This study compares hope in street youth, former street youth, and school youth (aged 12-18) in Tanzania. Responding to Snyder's hope theory, the author argues that not only personal agency but also the stability of living context (street, shelter, home) shapes hopefulness. Employing qualitative and quantitative analyses, the author presents a framework that shows considerable differences by youth group in hope conceptualizations. Youth in unstable environments avoid hope to circumvent failure and instead attribute success to luck and other external factors, whereas youth in steadier environments rely on internal resources, seeing themselves as critical agents in engendering hopefulness. Taking youths' differing living contexts into account, the author proposes a contextual model of hope that consists of "hope instruments," "hope outcomes," and "pathways to hopefulness."