Framed by the existing theoretical and empirical research on cognitive and intelligent tutoring systems (ITSs), this commentary explores two areas not directly or extensively addressed by Akhras and Self (this issue). The first area focuses on the lack of conceptual clarity of the proposed constructivist stance and its related constructs (e.g., affordances, situations). Specifically, it is argued that a clear conceptualization of the novel constructivist stance needs to be delineated by the authors before an evaluation of their ambitious proposal to model situations computationally in intelligent learning environments (ILEs) can be achieved. The second area of exploration deals with the similarities between the proposed stance and existing approaches documented in the cognitive, educational computing, and AI in education literature. I believe that the authors are at a crossroads, and that their article presents an initial conceptualization of an important issue related to a constructivist-based approach to the computational modeling of situations in ILEs. However, conceptual clarity is definitively required in order for their approach to be adequately evaluated and used to inform the design of ILEs. As such, I invite the authors to re-conceptualize their framework by addressing how their constructivist stance can be used to address a particular research agenda on the use of computers as metacognitive tools to enhance learning.