The case positions the reader as a faculty member who must advise a student who is struggling in his administrative internship. The case walks the reader through a set of internship experiences that place the intern in an increasingly uncomfortable position with his internship sponsor. These experiences encourage the reader to reflect on the responsibilities of the intern and the conflict that emerges when these responsibilities are not clear. The case is suitable for use in K-12 educational leadership programs, as well as in professional development for internship supervisors, for principals hosting administrative interns, or for faculty contemplating effective internship experiences for novice administrators.