["Psychology in the Schools, EarlyView. ", "\nABSTRACT\nDifferences in school culture and context can shape how student well‐being influences learning outcomes. This study addresses this gap by examining the relationships between psychological and social well‐being domains and English learning outcomes across Indonesian general and Islamic schools. Using multigroup structural equation modeling (MGSEM) with a sample of 1319 students (General; n = 726; Islamic: n = 593), the study confirmed a universal positive correlation between happiness and learning, and a negative association between bullying and achievement. However, its main contribution lies in revealing context‐specific patterns that challenge universalist assumptions about student well‐being and learning. Happiness and peer belonging were significantly linked to higher motivation and lower anxiety only in general schools. Interestingly, optimism, although higher among Islamic school students, showed no significant relationship with any learning outcomes, revealing a novel “optimism paradox.” The pathways through which bullying influenced students also varied, showing stronger direct effects on achievement in general schools. These findings provide robust empirical evidence that the relationship between well‐being and learning is feasibly shaped by cultural and institutional contexts."]