Numerous communities across America struggle with limited access to fresh produce and affordable, healthy foods, fueling a crisis in obesity and corresponding health complications. The conditions that give rise to these ‘food deserts’ are the product of commodified social, political, and economical structures that entrench barriers to access. To identify the challenges and opportunities to intervene, we conducted 33 semi-structured interviews, twelve in-home visits and shop-alongs with individuals from lower to middle income households living in an identified food desert. These findings highlight numerous strategies and shopper archetypes for the planning and purchasing of food with broad implications for food-agentic technologies. This paper shares strategies deployed by the food insecure to optimize food access, meal planning and budget constraints with corresponding design implications for a variety of technologies for food access. The benefits of technology have not accrued equitably, while efficiencies currently afforded by online shopping are less relevant to the food insecure. The aim of this paper is to contribute implications for the design of grocery shopping apps and highlight new opportunities to align these technological capabilities with human need to catalyze innovation in support of the greater good.