While “access models” represented by subscription services such as Spotify make vast libraries of music practically accessible to teachers, digital streaming programs also introduce new complexities to classroom settings. Therefore, the concept of digitalization in relation to listening requires the attention of researchers in education and didactics. This article examines the ways in which Swedish teachers use Spotify, including how usage influences teachers’ didactic choices and approaches to planning for music teaching and learning. Research participants included eight music educators with experiences in streaming music services in music classrooms. Findings show that digital literacy and the listening, teaching, and learning of music are inextricably intertwined; and that placing the application of music streaming in the context of a music classroom creates complications in practice. Implications highlight the importance of identifying and discussing complex issues occurring as a result of the use of streaming services in music classroom, gaining music streaming didactic literacy which is both a didactic competency that teachers use in planning for teaching, as well as a content for students to learn.