Background: Youth psychosocial and school adjustment results from complex developmental transactions between their individual characteristics and diverse environmental influences, which appear as risk or protective factors throughout one's development. Objective: From an ecosystemic and developmental perspective, this study aims to: (1) identify risk profiles among 13-year-old adolescents, and (2) associate these specific profiles with school dropout risk and substance abuse at age 15 years. Method: Data comes from a large Canadian study, the Quebec Longitudinal Study of Development through which adolescents (n = 1312) answered questionnaires at 13 and 15 years old. Results: First, through latent profile analyses, five profiles were identified based on individual, family, social, and school-based risk factors. Some profiles present higher levels of risk factors, while others comprise risk factors that are under the sample average level. Higher-risk profiles show stronger longitudinal associations with later adjustment difficulties. Conclusions: The findings help provide a deeper understanding of how the co-occurrence of various risk factors in adolescence is associated with later adjustment. The combination of the developmental psychopathology and ecosystemic frameworks, as well as the person-centered approach allowed by the latent profile analyses, helps shed new light on individual and developmental risk.