This article presents excerpts from a case study describing Angelica Dawson, a New York State music educator. Angelica makes improvisation a central part of her curricula in ways that transcend traditional offerings prevalent in American public schools. Qualitative research methods were used to document Angelica's work over the course of an academic year at a rural public school in New York State. Data collection utilized ethnographic techniques including interviews, observations and informal conversations. Data analysis employed interpretive coding guided by a constant comparative approach. Analysis revealed challenges posed by teaching improvisation in the school music context, including: conflicts with tradition; conflicts with the expectations of colleagues, parents, students, and administrators, and standing apart from the prevailing practices of colleagues. Angelica's story suggests that teachers who break from traditional pedagogical practices face profound challenges and feelings of isolation.