In urban and suburban areas, stormwater runoff is a primary stressor on surface waters. Conventional urban stormwater drainage systems often route runoff directly to streams and rivers, thus exacerbating pollutant inputs and hydrologic disturbance, and resulting in the degradation of ecosystem structure and function. Decentralized stormwater management tools, such as low impact development (LID) or water sensitive urban design (WSUD), may offer a more sustainable solution to stormwater management if implemented at a watershed scale. These tools are designed to pond, infiltrate, and harvest water at the source, encouraging evaporation, evapotranspiration, groundwater recharge, and re-use of stormwater. While there are numerous demonstrations of WSUD practices, there are few examples of widespread implementation at a watershed scale with the explicit objective of protecting or restoring a receiving stream. This article identifies seven major impediments to sustainable urban stormwater management: (1) uncertainties in performance and cost, (2) insufficient engineering standards and guidelines, (3) fragmented responsibilities, (4) lack of institutional capacity, (5) lack of legislative mandate, (6) lack of funding and effective market incentives, and (7) resistance to change. By comparing experiences from Australia and the United States, two developed countries with existing conventional stormwater infrastructure and escalating stream ecosystem degradation, we highlight challenges facing sustainable urban stormwater management and offer several examples of successful, regional WSUD implementation. We conclude by identifying solutions to each of the seven impediments that, when employed separately or in combination, should encourage widespread implementation of WSUD with watershed-based goals to protect human health and safety, and stream ecosystems.