This article addresses a puzzle about moral learning concerning its social context and the potential for moral progress: Won't the social context of moral learning shape moral perceptions, beliefs, and motivation in ways that will inevitably "limit" moral cognition, motivation, and progress? It addresses the relationships between habituation and moral reasoning in Aristotelian moral education, and assesses Julia Annas's attempt to defend the possibility of moral progress within a virtue ethical framework. Focusing on the motivational core of the puzzle, the article argues that Self-determination Theory (SDT) provides resources for better understanding how moral progress is possible and how moral education can facilitate such progress.