Adolescents (santri) in Islamic boarding schools (pondok pesantren) encounter demands, including separation from family, rules, schedules, and interactions. While these environments aim to foster independence and character, they may create pressures affecting psychological well-being. This study investigates the effects of academic stress, emotional intelligence, and self-compassion on santri’s psychological well-being using Structural Equation Modeling (SEM). The sample consisted of 298 santri aged 15–18 years in Makassar, selected through cluster sampling. Data were analyzed using SPSS and SmartPLS. The findings show that academic stress negatively affects emotional intelligence (β = -0.274; p < 0.001), self-compassion (β = -0.200; p < 0.01), and psychological well-being (β = -0.139; p < 0.01). In contrast, emotional intelligence positively affects psychological well-being (β = 0.309; p < 0.001). Self-compassion does not have an effect on psychological well-being (β = 0.102; t<1.96). Mediation analysis shows that emotional intelligence mediates academic stress and psychological well-being (β = -0.085; p < 0.01), with partial mediation (VAF = 37.95%). Conversely, self-compassion does not mediate the relationship (t<1.96). These findings highlight the importance of strengthening emotional regulation based on Islamic values to enhance adolescents’ well-being within pesantren. Practically, boarding schools should integrate emotional intelligence training into pesantren curricula as a mental health strategy. Keywords: academic stress, emotional intelligence, psychological well-being, self-compassion