The USA is the only country in the developed world experiencing sustained declining life expectancy. This historic downturn has occurred over the past decade, driven not only by COVID-19 pandemic-related deaths but also by substantial increases in chronic disease and mortality from suicide and substance abuse (i.e., “Deaths of Despair” (DoD)). While medical education has traditionally struggled to address nutrition, social determinants of health (SDH), and preventive care—factors intimately interwoven with falling lifespan—educators must prepare students for this era-defining public health challenge. In leading a Food as Medicine (FAM) initiative at Penn State College of Medicine over the past decade, we have explored community-based strategies for helping healthcare trainees apply nutritional and preventive health knowledge with vulnerable community members, including those at risk for chronic disease and despair-related illnesses. In this chapter, we describe FAM programs staged in farmers’ markets, community gardens, hiking trails, senior centers, food banks, and mobile food units, and share benefits we have observed for both students and local residents. We ultimately argue that medical schools have a critical role to play in supporting the next generation of health professionals tasked with addressing the consequences of our current public health failures, and that FAM approaches can assist in this process.