In this chapter we describe the expert-based approach in evaluating Open and Distance Learning (ODL) environments. Our study is mainly concerned with the domains of Human-Computer Interaction (HCI) and Human Factors (HF), and the synergy between them in the field of ODL. The most promising approach to evaluating ODL is one which attempts to frame the ideas from distributed cognition research in a way that is more usable by HCI designers. Though the distributed cognition framework acknowledges a vast majority of cases suited to HCI designers and evaluators, it has never been tried before as a framework for the evaluation of the cognitive work that is distributed among people, between persons and artifacts, across time and between abstract resources of information in the ODL domain. So, the main contribution of this chapter is on one hand to present the contemporary research on the domain, and, on the other hand to pinpoint the main concerns and to propose trends for further research on this complicated field that combines ODL, HCI and HF in such a holistic manner.