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Formal schooling is widely recognized as the primary legitimate route to intergenerational transmission of (dis)advantages. However, less literature addresses how the proximate settings and latent (or informal) processes in education can mediate the relationship between family and educational outcomes. This study focused on two important but often overlooked themes in the ecology of education – interpersonal relations and out-of-school time. Applying structural equation modeling with propensity score weighting, this study revisited educational (in)equalities through the interplay between family background, student-teacher relation, out-of-school time curricular learning, and academic performance. The study centered on indirect effects to reveal latent mechanisms of intergenerational transmission of (dis)advantages in education. Moreover, the study approached the intergenerational transmission with a focus toward the diversity of student population.