Gender differences in exposure and reactivity to specific stressful life events (SLE) contribute to explaining adolescent boys’ and girls’ differential susceptibility to common adjustment difficulties like depression and behavioral problems. However, it is unclear whether these gender differences are also relevant to understanding another key marker of adolescent maladjustment: high school dropout. A state-of-the-art interview protocol was used to assess recent SLE in a sample of academically vulnerable Canadian adolescents (N = 545, 52% boys). The sample was comprised of three groups in approximately equal proportions: 1) students who had recently dropped out; 2) matched students at risk of dropping out but who persevered nevertheless; and 3) “normative” students with an average level of risk. When SLE of all types were considered together, overall exposure was similar for adolescent boys and girls, and the SLE-dropout association did not vary as a function of gender. However, gender differences emerged for specific events. Boys were especially exposed to SLE related to performance (e.g., school failure, suspension) and conflicts with authority figures (e.g., with teachers or the police), whereas girls were particularly exposed to SLE involving relationship problems with family members, peers, or romantic partners. In terms of specific SLE-dropout associations, one consistent result emerged, showing that performance/authority-related SLE were significantly associated with dropout only among boys. It therefore seems that considering gendered exposure and sensitivity to SLE is important for understanding the emergence of educational difficulties with long-ranging consequences for future health and well-being.