The use of open education resources and practices is seen as revolutionising contemporary teaching and learning. This can be seen in the ongoing shifts in research, curriculum design and pedagogical practices pushed for in digital learning. The study presented in this chapter focuses upon online learning sites from the perspective of posthumanism and postmodern pedagogy and its design builds upon self-ethnography and non-participant online ethnography. It has three aims: first, explicate the analytical assumptions in relation to online learning embedded in global Northern posthumanism theories in relation to the global Southern Indian communication theory of sadharanikaran; second, present an overview of features of contemporary online educational sites with the intent of illuminating the data that can be relevant for analysing some key spaces for learning; and third, present some preliminary findings on issues and challenges in contemporary online learning sites and highlight pedagogical approaches that emerge from the study.