One of the questions that Heidegger presents in his paper, "Plato's Doctrine on Truth", is the distortion as he sees it of paideia--that is the loss of the essential elements in education. This loss is characterised according to Heidegger, by a misconception of Plato's concept of teaching and learning. By undertaking an historical examination, Heidegger provides a means to rectify this loss. With reference to past, present and future philosophical perspectives of teaching and learning as particular spaces, an attempt is made in this paper to examine Heidegger's reading of paideia within the context of online learning. This, for many contemporary writers on education, is an encounter with new literacies, new knowledge and the adoption of an online environment that challenges the hegemonic order of the institution as the purveyors of knowledge. Teachers within this new environment are, however still constituted as experts and their knowledge is seen as ultimately inviolate. Heidegger in his re-interpretation of Plato sees the teacher as leading the students to where they might make themselves intelligible within the space of their being. This alignment forms an acceptance and a challenge to the metaphysical concepts of uniformity of being and place that limits the potential of knowledge as something that is fixed and complete. The experience of the social web or Web 2.0 has seen a shift in learning premised upon dialogue, exchange and constantly shifting horizons. Within this context, the teacher is recast as a craftsman, creating learning opportunity within dialogic exchange. The heightened sense of involvement that is revealed in this context lays the ground for a future visioning of education where emergence is seen as essential, unlike a re-working of authorisation to learn that inhibits student and teacher alike in new attempts at revitalising education.