This study focuses on the design and the implementation of a digital environment aimed at fostering strategic planning competence in problem-solving through individualization features: the Individualized Planned Strategy Environment (IPSE). Within IPSE, students are engaged in a sequence of oriented activities, guiding them in constructing and following a theoretically justified plan for solving a mathematical problem, thus promoting a gradual integration between conceptual and procedural knowledge. IPSE envisages also meta-level activities, aimed at fostering the handling of multiple representations toward a unifying and structural view of the subject at stake. We discuss the results of a case study conducted with engineering freshmen at the University of Salerno, involved in problem-solving activities devoted to peer assessment. This led us to identify certain student profiles both theory- and data-driven, according to the students' progress in using the components of Habermas' rationality when solving a problem. We highlighted that some students show a full realization of the dynamic nature of Habermas' model of rationality, where knowing, acting and communicating interact and intertwine.