Previous definitions of peer-assisted learning portray the peer-teacher as a non-expert in teaching content and delivery. In this paper, we reflect on a near-peer initiative at our medical school which seems to depart from this definition. This initiative involves intercalating medical education students in the delivery of foundational sessions on professionalism for first year students for a full year, with individual supervision and support from an experienced teacher and extended medical education study. Reflections from a range of people involved are brought together to begin to understand the supportive features and challenges of near-peer teaching in our context and to identify areas for future research. These reflections highlight the potential for differences and contradictions in the ways that teachers and learners are understood within peer-assisted learning initiatives, and emphasize the need to consider the teaching context in peer-assisted learning scholarship.