Stormwater management in the District of Columbia has evolved substantially over the past decade and continues to evolve in response to new and anticipated challenges. We look back at how stormwater management has changed, the supporting science, and the resulting shift in infrastructure. We also look forward to the next decade and identify current and anticipated challenges and discuss potential methods to address them. In 2013, DC published new regulations, initiating a shift from a stormwater management approach focused on treatment of the first flush to a retention-driven approach. A stormwater credit trading program was also established. For the past 10 years, this retention-driven approach has resulted in substantial growth of green infrastructure, distributed throughout the District. Over the next 10 years, stormwater infrastructure will need to contend with challenges from increasingly intense storms and flooding events, increased urban heat, and more. Current regulations can meet these needs to an extent, but further updates, based on best available science, are needed to ensure resilience over the coming decade and beyond.