Federal initiatives place school counselors at the forefront of increasing college access for students in underserved communities. Although college enrollment rates have increased, low attainment rates persist in low socioeconomic communities and communities of color. Families in these communities aspire for their children to go to college but rely on the school counselor to help their child navigate the complex path to college. Although the high school counselor is ideally positioned to reduce barriers and engage families in the postsecondary process, they often lack the capacity and resources to do so. Thus, this action-oriented qualitative case study was conducted over 8 months, and explored how urban high school counselors engaged families as collaborative partners to address the metanarrative of low postsecondary attainment rates. Findings suggested that building trust within the school community as foundational to engaging families, taking simple actions were catalysts to transforming school culture, and leveraging family engagement increased school site capacity and affected the broader school community.