PCTOs (Pathways for Transversal Competencies and Orientation) are a strategic initiative in the Italian education system designed to foster the holistic development of upper secondary school students and support their educational and career choices. This PRIN 2022-funded project aims to analyze PCTOs’ characteristics and evaluate their impact on personal resources, student dispersion, and orientation outcomes. The research is structured into three studies. The first examines the inclusion and objectives of PCTOs within the Three-Year Training Offer Plans (PTOF) of 200 schools, assessing adherence to ministerial standards through document analysis. The second involves five case studies in Lazio, Lombardy, and Emilia-Romagna, gathering data from institutions, teachers, and students to explore factors influencing PCTO planning and outcomes. The third study surveys first-year university students to assess the long-term impact of PCTOs on career decisions and well-being. The project will culminate in an open-access digital platform to help schools self-evaluate and enhance their PCTOs. By integrating theoretical, educational, and technological insights, the project seeks to inform educational policies, improve practices, and foster collaboration within the academic community.