. 2018. Adaptive pathways and coupled infrastructure: seven centuries of adaptation to water risk and the production of vulnerability in Mexico City. Ecology and Society 23 (1) ABSTRACT. Infrastructure development is central to the processes that abate and produce vulnerabilities in cities. Urban actors, especially those with power and authority, perceive and interpret vulnerability and decide when and how to adapt. When city managers use infrastructure to reduce urban risk in the complex, interconnected city system, new fragilities are introduced because of inherent system feedbacks. We trace the interactions between system dynamics and decision-making processes over 700 years of Mexico City's adaptations to water risks, focusing on the decision cycles of public infrastructure providers (in this case, government authorities). We bring together two lenses in examining this history: robustness-vulnerability trade-offs to explain the evolution of systemic risk dynamics mediated by feedback control, and adaptation pathways to focus on the evolution of decision cycles that motivate significant infrastructure investments. Drawing from historical accounts, archeological evidence, and original research on water, engineering, and cultural history, we examine adaptation pathways of humans settlement, water supply, and flood risk. Mexico City's history reveals insights that expand the theory of coupled infrastructure and lessons salient to contemporary urban risk management: (1) adapting by spatially externalizing risks can backfire: as cities expand, such risks become endogenous; (2) over time, adaptation pathways initiated to address specific risks may begin to intersect, creating complex trade-offs in risk management; and (3) city authorities are agents of risk production: even in the face of new exogenous risks (climate change), acknowledging and managing risks produced endogenously may prove more adaptive. History demonstrates that the very best solutions today may present critical challenges for tomorrow, and that collectively people have far more agency in and influence over the complex systems we live in than is often acknowledged.