This article explores the contextual factors that shape mentoring practice in Art Initial Teacher Education. Based on in-depth interviews, nonparticipant observations and stimulated recall interviews with participants, we examine how various factors related to the context of mentors' work influence their approaches to subject matter mentoring. Adopting a discursive stance to mentoring, we use critical discourse analysis to expose connections between mentors' language, ideas, and beliefs and the broader context of subject matter mentoring. In each mentoring setting studied, the analysis surfaces distinctive contextual factors that are grounded in mentors' interpretations of the roles and functions of their subject matter domains. We show how these factors inform mentors' perceptions of the purposes and processes of mentoring and their enactments in practice. Our findings offer an extended perspective to subject matter mentoring and new directions for thinking about context in mentoring. Implications for mentor preparation and selection are discussed.