But measured against almost every marker of school performance U.S. officials used at the time – schools constructed, attendance rates, English acquisition, numbers of credentialed teachers – the United States’ efforts to establish systems of schooling for its new possessions were, at best, only marginally successful. Most historians have explained the failure of U.S. colonial schooling by highlighting the resistance of the targeted populations. And while these responses were certainly vital to determining outcomes, my paper examines a more fundamental problem: the structure of the state itself. The very partnerships that enabled the federal government’s expansion of schooling rendered the government dependent upon networks of allies and weakened the development of a centralized colonial apparatus. Moreover, the inherent localism of American public education was fundamentally at odds with the kind of centralized power required of colonial rule and impeded educators’ efforts to transplant U.S. school systems onto newly “American” soil. Indeed, my paper argues that colonialism exposed the cracks in the infrastructure of American schooling and the weakness of the federal government as an agent of its own empire.