This paper examines a high school apprenticeship program with a focus on the opportunities for "expansive" learning within three different contexts: schools, the training centre and worksites. The authors assume that while young people differ in the degree to which they engage in learning within different sites, the institutional arrangements and features of different learning environments significantly influence their experiences and the quality of their apprenticeships. The authors' analysis of interviews with students and instructors involved in a carpentry program suggests that these sites exhibit several features associated with expansive approaches to workforce development. However, restrictions on learning occurred in schools partly because of the academic/vocational divide in curriculum. In the learning centre, the failure to address tensions rooted in power relations in the workplace limited students' learning. Similarly, students were confronted with the need to make trade-offs in the workplace that restricted their learning. The authors argue that taking steps to address these issues would enhance workplace practices and learning environments for apprentices. (Contains 4 notes.)