Researchers have noted the need, particularly when working with young people, to examine positive processes of development and how they can be considered protective factors of child development under adverse conditions. This study aims to investigate whether high levels of hope and life satisfaction during childhood are associated with a reduced risk of developing mental health problems and academic difficulties 5 years later. Measures of hope, life satisfaction, stressful life events, mental health, and students' engagement were administered to 367 students on two occasions, separated by 5 years. Results showed that participants with lower levels of hope and life satisfaction who experienced several stressful events had a higher risk of developing diminished mental health and difficulties of school engagement 5 years later, while those with higher levels of hope and life satisfaction were not exposed to this vulnerability. These findings reveal that hope and life satisfaction operate as protective psychological strengths in the transition from childhood to/and during adolescence.