The question that motivates the discussion at the heart of this paper is how can we use technology to help learners (and teachers, peers and parents) to adapt the resources they find within a particular location to best support their learning needs. We present a description of a learning context as a Learner Centric Ecology of Resources and associated Organising Activities that can be deployed variously but with a concern to promote and support mediations, including those of the teacher and learner. For theoretical grounding, we look to sociocultural theory and in particular the Zone of Proximal Development (ZPD) with its emphasis upon the internalization of the interactions that occur within a learner’s context. This internalization process results in the decontextualization of social interactions within the head of the individual. It means that the resultant internal processes are defined by the context from which they originate. The ZPD can be thought of as a context in which productive interactivity can take place. The constructs of, situation definition, intersubjectivity and semiotic mediation as presented by Wertsch are explored in order to extract a specification of context for use in the design and evaluation of learning technologies. Likewise, the Zone of Available Assistance, the Zone of Proximal Adjustment and the Broadband Learner Model: all previously used by us to inform the development of educational software.