After 2010, hundreds of diaspora Somalis left seemingly stable lives in cities of North America, Europe, and Australia and flocked to invest in Jigjiga, a post-conflict boomtown ruled by an unstable authoritarian administration. This chapter follows these diaspora businesspeople beyond Ethiopia’s borders and explores how their motivations for, and practices of, return-migration to Ethiopia are shaped by the experiences of migrant life in cities outside the Horn of Africa. Drawing on fieldwork among Somali businesspeople in South Africa and the US as well as Jigjiga, I show that Somali return-migrants to Jigjiga are driven by a complex mix of motivations, including responsibilities for family support, perceptions of business opportunity in the Horn of Africa, and experiences of precarity and risk in cities abroad. The implication is that social transformations in the Ethiopia–Somalia borderlands cannot be analyzed only at a local level. These ongoing shifts in securitization and urbanization in the Horn’s borderlands are entangled with “urban borderwork” in cities far beyond Ethiopia. This analysis not only situates Jigjiga in a broader world of cities and social relations; it also pushes us to think more deeply about the dynamic relationship between city-making and border-making in the world more broadly.