In this paper, we revisit different theoretical and conceptual issues that have been influencing the design of educational technology artefacts. In particular, we take into consideration recent perspectives in cognitive science that acknowledge the important effects of external representations (ERs) in learning and discuss the challenges regarding the applicability of these ideas in connection to seamless-learning environments. Extending the previous work revised here, this paper suggests that in order to further understand the nature of learning in these novel contexts, research needs to investigate how socio-affective factors come to the fore and influence the co-construction and use of ERs 'in the wild'.