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Families and schools are powerful forces for shaping students’ educational trajectories, yet the nature of their roles remains contested. On one hand, support from families and schools is lauded for its many benefits to students; at the same time, families and schools are also characterized as major sites of social reproduction. Such a duality raises a key question: how do families and school mitigate—but also magnify—educational inequality at once? To answer this question, we explore how family support and school support shape students’ college-going pathways and how these effects differ by socioeconomic status (SES). Our findings suggest that families indeed play a dual role in students’ college-going, combating disadvantage for lower-SES students and reproducing advantage for higher-SES students. Schools also combat disadvantage for lower-SES students, but not to the level of equalizing college-going. Altogether, our study contributes to our understanding of how social support shapes socioeconomic mobility and has implications for how schools and policymakers think about expanding educational opportunity.