This chapter aims to extend conversations around educational equity by emphasizing the role of community college contexts as a mediator between policy reform and student experience. Narratives of Tennessee (TN) Reconnect Grant recipients indicate that community college contexts related to advising and student support services and enrollment, transfer, and financial aid structures stand out as critical aspects for how TN Reconnect students engage once on campus. We pose recommendations for community colleges and community college leaders to better serve their adult students.