One fundamental goal of learning is preparation for future learning (PFL) and being able to extend acquired skills and problem-solving strategies to different domains and environments. While substantial research has shown that PFL can be accelerated by obtaining metacognitive skills or influenced by the individual's motivation, no prior work investigated whether the interaction of the two factors could assess students' competency for PFL. In this chapter, we tackle this research question in one type of highly interactive e-learning environment, intelligent tutoring systems. More specifically, we investigate whether the combination of metacognitive skills and motivation would assess students' learning abilities in logic, and their competence to extend these abilities to a subsequent domain, probability.