The Romans were perhaps the most impressive exponents of water resource management in preindustrial times with irrigation and virtual water trade facilitating unprecedented urbanization and socioeconomic stability for hundreds of years in a region of highly variable climate. To understand Roman water resource management in response to urbanization and climate variability, a Virtual Water Network of the Roman World was developed. Using this network we find that irrigation and virtual water trade increased Roman resilience to interannual climate variability. However, urbanization arising from virtual water trade likely pushed the Empire closer to the boundary of its water resources, led to an increase in import costs, and eroded its resilience to climate variability in the long term. In addition to improving our understanding of Roman water resource management, our cost-distance-based analysis illuminates how increases in import costs arising from climatic and population pressures are likely to be distributed in the future global virtual water network.