This article offers a critical examination of the co-authors' experience developing and delivering a work-integrated learning (WIL) preparation course for communication and media studies undergraduate students in a large, research-intensive Canadian university. As a WIL pre-requisite, this praxis-oriented course was designed to proactively support WIL students' mental health and wellbeing. Uniquely, the course pairs a tenured faculty member with a WIL practitioner on staff within the faculty's advising office to provide a combination of foundational theory and practical implementation. The article presents four key components of the course that intentionally support students' wellbeing: 1) career exploration and portfolio development, 2) wellbeing literature and reflective practice, 3) guest facilitators with expertise in wellbeing, and 4) embodied agonistic pluralism. While acknowledging scalability and logistical challenges, recommendations from this case study offer insight for institutions interested in infusing a more intentional focus on student wellbeing into their WIL curriculum.