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This paper examines the paradox of mentorship in secondary music education where long-term teacher-student relationships can become sites of ethical ambiguity, emotional overreach, and, in rare but critical cases, misconduct. Conceptually drawing on research exploring music teacher isolation (Sindberg, 2011), mentoring frameworks (Draves & Koops, 2011), and educator stress (Stringham & Snell II, 2019), this paper argues that the structural conditions of music education create a uniquely underexplored double-bind: they encourage deep bonds with students and simultaneously isolate teachers from professional community and support. The paper calls for preservice education programs and school districts to address these risks by emphasizing ethical preparation, psychological grounding, and systemic support networks.