Preparing teachers in clinically rich contexts requires teacher educators who are skilled and knowledgeable about university coursework as well as the complexities of classrooms. Retired teachers or principals have often assumed the role of field supervisor, bringing to their work extensive practitioner knowledge but often lacking theoretical knowledge of supervision. This qualitative case study examined the first-year experience of a reassigned teacher in the formal role of supervisor in a professional development school (PDS) context by analyzing the multiple perspectives of those affected by her supervisory practices. The purpose of this article is to discuss her interns' perspectives and the impact of her supervision on them. The findings show that this supervisor conflated the functions of supervision and evaluation, and as a result, her interns felt distress, disconnection, and disempowerment. The findings suggest that supervisors need a combination of practical and theoretical knowledge about supervision and that supervisors' professional learning warrants attention.