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Following World War II, a group of American educators was assigned the task of evaluating the U.S. military government's program for reconstructing Germany's educational system. Although issuing a generally positive report, this education mission identified a number of persistent tensions that ultimately undermined America's efforts to rehabilitate and reform German schooling. As with the American occupation of Germany during the postwar era, current U.S. foreign policy directives include establishing educational institutions in the "broader Middle East" as a primary mechanism for inculcating democratic values and ideals. Determining America's success with these efforts, especially in ideologically conservative nations, poses a significant challenge to evaluators. Through an analysis of the 1946 Report of the United States Education Mission to Germany, this article presents a historical case study of the stumbling blocks, failings, and successes of one attempt to evaluate efforts in infusing democratic values into educational institutions in a fallen totalitarian state. © 2005 American Evaluation Association.