In this case study, the author investigated intersections of secondary students' musical engagement in a Songwriting and Technology Class (STC) and outside of school. The study traces the experiences of three individual participants and three participant groups (six embedded cases in total) in the creation, performance, recording, and production of original music over the course of a culminating class project. Findings suggest that the STC allowed students to experience smooth transitions between their musical engagement and learning in and out of school. Key factors that contributed to participants' engagement in the STC were (a) their experience with instruments and software outside of school and (b) use of popular music. Participants' engagement in the STC (a) informed and influenced the ways they listened to music outside of school, (b) broadened and deepened their aesthetic preferences, and (c) provided an environment in which participants could experience and negotiate their perspectives on issues related to popular music and the music industry. Participants also saw the STC as related and connected to their current and future lives as musicians. The study supports the inclusion of curricular offerings that allow for crossfading or overlap between students' in-school and outside-school musical experiences.