Promoting justice in therapeutic work with families demands an analysis of contextual factors such as race, ethnicity, gender, and social class in relationship to societal systems of power, privilege, and oppression. A broad understanding of these dynamics, however, is inadequate to inform our work with families whose social capital severely limits available life choices, social influence, and material resources. In this article, we describe working from a critical contextual perspective to consider how families gain and/or lose social capital through participation in multiple contexts. We introduce a technique for mapping social capitol within and across multiple systems as well as suggestions for interventions aimed at increasing the social well-being of low-status families. These include considering the dynamics of boundary crossing, recognizing and optimizing resistance to oppressive dynamics, finding ways to limit constraints and optimize opportunities, and developing webs of allies to support family functioning and access to resources. We offer the example of 13-year-old Pepe as a case in point.