Within a few decades, the Italian people went from a partially colonized to colonizing power. A number of Italian patriots, therefore, who had espoused the ideals of self-determination, republicanism, and cosmopolitan nationalism, found themselves grappling with the rapid entry into colonization of the nation they had fought so hard to create. This article examines the thoughts and ideas of a select group of these individuals: Aurelio Saffi, Agostino Bertani, Alberto Mario, and Jessie White Mario. Focusing on their arguments in the 1880s and 1890s, it examines their reaction to the establishment of the French protectorate in Tunisia (1881), the British invasion of Egypt and defeat of Ahmad ʿUrabi's seemingly nationalist movement (1882), and the development of the Italian colony in East Africa. Throughout, the article emphasizes the shared importance of the civilizing mission in the ideology of both Italian cosmopolitan nationalism and colonialism. Though left-wing thinkers like Saffi or Bertani fervently argued for the freedom of nationalities and a brotherhood of peoples, their belief that a people needed to be sufficiently advanced for self-government, and that not all peoples were equally ready for that stage, allowed them to justify aspects of Italy's African empire. By examining their differing treatment of the people of Egypt, Tunisia, and East Africa, moreover, the article shows the extent and complexity of their classification of civilizations. While they showed a high level of sympathy for the more ‘Europeanized’ Egyptians, they viewed the people of Eritrea as ‘savages’ in need of Italian guidance and intervention. Finally, the article shows how they attempted to distinguish their version of benign and respectful colonization from the more avaricious or aggressive practices of the French or British empires.