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After five hundred years of historical development, Havana, Cuba remains one of the most complex and understudied American cities in the hemisphere. Founded in November of 1519, the city has been a multi-layered and continually renegotiated space for centuries. Havana co-evolved over the years with the Caribbean region, the Atlantic World, and the Spanish Empire, and later the empire of the United States. Known to the Spanish as “llave del nuevo mundo” (key to the New World), Havana’s centrality to the Spanish colonial enterprise in the Americas from its founding to 1898 enriched a city at the lynchpin of the Spanish treasure fleets. The city became a nineteenth-century slave society and a major center for sugar exportation, before serving as the political capital and performative stage for the Cuban republican and revolutionary governments in the twentieth and twenty-first centuries. Havana's architecture is legendary, and its buildings have shaped the spaces of urban life and identity. The city’s diverse, multi-layered, renegotiated, and repurposed architecture and spaces combined with its extensive documentation in Spanish and Cuban archives, travel accounts, memoirs, and newspapers invite researchers in visual and material culture studies to investigate one of the richest urban environments in the Americas. In spite of the ongoing challenges to research on various fronts, scholars in recent years have been forging ahead and opening up new understandings of Havana's material history. This session highlights new research as it fosters critical reflections on the evolution of the urban palimpsest of Havana after five centuries.