The purpose of this study was to explore what factors facilitate and hinder meaningful connections among cultural brokers, parents, and teachers. We examined how trust and respect – or the lack thereof – manifested in relationships among cultural brokers, parents, and teachers; how trust and respect improved over time; and to what extent improved trust and respect between cultural brokers and teachers dismantled uneven power differentials between teachers and parents. During the 2013/14 school year, across five schools participating in a federal grant to support family engagement, we conducted over 30 semi-structured focus groups with English and Spanish speaking parents, paid parent volunteers, and teachers; interviews with Collaborators, school leaders, and project staff; and observations of grant activities. Focus groups and interviews included many of the same respondents in the fall and the spring in order to assess change. We supplement these data with quantitative data tracking parent participation in grant activities. We found that trust and respect were the foundation of meaningful connections among cultural brokers, teachers, and parents. Trust and respect among these groups improved through a combination of intentional relationship-building activities and more opportunities for these groups to interact regularly. . Despite these improvements, many teachers continued to harbor deficit-based attitudes toward parents. Our main conclusion is that increasing daily interactions between teachers and cultural brokers cannot undo the effect of hegemonic norms that characterize poor families, families of color, immigrant families, and single-parent families as lazy and uncaring at worst and simply unable to be good parents at best. Our findings reinforce the significance of the Dual Capacity-Building Framework for Home-School Partnerships, released by the Department of Education in 2014. Effective partnership between parents and teachers depends on simultaneous efforts to develop the capacities of both groups. We suggest a variety of practical strategies for achieving this goal.