of ecclesiastical and monastic life, on the other. Though expressed with some variance and terminological inconsistency, the majority of Christian writers affirm some version of 'free will' and universally attribute the capacity for moral development to all humankind, developing and altering paradigms from the mélange of philosophical concepts present in Middle- and Neoplatonism. No less prominent, however, is the assertion—both tacitly and explicitly—that private moral judgment and individual conscience are unreliable. Each human being not only requires a pedagogical process for proper moral development but also depends upon the presence and guidance of a heteronomous 'other', whether human or divine. This chapter will accordingly seek to demonstrate that, while Christians of late antiquity and Byzantium considered free will and moral determination to be an inextricable aspect of moral psychology, they did not have the same understanding of autonomy that emerged so forcefully during the Enlightenment and in its wake.