This article analyzes the development legacies of Italian colonialism in Africa. The comparative-historical analysis shows that colonial Italy pursued “settler colonialism” in areas conducive to colonial settlement and large-scale exploitation, and “plantation colonialism” in areas with fewer resource endowments and settlement opportunities. In the immediate aftermath, while settler colonialism had a positive influence and plantation colonialism exerted a negative impact on economic prosperity, both types of Italian colonialism had strong negative effects on human development. In the post-1960 period, whereas the colonial legacy of plantation colonialism led to persistent poverty in Somalia, long-run development in Eritrea and Libya was contingent on critical junctures, which variously reinforced, destabilized, and/or transformed the institutional and developmental legacies of settler colonialism. I draw on the comparative-historical tradition emphasizing national orientation of European colonizers and natural conditions in colonized areas as key determinants of European colonialism and long-run development. However, I emphasize “factor endowments” as one such condition that defined Italian colonization strategies and institutions, finding little empirical support for factor endowments per se or precolonial ethnic centralization as principal determinants.