This chapter explores self-directed creative and collaborative discovery as a mode of engaging the digital native in new and effective learning experiences. It considers student feedback from an initial experiment in self-directed creative and collaborative discovery using iPads as a mode of engaging music students in group electronic music-making practices. It examines the metalearning strategies adopted by the digital native and in doing so assesses the necessary re-adjustment of pedagogical assumptions required, and resources available, for successful results in this new and evolving context. D. G. Messerschmitt and C. Szyperski introduce the metaphor of an “ecosystem” to describe the complex web of relationships involved in current software. A determination to avoid merely reproducing existing skills or emulating conventional musical approaches enhanced learning and creativity. Participants encountered several impediments to learning through the iPad. The creative and collaborative learning that took place with the iPad Orkestra revealed several pathways.