The United States occupations of Cuba and Puerto Rico following the War of 1898 instituted immediate reforms to the educational systems of the islands. The imposition of public school systems modeled on those of the United States and a concurrent wave of Protestant schools established by American missionaries are well-known features of the imperialist project. Yet American reforms were shaped by what was known in the nineteenth century as “the school question,” or the controversy over the appropriate relationship between schooling, religion, and the government that had pitted the Protestant majority against Catholics and resulted in a consensus that religious-affiliated education should be permitted but relegated to the private sphere. The implementation of this consensus as the basis of occupation policy in Cuba and Puerto Rico, majority Catholic societies, contributed to the significant growth of a system of private Catholic schools and sparked debate about the relationship between religion, education, and nationalism. In an imperial context, “the school question” led to political polarization in the face of persistent US hegemony.