Education is considered a key vehicle for creating hope among youth. This is important not only for hope's sake, but because increased hope is thought to reduce participation in various forms of violence. But while other goals for education in mitigating participation in violence involve special programming and step-by-step theories, hope is generally presumed to emerge spontaneously via education. We investigated the relationship between education and hope through qualitative cross-national research in Nairobi, Kenya, and Karachi, Pakistan. We argue that although education can be important for fostering hope, the pathways from education to hope are neither simple, linear, nor unproblematic and that there are features of education that contribute to hope and others that detract from it. We present a more nuanced understanding of the relationship between education and hope and delineate key features through which education may cultivate or dash hopes, with important implications for both scholarship and practice.