Pastoral care structures in New Zealand schools often include a role of dean. The dean’s responsibilities are often defined by schools to satisfy growing expectations of schools’ responsibilities for student wellbeing and achievement. This study explored the role of year-level deans within one state co-educational secondary school. Senior managers, deans, teachers, and students were interviewed, and deans completed a daily activity log. Findings indicate challenges exist for providing care for all students owing to the reactive nature of the role and unclear reporting lines. Results indicate that collaborative approaches to pastoral care may improve its provision.