Urban water systems across the United States are struggling to adapt to an evolving set of threats. Understanding specific pressures and the regional responses to those pressures requires input from practitioners with knowledge of sociotechnological aspects of urban water systems. The Urban Water Innovation Network (UWIN), a consortium of academic institutions and partners supported by the National Science Foundation Sustainability Research Network program, provides a unique opportunity to engage stakeholder and research communities across the U.S. Interactions between UWIN researchers and water stakeholders from five regions (Southeast Florida, Sun Corridor, Mid-Atlantic, Pacific Northwest, and Front Range) form the basis for case studies on transitions toward sustainability. Analysis of qualitative data on pressures, states, and responses collected during interactions provides insight into the challenging context of urban water management. Top pressures identified include climate change, aging infrastructure, water quality impairments, and funding limitations. Additionally, stakeholders described resistance to change and short-term perspectives among elected officials, limited understanding/awareness of water systems among decision makers, and lack of leadership on water issues as contributing to pressures. More than technological solutions, practitioners call for improved coordination in water management, strengthened communication with elected officials, and behavioral change among citizens. Regarding stakeholder-scientist interactions, participants sought practical outcomes, such as the organization of seemingly abundant scientific products into usable products. The utility of the pressure-state-response model as a framework for data collection and analysis in the context of understanding transitions toward urban water sustainability is discussed and recommendations for future studies are presented.