The youth employment crisis in sub-Saharan Africa’s towns and cities is among the region’s top development priorities. High rates of youth under- and unemployment create significant obstacles to young people’s ability to become self-reliant, a crucial first step in the transition to adulthood. It is important to explore how local and global structures and processes create the hostile economic and social environment in which urban youth search for livelihoods. Only then can we identify the ways in which urban poverty brings insurmountable constraints on youth agency. We must understand the multitude of obstacles facing urban youth in their quest for decent work and secure livelihoods, how these differ by gender and educational status, and the implications of this for their longer-term social and economic development. This paper attempts such an exploration in the context of Arusha, Tanzania.