This article examines how the pre-migratory experiences of 90 Bhutanese, Burmese, and Iraqi refugee youth shape their aspirations, needs and capabilities as they transition to postsecondary education and work in the American urban context. It further explores how their schooling experiences in precarious urban school districts influence their trajectories. Drawing on two ethnographic projects spanning three years each, the authors rely on participant observation, semi-formal and formal interviews, focus groups, and documents for their analysis. The authors apply the notion of "cruel optimism" to explain the translation of refugee youths' aspirations post-arrival as they transition from war, refugee camps and illegal alienage to the grim landscape of public education in postindustrial cities like Philadelphia. Coping with residual trauma, interrupted schooling and the pressures of poverty, youth experience a "continuum of precarity" in their lives that begins in their flight contexts and extends into their post-resettlement social worlds. As public education becomes increasingly unstable, their narratives offer a lens to consider the moral contradictions of third country refugee resettlement. Future research should tease out the unique and multiple transitions refugee youth make across contexts and how their interactions with educative institutions belie the humanitarian promise of better lives.