Every era of technology has, to some extent, formed education in its own image. That is not to argue for the technological determinism of education, but rather that there is a mutually productive convergence between main technological influences on a culture and the contemporary educational theories and practices. Thus, in the era of mass print literacy, the textbook was the medium of instruction, and a prime goal of the education system was effective transmission of the canons of scholarship. During the computer era of the past fifty years, education has been re-conceptualised around the construction of knowledge through information processing, modelling and interaction. Now, as we enter a new world of global digital communication, it is no surprise that there is a growing interest in the relations between mobile technology and learning. What we lack, however, is an innovative and enhancing educational framework for the mobile age. A framework for learning in the mobile age should recognise the essential role of communication in the process of coming to understand the world and in negotiating agreements among differing perspectives. It should also indicate the importance of context in establishing meaning, and the transformative effect of digital networks in supporting virtual communities that transcend barriers of age and culture. One starting point is to examine learning as communication. According to Dewey, then, communication is the central process of education. It is means by which we negotiate differences, understand each other’s experiences, and establish shared meaning. The conception of education as the liberal sharing of experience raises both philosophical and practical issues, which are re-surfacing in the age of mobile communication. A teacher has no ontologically privileged position, but is simply another participant in the conversation of learning. This does not fit easily with traditional classroom schooling. It challenges the classroom as an environment in which both the structure and content of discourse are regulated externally by the curriculum and the examinations system, and where communications are mediated by the teacher. The carefully bounded discourse of formal education contrasts with the rich interactions that children engage in out of school, through mobile calls, texting and computer messaging, and by conversing in online communities. These two worlds are now starting to conflict as children bring mobile phones into the classroom or share homework online. Rather than seeing mobile communication and online communities as a threat to formal education, we need to explore how education could be transformed for the mobile age, through a dialogue between two worlds of education: one in which knowledge is given authority through the curriculum, the other in which it emerges through negotiation and a process of coming to mutual agreement. Ironically, a process of learning by negotiation does occur in the world of formal learning, among those experts who set the curriculum, but learners (and most teachers) are generally excluded from that process. The description given here of learning as conversation in context is primarily based on the work of Gordon Pask (Pask, 1976). It derives from cybernetics, the study of communication and control in natural and artificial systems, and its more recent extension to second order cybernetics, the study of the mechanisms by which a system can understand itself. With a prescience that foreshadows recent developments such as the Semantic Web (the development of the worldwide web into a knowledge-based medium) and grid computing (pervasive computing power available like electricity on an international grid) Pask proposed a new conception of communication. Rather than seeing communication as the exchange of messages through an inert and transparent medium, he reconceived it as consisting of program sharing and linguistic interaction within a pervasive computational medium (Pask, 1975). Thus, media are active computing systems within which mind-endowed individuals (people and intelligent systems) converse.