In this qualitative research study, I examine the literacy practices of five families who resided in a homeless shelter with attention to the complexity of literacy as it is taken up for fulfilling cultural and social goals within families, neighborhoods, and communities. Literacy is complicated through the lens of literacy sponsorship (Brandt, 2001) to suggest the differential access people have to literacy and the power sponsors have to sanction particular forms of literacy while dismissing existing literacies that families use in their everyday lives, but are undervalued in schools and the marketplace. Data collected from parent interviews and a family literacy program at the shelter shape the counterportraits (Meyer, 2010) intended to challenge the official portrait of homelessness. The analytical tool of dialogical narrative analysis (Frank, 2012) aided my identification of stories in the interviews that illustrated how parents perceived their lives before coming to the shelter, at the shelter, and how their lives would change beyond their stay at the shelter. The notion of "capital D" Discourses (Gee, 2005) supported my examination of how the parents engaged in overlapping Discourses that allowed them to contest deficit perspectives pervasive in the official portrait. The resulting counterportraits suggest that the official portrait is largely dismissive of the social problems associated with stark inequality in U.S. society. Complicating the role of literacy within this larger context of inequality is necessary to understand the wide gulf between the official portrait and the counterportraits represented in this report.