This paper examines the benefits and obstacles to young people’s open-ended and unrestricted access to technological environments. While children and youth are frequently seen as threatened or threatening in this realm, their playful engagements suggest that they are self-possessed social actors, able to negotiate most of its challenges effectively. Whether it is proprietary software, the business practices of some technology providers, or the separation of play, work, and learning in most classrooms, the spatial-temporality of young people’s access to and use of technology is often configured to restrict their freedom of choice and behavior. We focus on these issues through the lens of technological interactions known as “hacking,” wherein people playfully engage computer technologies for the intrinsic pleasure of seeing what they can do. We argue for an approach to technology that welcomes rather than constrains young people’s explorations, suggesting that it will not only help them to better understand and manage their technological environments, but also foster their critical capacities and creativity.