In this article, I draw on data from my qualitative dissertation study of the literacy practices of five families who resided in a homeless shelter to complicate the relationship between literacy, education, and inequality. Homelessness is examined through the lens of sponsorship to understand the differential access the families have to powerful sponsors of literacy and how schools and the marketplace may dismiss existing literacies that families use in their everyday lives. Their assimilation narratives reveal that the parents believed strongly in the promise of education to change the life trajectory of their children. Parents engaged in literacy for social and cultural purposes as well as middle class literacy practices that are valued in schools. Despite these attempts to assimilate, the parents and the children in the study did not benefit in significant ways and continually struggled against and resisted deficit perspectives surrounding homelessness and the inner city neighborhoods from which they came. The wide gulf between the official portrait of homelessness, largely defined by statistics and influenced by deficit perspectives, and the counterportraits that illustrate the lived realities of the families suggests educational reform must address the larger context of inequality in the United States.