This chapter highlights the continued struggles faced by Canadian youth in their transition from school to work. In July 2016 the unemployment rate for youth (aged 15–24) in Canada stood at 13.3% compared to the general unemployment rate of 6.9%. Many young people under the age of 30 who are employed are working in increasingly precarious conditions (e.g., temporary, contract, part-time, or low paid) or nonpermanent jobs. In this chapter, the authors focus particularly upon recent secondary school-based policy developments in Canada aimed at enhancing the transition from school to work for youth. They specifically focus our analysis on the country’s most populous province, Ontario, and demonstrate how the policy context in Ontario has prompted several initiatives and programs to support youth in transition from school to meaningful work.