If Neil Postman, were alive today, what would he say to Prensky, the originator of the term, "digital native", about the ways in which teachers should approach the wonders and perils of e-learning in their classrooms? As the Dean of a faculty of education which is devoted to both creating and critiquing a variety of digital teaching and learning strategies in K-12 and adult education contexts, I have kept a close eye on the developing metanarrative of the twenty-first century skills movement. Arguments and anecdotes from the movement's proponents concerning teachers' technological accountability and competencies are attractive and compelling to some educators at the same time as they are oppressive and disturbing to others. In order to deconstruct the technophilic discourses of Prensky, Trilling, and Fadel, I juxtapose their work with Postman's cautionary tales about totalitarian technocracy in schools. Postman wants educators to question their taken-for-granted assumptions about the ways in which they and their students should interact with technology. Prensky and his followers wish to provide educators with effective ways to involve their students in experiential learning partnerships through the use of serious gaming, e-books, crowdsourcing, and Facebook. As the views of Prensky and Postman are contrasted, a number of interesting issues emerge. What, for instance, is the nature of moral development and cultural identity formation when collective intelligence, hypertexts, and virtual relationships displace traditional textbook and face-to-face modes of learning? In this article, therefore, I attempt to synthesize the opposing perspectives of Prensky and Postman in order to establish a balanced and yet critical theory of the nature of e-learning.