Increased interest in music technology education in recent years has prompted music teachers, technology educators and theorists to reconsider both the human and technical processes rendered by creative work in digital sound media. Music technology learning environments range from more structured classroom learning to informal, autodidactic practices, where student identity and creative agency are paramount. However, there is a need to develop more specific teaching and learning strategies that move beyond basic instructional or blended learning environments for digitally literate students (Darlis & Sari, 2021). This chapter discusses common learning practices of Digital Audio Workstation (DAW) users, and the dangers of superimposing conventional music teaching strategies to music technology when the learning style, participatory culture and multimodal affordances are inherently different. This article draws on a recent study involving a constructivist approach with secondary school students in Aoteaora New Zealand via creatively navigating "blocks" in students' autodidactic processes. Some findings are reported before some initial ideas of how teachers can incorporate aspects of individual identity (e.g., cultural, social, and political contexts) into DAW learning are offered. [This article was written with David Lines.]