People experiencing any length of homelessness exhibit resilience and ingenuity in navigating geographies of street-level survival, in which food features prominently. The concept of ‘foodscapes’ has illuminated complex and often contradictory spatial and relational constructions embedded in food procurement routines (Miewald and McCann, 2014). On one hand, places of food provision offer spaces of refuge and socialization that contribute to a positive sense of well-being in an otherwise inhospitable urban environment. However, the availability and culture of services can maintain revanchist patterns of marginalization, exacerbating food insecurity and negatively influencing health and well-being (Pettes et al., 2016; Tarasuk et al., 2008). This paper investigates these contradictory geographies within an exceptionally vulnerable urban population, examining the dynamics and consequences of shifting foodscapes among people in transition from frequent and prolonged incidences of homelessness into independent housing.