It is believed that, with the help of suitable technology, learners and systems can cooperate in building a sufficiently accurate learner model they can use to promote learner reflection through discussion of their knowledge, preferences and motivational dispositions (among other learner characteristics). Open learner modelling is a technology that can help set up this discussion by giving the learners a representation of aspects of the learner as “believed” by the system. In this way/role, open learner modelling can perform a critical role in a new breed of intelligent learning environments driven by the aim to support the development of self-management, signification, participation and creativity in learners. In this chapter we provide an analysis of the migration of open learner modelling technology to common e-learning settings, the implications for modern e-learning systems in terms of adaptations to support the open learner modelling process,