This book examines the debate on the free will between the end of the Middle Ages and the first decades of the sixteenth century. The volume takes an interdisciplinary approach. Scholars with different backgrounds analyze a significant group of case studies: from the medieval vernacular lyric poetry (Sara Ferrilli) to Francesco Petrarca (Lorenzo Geri); from Lorenzo Valla's thought (Mariangela Regoliosi) to Giannozzo Manetti (Stefano Baldassarri); from Erasmus of Rotterdam (Pasquale Terracciano, Christian Houth Vrangbæk) to Martin Luther (Anders-Christian Jacobsen). The chapters delve into the plurisecular history of this crucial issue of western culture by focusing attention on the transition from the birth of Humanism to the dawn of the Reformation. Following the unfolding of the debate on free will allows to explore from a pivotal perspective both well-known books, such as Erasmus' Free Will, and lesser-known, but equally noteworthy, texts.