This chapter explores how two European cities—Milan and Warsaw—adopted the same tools but contrasting governance strategies to address urban food insecurity during times of crisis. It examines how their distinct institutional mechanisms shaped not only their immediate responses but also their learning processes and the development of long-term resilience strategies. Both cities faced overlapping crises, or polycrises, with the COVID-19 pandemic as a common challenge. Warsaw, however, offers a particularly compelling case, as the war in Ukraine added further pressure on its food assistance systems and governance capacity. Adopting a decentralization-centralization lens, the chapter compares these two cases to shed light on how different governance models influence crisis management and the pursuit of integrated food security programs. The contrast between Milan’s innovation-driven, decentralized resilience and Warsaw’s efficiency-oriented, centralized approach highlights the importance of institutional maturity, resource allocation, multi-stakeholder collaboration, and the ability to integrate and reuse knowledge in navigating complex, compounded crises.