Since early development of information technologies, in particular computers and the Internet, there has been tension between those who believe these new technologies and their applications they have been mired in tension. Originally conceived and developed as tools for enabling high level, nonhierarchal engagement in problem-solving and development of information sources they have more recently been appropriated by those who believe the new technologies are best used for creating expert driven systems that guide users in obtaining important outcomes. One of the most eloquent social/educational theorists in recognizing this tension was Ivan Illich. Some of the most important early pioneers in computing technology were influenced by Illich's writings on tools conviviality, while many of the networking researchers were highly sympathetic to his ideas. In spite of this the idea of development of closed networks gained traction in popular culture, including in education. Many Internet-based education interventions, for instance, focus on creating directive systems that mimic traditional educational tools and goals in guiding students and/or teachers. One of the most important things education can do is teach students to reclaim conviviality of new information tools, especially applications focusing on engagement that have emerged in the last decade.