Enhancing school-to-work transitions for youth is a policy focus of secondary schools in most OECD countries. This paper examines one organisation's efforts to encourage high school youth to consider careers in health care by providing them with summer internship opportunities. We adopt an embedded context approach to examine the effects on outcomes of trends in health care work, the institutional realities of schools and health services workplaces, and the behaviours of students, employers and educators engaged in the internship programme. Our analysis of interviews with youth and other partners suggests that different features of the programme within the broader context of changes in the health care workforce make it unlikely that it will fulfil its goal of addressing education-jobs mismatch. Part of the problem is that Canadian transition systems are characterised by a market approach that relies on employers to engage in long-term workforce planning and develop the capacities of a wide range of youth. Instead, we argue that more coordination and communication among partners is needed to ensure that a variety of youth are afforded opportunities to learn about as well as for work. (Contains 1 figure and 2 notes.)