In the current socioeconomic context, the transition from school to work has become a complex task, has a long-term impact on careers, and tends to emphasize social inequalities during the labor market integration process. Succeeding in this transition implies not only finding a job when leaving school but also accessing decent and dignified work—namely, a job that is both secure and consistent with young adults’ expectations of working life. Social, institutional, and psychological factors influence the school-to-work transition (STWT) process and its outcomes. Consequently, promoting successful STWTs involves both contextual and psychosocial interventions. Contextual initiatives imply the promotion of education systems that facilitate smooth and inclusive transitions from school to work as well as labor market policies that protect young adults from job insecurity. Psychosocial interventions should foster young adults’ transitional resources and help them access organizations offering work settings that fit their expectations.