Many population centers in the American West rely on water from the Colorado River Basin, which has faced shortages in recent years that are anticipated to be exacerbated by climate change. Shortages to urban water supplies related to climate changes will not be limited to cities dependent on the Colorado River. Considering this, addressing sustainable management of water supplies is timely and critical to the long-term success of populations facing supply shortages and quality issues. Engaging in sustainability transitions of these hydro-social systems will increase the ability of such systems to meet the water needs of their populations. We identify historical transitions in water management and examine their context for three sites in the Colorado River Basin (Denver, Colorado, Las Vegas, Nevada, and Phoenix, Arizona) to provide insight for intentional transitions towards sustainable, or “water sensitive,” cities. The comparative historical approach employed allows us to more fully understand differences in present-day water management decisions between the sites, identify past catalysts for transitions, and recognize emerging patterns and opportunities that may impact current and future efforts in the Colorado River basin and beyond to transition to water sensitive cities.