Most Canadian provinces offer high-school apprenticeships to facilitate students' transitions to skilled work and address employers' concerns about labour shortages. Using interview data with graduates from high-school apprenticeships in Alberta and Ontario, we analyse the impact participation in these programmes has had on their educational and occupational pathways. Findings show the importance of opportunity structures on the employment and education trajectories of young apprentices. High demands for skilled workers in Alberta, associated with the province's exploration of large oil sands deposits, are contrasted with a contracting labour market in Ontario, which is more dependent on employment in the service and manufacturing sectors. Findings show that economic conditions and the availability of post-secondary alternatives affect young people's decisions to enter and persist in apprenticeships. We also argue, however, that tighter regulatory frameworks are required to protect young people in apprenticeships from exploitative practices.