The purpose of this instrumental case study was to investigate the perceptions of preservice music teachers learning popular music and facilitating popular music learning experiences with elementary students in an after-school music program. Preservice music teachers enrolled in a popular music pedagogy course learned techniques for teaching and performing popular music, and facilitated an elective after-school 'ukulele program where they worked with students from two different elementary schools. Using interviews, researcher journals, preservice teacher reflections, and observations, we explored how preservice music teachers make sense of their experiences in learning to teach in a new musical context. We found that preservice teachers valued extended field experiences before student teaching, developed positive attitudes toward teaching popular music/musicianship, and required significant time to acquire the skills needed to teach in an informal learning environment.