The purpose of this instrumental case study was to examine what LGBTQ (i.e., lesbian, gay, bisexual, transgender, queer, or questioning) student teachers in music classrooms might learn from LGBTQ music teachers who served as external mentors outside the classroom setting. During the student teaching semester, 3 LGBTQ student teachers were each paired with a music teacher whose LGBTQ identity matched their own and who taught near the geographical region where student teachers hoped to secure employment. Each week, student teachers communicated with mentors via journaling, phone conversations, or videoconferencing. Additional sources of data were collected through individual interviews, focus groups, and Facebook postings. Across all cases, student teachers grappled with issues of LGBTQ presentation, providing student support and environmental contexts. Older teachers in socially conservative climates advised a cautious approach toward LGBTQ identity in the classroom, whereas the youngest mentor advised normalizing LGBTQ topics through full disclosure. Findings are discussed regarding the varied sociopolitical contexts LGBTQ music educators may encounter.