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This article examines the circumstances surrounding the escape from prosecution of SS-Obergruppenführer Karl Wolff, one of the central SS figures in the Mediterranean Theater during World War II. Key to his evasion of justice was his role in “Operation Sunrise”—negotiations conducted by high-ranking American, Swiss, and British officials in violation of the Western Allies’ agreements with the Soviet Union—for the surrender of German forces in Italy. After 1945, these officials, including most notably Allen W. Dulles, shielded Wolff from prosecution in order to prevent information about the negotiations from coming out. The details had to be kept secret, they believed, in order to avoid a confrontation with Stalin as the Cold War took shape. New evidence suggests that the Western Allies not only failed to ensure cooperation between their respective national war crimes prosecution organizations, but in certain cases even obstructed justice by withholding evidence.