This case study examined the role of one high school literacy coach in a large high school in the Midwest. Over six weeks, interviews and observations were conducted and artifacts collected to develop an in-depth understanding of the evolving role of the secondary school literacy coach. The findings revealed the challenges within a complex setting including lack of clarity in definition and responsibilities, the importance of features that distinguish high school literacy coaching from elementary models, the role of the administrator, and the instructional role of the literacy coach.