On the Ethiopia–Somaliland border, harsh checkpoints imposed in 2015 relegated Somali kontarabaan (contraband) traders – mainly women – to precarious livelihoods. Beginning with an ethnographic description of crossing through these checkpoints, this chapter outlines a contradictory dynamic: Jigjiga, Ethiopia’s premier smuggling hub, has become the capital of a local government bent on hyper-securitizing its borders. Intensifying border security interventions and a wave of return-migration among the global Somali diaspora have made many local merchants viscerally aware of their marginality and immobility in contrast to people with foreign passports and government connections. For small-scale traders, Ethiopia’s borders tend to operate as dividers. For government-connected elites and diaspora returnees, the same borders often enable opportunities for business connections and mutually profitable alliances. This chapter uses this observation to critique what it calls the “connective cities, divisive borders” portrait of globalization. It explains the importance of thinking about borders and cities as interconnected spaces of daily life. It introduces the book’s main arguments: that African urbanites are active agents who work to refashion geopolitical borders and create opportunities from them, and that everyday practices of exchange and mobility in the city do not just produce urban space but also resonate more broadly into border management.