School transitions represent critical processes in students’ educational journeys, as they involve significant changes requiring adaptation to new environments, relationships and learning methods. These transitions occur within a complex system where individual, family, school, and environmental factors interact. If managed properly, transitions can promote academic success and well-being; conversely, if neglected, they can lead to failure. These processes affect not only academic performance but also students’ perceived well-being, which plays a crucial role: it can act as a predictive factor facilitating adaptation or as an early indicator of difficulties. The literature highlights how a high level of well-being promotes resilience, motivation and school integration, while low well-being is associated with greater risks of anxiety, isolation and school dropout. For many adolescents, moving to a new educational level represents an opportunity for growth; however, for others, it can be a source of stress and discomfort. Transition difficulties are often more pronounced among students with a migrant background, who face linguistic, social, and relational barriers. This contribution explores the school transition difficulties and well-being of native and migrant students enrolled in Vocational Education and Training (VET) pathways. Two distinct scales were employed: one to explore the perceived difficulties and another to investigate satisfaction and school climate. The results confirm the crucial importance of promoting school well-being as a key factor in effectively supporting students’ adaptation during transition phases. The evidence underlines the importance of educational and support strategies aimed at promoting students’ well-being, with particular attention to cultural specificities and individual needs.

Keywords: School transition difficulties, school well-being, accademic success, migratory background, VET.