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Using six cycles of Programme for International Student Assessment (PISA) data, this study examines trends in how school contextual effect, measured by school-level socioeconomic status (SES), influences adolescents’ expected occupational status in South Korea from 2000 to 2022. Results show that while family background consistently predicts expected occupational status, school SES effects have intensified over time, with the effect of school SES on occupational expectation consistently exceeding the effect of family SES across all cohorts. Quantile regression analysis reveals that school SES effects are strongest at lower distribution points of occupational aspirations. These findings suggest that school environments have become more decisive than family background in shaping students’ career goals, particularly for students with middle and lower occupational expectations.