In January 2018, I find myself racing frantically around Jigjiga with a local smuggler and a diaspora Somali known as a raucous opportunist. The two men work collaboratively to release a truck impounded at one of Ethiopia’s border checkpoints. Analyzing this situation, this chapter shows how the problems of moving goods across Ethiopia’s borders facilitate mutual interests and coordinated activities in the city. The situation ultimately scales up to involve a coalition of people from many of Jigjiga’s important social categories: diaspora (qurba-joogs) and locals (wadani), Somalis and non-Somalis, kin and nonkin, wealthy businesspeople and marginalized workers. Delving into situational analysis, this chapter introduces Jigjiga’s dynamic social fabric as it illustrates how people use urban space as a platform for managing cross-border connections and circulations. It focuses specifically on how border-related business collaborations converge in Jigjiga’s chat dens, where men create and evade social connections as they chew the mild narcotic stimulant known as chat or khat. Analyzing these locations and how they function as frontiers of relationship management, the chapter illustrates how elements of Somalis’ nonhegemonic or “egalitarian” cultural ethos converge to reinforce, rather than challenge, government hierarchies, border securitization, and urban inequalities.