Completion rates are one measure of the success of apprenticeship training. But little is known about outcomes for youth who begin an apprenticeship in high school. This paper draws primarily on interviews with youth who did not continue training or work in their high school apprenticeship trade in two Canadian provinces. Our analysis focuses on why these youth decided to enrol in high school apprenticeship, why they did not continue and what they did afterwards. Findings suggest that a narrow focus on apprenticeship training completion diverts attention from the complex learning and work transitions experienced by most youth. Instead of assuming a linear pathway from school-to-trades work, we argue that partners involved in high school apprenticeship and policy-makers could do more to raise student awareness of multiple trajectories and skills transfer, make apprenticeship training more expansive, and increase the flexibility of pathways by providing greater articulation between different post-secondary education pathways and opportunities to change direction.