Background. The school environment influences a child’s well-being in different ways, not only by education but also by forming social roles, habits, and stress responses. It provides the sources of stress as well as the sources of resilience. Objective. This study examines the variety of coping strategies of adolescents attending different educational institutions and the different trajectories in the adaptation process in different educational environments. Design. This paper examined the coping strategies, optimism, and subjective well-being of students in different educational environments. Three schools were represented, and 646 adolescents between 12–17 years old participated in the study. The measures included the Ways of Coping Checklist, The Life Orientation Test, and The Warwick-Edinburgh Mental Well-Being Scale. Results. Coping strategies used by students attending different schools significantly differ in their intensiveness of use and age distribution. However, optimism and subjective well-being are higher among older adolescents and do not depend on the educational environment. Conclusion. The differences in the coping strategies preferred by the adolescents in different types of schools reflect their adaptation to the different environmental demands, which is confirmed by the same level of subjective well-being and optimism in different environments. However, their repertoires of coping strategies are not analogous: the students in high-rated schools use more various and more constructive coping strategies than students in low-rated schools. We may assume that their resilience and ability to cope with stress outside of school may also differ, which, in turn, can influence their further life trajectories and ability to cope with difficulties in life, perpetuating existing social inequality. Early and middle adolescents in all types of schools show a lower level of well-being and optimism than older students, which may indicate their higher psychological vulnerability and need for adult attention and support compared to older adolescents.