Teacher preparation for generalist (non-specialist) elementary teachers in Ontario typically comprises one compulsory music class. In entry surveys, many generalists describe themselves as highly apprehensive about and unconfident in their ability to teach music, confirming previous research. Using narrative inquiry, we explore the stories of both preservice and in-service generalist teachers. Data from focus groups with preservice teachers revealed that most participants felt markedly more comfortable with the prospect of teaching music in primary grades after taking our music courses; while fewer expressed confidence in teaching music to junior/intermediate grades. However, preservice teachers are rarely given the chance to observe or teach music while on practicum. Interviews with in-service generalist teachers revealed that a lack of confidence compelled them to take part in intentional, incremental, self-directed learning experiences to further develop their knowledge and skills for the elementary music classroom. The pandemic largely halted music activities, creating new barriers for generalist in-service teachers who teach music. The enduring gaps identified by this research are how to build more opportunities for generalist preservice teachers to practice their newly acquired skills while on practicum; and how to better support generalist in-service teachers to acquire additional skills for teaching music once in the classroom.