This chapter examines how US post-conflict diplomacy toward Italy evolved from the final phase of World War II to the early Cold War. Initially shaped by the need for wartime stabilization, the American “good occupiers” gradually shifted from providing tentative support for antifascist moderates to adopting a proactive strategy of anticommunist containment. The chapter demonstrates how the Italian case fits the broader pattern of American post-conflict diplomacy, which involves transforming former adversaries into partners. However, it also highlights the essential role of Italian agency in this process. As the Truman administration came to view Italian stability as vital for Western security, Italian pro-Western moderates, in turn, used US aid and political support to secure reconstruction and international rehabilitation. Finally, the chapter highlights the contribution of official and unofficial diplomatic networks, including labor and cultural exchanges, to shaping US–Italian relations during this process.