This paper explores the challenges of partnership through an examination of a high school apprenticeship program in carpentry in Ontario, Canada. Focusing on the relationships between schools, trainers, employers and government, challenges relate to the ability to coordinate the program across institutions, achieve agreement on goals, gain commitment from employers and promote a culture of learning in the workplace. These areas need to be addressed more systematically by policy’makers and partners if such programs are to foster the learning and development of young people.