This chapter considers play as leading to unexpected innovation in advanced wireless technologies. It concludes that much of the potential for new media to enhance innovation actually echoes much older patterns, as evidenced by comparisons to wireless history. These are patterns of privilege, particularly class and gender privilege, reinforced by strict intellectual property protections. Detailed case studies are presented of the “wardrivers,” young male computer enthusiasts who helped map wi-fi signals over the past decade, and of earlier analog wireless enthusiasts. The chapter offers a solid critique of many present-day celebrations of technology-driven innovation and of the rhetoric of participatory culture.