Abstract-Problem solving is the skill that coordinates all the cognitive, metacognitive and behavioral processes taking place when individuals encounter a previously unprecedented situation or difficulty. Metacognitive processes seem to play the most important role for resolving a problematic situation as individuals reflect on their acquired knowledge, skills and experiences, thus become aware of their capabilities and how to regulate them. Therefore, metacognitive awareness is the competence that mostly assists individuals in their attempt to construct new knowledge and reach their goals. Furthermore, individuals' self-assessment and peerassessment processes could reveal their level of metacognitive awareness and therefore, by far, their problem solving competency. Consequently, ICTs could capture individuals' problem solving skills through tracking down and analyzing the latters' cognitive and metacognitive processes as well as their behavioral patterns. The aforementioned computerbased assessment could consist of a fuzzy expert system with domain knowledge from an automated task-based test with particular solution strategies in combination with log data for identifying and classifying one's level of problem solving ability according to specific criteria.Index Terms-problem solving skills assessment, collaborative problem solving skills assessment, life success.