This article examines the nature and significance of the activities carried out in France and Italy by the Congress for Cultural Freedom (CCF), an international organization that was secretly funded by the U.S. Central Intelligence Agency to support anti-Communist intellectuals, including those on the left end of the political spectrum. These two West European countries, with their large and politically influential Communist parties, were central to the CCF's work in Europe. The organization's task was complicated by domestic concerns and traditions that forced local intellectuals to stress their autonomy from the CCF International Secretariat and its U.S. patrons. The article uses the cultural Cold War and the competing interpretations of anti-Communism and cultural freedom within the CCF as a lens to explore the limits of U.S. influence and persuasion among the intellectual classes of Europe. By repeatedly asserting their independence and agency, the French and Italian members of the CCF helped redefine the character and limits of U.S. cultural diplomacy.