The nature of learning is being augmented by new digital tools, particularly by mobile devices and the networks and structures to which they connect people. In this paper I examine: (i) the powerful perspectives on learning and development put forward by Vygotsky, (ii) an evolutionary educational design research approach, and (iii) notions surrounding the temporal nature of learning. Specifically, this paper presentation will focus on exploring my research from the present, in order to propose some preliminary thoughts on the nature of what I am calling Augmented Contexts for Development (Cook, 2010a; Cook 2010b); an extension of Vygotsky’s Zone of Proximal Development (Vygotsky, 1978 / 1930) that takes into account the characteristics of 21st Century mass media structures, agency and practices.