Following community interaction theory and drawing upon the concept of boundary crossing, this paper investigates students' experiences of career learning across contexts when involved in placement activities. Specifically, this work focuses on students' experiences of continuity and discontinuity in relation to tensions naturally embedded in career education. For students to experience coherent career learning in lower secondary schools, career education must help relate career activities to career choice and learning by encouraging systematic reflections during preparation and follow-up. From a continuity/discontinuity perspective, when activities in out-of-school contexts are accompanied by an educational infrastructure, it can limit students' freedom to reflect on their experiences. Analysis results point to the emancipatory potential of collective reflection after the placement activities. Furthermore, the results highlight the unfulfilled potential of discontinuity as a source of career learning when moving across contexts.