Pathways to Education is a community-based initiative for at-risk youth in downtown Toronto, Canada. Pathways aims to help youth in lowincome urban communities to complete and succeed in high school by providing various forms of academic, social, fi nancial, and advocacy support. This chapter describes-from the vantage point of one of its principal developers and fi rst program director-the Pathways to Education program, its development in one community in Toronto and then expansion to other sites in Canada, and its broader social context with respect to the value of promoting school completion among economically disadvantaged adolescents. The chapter summarizes data showing how the program has improved the educational attainments of its participants and concludes by suggesting how the research described in the other chapters of this book complemented the program’s primary activities by supporting and helping to understand the situations of certain groups of struggling learners.