Through a mixed methods approach, this paper explores young people’s perceptions about critical issues in secondary school and the improvements being made to prevent dropout risk. The empirical data were gathered from a representative sample of young people (14–24) in a socioeconomic disadvantaged region in the European Union. A principal component analysis assessed the most significant indicators that influence young people’s scholastic experience and effectiveness of education. A content analysis was applied to identify the key critical issues and possible strategies to support young people’s school satisfaction. The findings reveal a set of key indicators: interpersonal relationships; learning process; teacher role; school management; the impact of new technologies.