This study examines the challenges and opportunities of school-to-work transitions in an Italian mountain area classified as rural, focusing on their impact on school dropout among young people. Conducted by the Youth Observatory (Osservatorio Giovani) of the Istituto Giuseppe Toniolo and by the Provincial Institute for Educational Research and Experimentation (Istituto provinciale per la ricerca e la sperimentazione educative; IPRASE), it adopts a participatory action research design in two phases: quantitative and qualitative. In the quantitative phase, an online questionnaire explores academic motivation, skill development, future aspirations, and educational trajectories of secondary school students and a group of young people who have turned to the PES. Special attention is given to the effects of work-based learning experiences on student engagement, investigating both risk and protective factors in the transition from school to work. Socio-demographic data are also gathered to contextualize outcomes and detect dropout patterns in rural environments. The qualitative phase consists of 20 focus groups: 18 with secondary school students from different educational tracks and 2 with young people who have experienced difficulties transitioning to employment and are currently NEET. These discussions capture participants' perceptions of work-based learning programs, including alignment with labor market demands, the role of mentors and support networks, and how these experiences influence persistence in school and career aspirations. Thematic analysis is employed to interpret the qualitative data, highlighting shared experiences, protective factors, and perceived barriers. By engaging stakeholders in continuous dialogue, this research aims to develop more inclusive and effective educational and vocational programs, ultimately reducing dropout rates and fostering youth employment. It contributes to understanding the roots of educational disengagement while advocating for policies that support student retention and professional development.