This chapter proposes that technologically enhanced learning should be understood and evaluated by means of a combination of analytical strategies. These will allow us to analyze it both as seen from the macroanalytical or “outside” perspective of a rich social, cultural, and technological context, and from a microanalytical or “inside out” perspective of individual sense-making in learning situations. As a framework, we will be using sense-making methodology, and a model for causal layered analysis. Our area of attention will be limited to the “remediated classroom” of constructivist, net-based university education. Problematizing some common assumptions about technologically enhanced learning, the authors define 10 questions that may serve as the basis for a research agenda meant to help us understand why the many visions and ideals of the online or remediated classroom are not more widely realized and demonstrated in educational design and practice.