Exploring past societies in different cultural contexts can offer insights on issues that are timeless and permanent, that is, challenges addressed in the past that remain relevant in the present and form questions for the future. One such global challenge is to maintain food security for all citizens in cities. This chapter draws on insights from pre-Columbian Maya cities, medieval Constantinople, and wartime London and applies these to the mega region of the contemporary Ganges-Brahmaputra Delta. It demonstrates the potential to integrate archaeological and historical research with investigations of contemporary conditions to inform the planning sector. Despite fundamental differences, urban and peri-urban food production continues to play a key role for food security and city resilience. The long-term record of dealing with challenges to food security suggests that it is essential to maintain a diversity of food systems including localised ones, and a capacity for institutional flexibility at multiple scales.