This article aims to explore the evolution of school leadership in Italy toward a model of leadership for learning. Italy is undergoing radical changes in the governance structures (school autonomy and accountability) affecting schools in general, and school principals in particular, based on the way they promote, manage, and monitor the improvement of student learning. This has created an interesting, fertile ground for researchers to review how the policy-mandated initiatives are impacting on leadership for learning in schools. This article addresses two main questions. The first question explores how the new governance structures facilitate or impede an effective approach to leadership for learning. The second question explores whether the accountability reforms acknowledge and respect the history and traditions in which leadership is culturally embedded. This article concludes by presenting the implications for future policy initiatives based on the need to link school accountability and school improvement.