Applied learning has become a feature of many innovative partnerships aiming to increase young people's participation in education and training so that they may complete Year 12 or its equivalent. Such partnerships frequently involve applied learning experiences that require students to transcend the boundaries of schools, workplaces and community organisations. Yet very little is understood about school-age students' first-hand experiences of learning through boundary-crossing activity and what role this plays in the students' development of new knowledge, skills and attitudes towards their education. This paper draws on a case study approach to present the experiences of young people who have participated in boundary-crossing as a feature of their senior applied learning certificate. It identifies themes emerging from the students' experiences of boundary crossing and draws on an Activity Theory perspective to conceptualise what can be learned from the contradictions and discontinuities arising from their experiences.