The PCTO Social Cohesion and Urban Sustainability set in the framework of the MUSA-Spoke 6-Action 3.1.3 “Contrasting and prevention of early school leaving in disadvantaged urban neighbourhoods”. The paths aim to develop processes of social inclusion and to enhance cultural diversity. PCTO students have been involved in a team of researchers, professional educators, teachers, pedagogues, volunteers, PhD and university students, with a so-called Community service learning in the afterschool services of the QuBi network in the San Siro area. The research question explores on one hand, the opportunity provided to students by the extracurricular training program to reflect on their own life skills within a multiproblematic and multicultural context and, on the other hand, it examines the development of new skills, both among the students themselves and the children they support through individualized educational tutoring. A diachronic analysis of the student’s diaries maintained throughout the program reveals a development in their approach to the context and an increased awareness of their role in supporting children’s learning processes. This evolution also emerges in the two focus groups conducted by the researcher, midway through and at the end of the program, aimed at fostering a participatory reflection on their educational path.