The idea that “humans are the ones making the music” (Pignato, this volume) is the starting point for reflection upon the factors beyond new technologies that encourage musical innovation. In their core perspectives, Pignato, Peppler, and Kigozi offer illustrations of practices that demonstrate the inseparability of context, informality, and innovation. Context is critical, as different settings afford access to different technologies and produce diverse sociocultural structures. Informality—as a learning style, an approach to engagement, and settings beyond the formal music education institutions—is important for its accommodation of playfulness, open-ended exploration, and improvisation around imposed constraints. I argue that these factors, and the innovative responses that emerge when technologies and creative people converge, are interrelated and multidirectional. Regardless of how advanced our technological capabilities become, innovation and new musical expressions remain products of humans interacting and exploring technological possibilities within a specific time, space, and social environment.