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ABSTRACT: This study investigates the role of social capital and informational networks in undermatching, a phenomenon where students from underrepresented backgrounds enroll in less selective colleges than their academic profiles warrant. The paper focuses on urban high school students, seeking to understand how school contexts influence college choices and how schools can transition from perpetuating undermatching to mitigating it. Drawing on qualitative research from a case study in a high-poverty urban district, the study uncovers gaps in college knowledge among students, constrained counseling, and fragmented policies as critical issues. The research suggests a need for tailored, holistic college counseling, thus providing a base for policy reforms and technological innovations to combat undermatching and promote educational equity.