Based on sexual revictimization theory, this study investigates the role of individual characteristics (e.g., depression and subjective well-being) and contextual factors (school and organized activities) in the development of sexual harassment revictimization among Swedish Grade 7 (46% girls; Mage = 14.09) adolescents who were followed over 3 consecutive years. The analytic sample comprises adolescents in the school context (T1 N = 678, T2 N = 563, and T3 N = 471) and in organized free-time activity contexts (T1 n = 443, T2 n = 400, and T3 n = 356). Our findings suggest that adolescents with experiences of sexual harassment victimization in Grade 7 were at an increased risk of being sexually revictimized the following 2 years across the two distinct developmental contexts. Further, our results reveal that adolescents are more sexually harassed by their peers in organized activity contexts both concurrently and over time if they were victims of sexual harassment in the school context and the other way around. The findings underscore the need for sexual harassment prevention interventions to consider different developmental contexts simultaneously and to focus on the history of adolescents' experiences of victimization. (PsycInfo Database Record (c) 2024 APA, all rights reserved).