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Supervision has been described as the "beating heart" and the "core" of clinical legal education. Yet lawyers who supervise law students in clinical programs have challenging and poorly understood roles within Canadian legal education. This article analyzes interviews with lawyers who supervise students in Canadian law-school affiliated legal clinics. Supervising lawyers describe the tensions between their roles as lawyers, supervisors and mentors, university and/or non-profit employees, social justice advocates, members of law societies, and clinic team members. These tensions often exist within an environment of lower pay, poor job security, substandard treatment by colleagues, inadequate training, and other aspects that paint a bleak picture. Despite these challenges, supervising lawyers describe intense satisfaction and inspiration derived from their work with students, clients, and the community. This article sheds light on the pedagogies employed by clinicians, their conditions of employment, and their roles in legal education more broadly. We conclude the article with our reflections about how law schools, clinics, and the legal profession can respond to the need to better support the vital work of supervision in clinical legal education.