This chapter explores Dante’s treatment of human freedom and moral responsibility as the constructive counterpart to the failures of heresy and despair. The discussion highlights how the poem not only theorizes freedom but dramatizes it through interpretive dilemmas that readers, like the pilgrim, must navigate. It begins with Marco Lombardo’s and Virgil’s discourses on free will in Purgatorio 16–18, which frame freedom in Aristotelian psychological terms. It then turns to Paradiso 3–7, where Beatrice’s discourses broaden the discussion into questions of determinism, vows, and atonement, dramatizing the difficulty of reconciling philosophical reasoning with theological claims. By showing how Beatrice’s account supplements Virgil’s framework, the chapter argues that free will, in Dante’s vision, is not an innate faculty of affirmation and denial but an active exercise of interpretive responsibility. Freedom emerges as the positive alternative to interpretive blindness, preparing the way for the final destabilizing vision of Chap. 6 .