The purpose of this investigation was to determine if a select group of adolescents exhibited behaviors and practices regarding digital music discovery, production, and sharing that influenced their classroom music instruction. The qualitative study focused on ways in which a group of adolescents informally engaged with digital music in relationship to learning music in their classroom. A constructivist–interpretivist viewpoint framed the theoretical perspective that a person’s knowledge constructions take place within the context of social interaction. In the early 21st century, young people interacting via digital social networking can experience and share music in ways previous generations could not imagine. Peer learning and exchange occur when adolescents share musical ideas and digital artifacts. In addition, autonomous learning takes place while interacting with a digital device. I used Mayer’s (2002) cognitive theory of multimedia learning to support an understanding of the learning effects associated with content-rich digital experiences. Linking social-constructivist and multimedia educational theories provided the conceptual framework needed to extrapolate meaning from adolescents’ preferences, influences, and feelings regarding digital musicking. In an instrumental case study, I followed four high school participants and their music teacher over the course of 6 months. The data consisted of participants’ detailed reflections and perspectives regarding digital music media discovery, production, and sharing. Detailed accounts collected from interviews and observations illustrated the behaviors of the participants, building a thick description. Although the research focused on adolescents, viewpoints of others emerged throughout the study, including those of peers, colleagues, and family members. Consequently, the investigation also considered what music teachers understood about their students’ out of school digital music discovery, production, and sharing. Findings show the convergence and divergence of digital music engagement in a high school music setting. Themes of experiencing music for personal identity, creativity, and popular culture intermix in classroom and informal learning environments. I present outcomes indicating direct implications for music curriculum development and suggest paths to connect in school and out of school music learning via digital music experiences. This study might help contemporary music teachers take advantage of students’ out of school digital music media practices to strengthen in school music programs.