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Research on principal preparation suggests that the internship is widely considered to be the most important component of principal preparation (e.g., Anderson & Reynolds, 2015), and high quality internships are, at least in part, defined by support from expert principal mentors (Clayton et al., 2013). The purpose of this study is to explore the principal mentor-intern relationship of 23 full-time, job-embedded interns. Specifically, we analyzed over 700 weekly reflections to trace the development and quality of interns’ relationship with their principal mentor. We found that principal mentors played a key role in determining the quality of interns’ experiences, particularly in terms of the work opportunities provided to the intern, as well as the levels of autonomy allowed and support received.