This paper provides a conceptual synthesis of literature that addresses intersections of mental health, poverty, and school. It is based on a research synthesis for the youth policy framework for Ontario, Stepping Stones. The paper addresses research on challenges involving income inequality, poverty, and mental health that impinge upon school, and examines the enduring ill effects of these issues and academic struggles on young lives. It suggests practices that show promise to support youth. Findings suggest that transitions through school involve multiple developmental negotiations and are a critical site of slippages and successes. The paper ends with a set of reflective questions around age out (of the child and youth services system), the need to address stigma by animating the abundant character of young lives (addressing the subtleties and nuances of the life stories, biographies, and narratives of young people and their communities), the need for authentic collaborations across health and education, and working with and for young people as they collectively and individually determine and negotiate their lives.