Green infrastructure is a general term referring to the management of landscapes in ways that generate human and ecosystem benefits. Many municipalities have begun to utilize green infrastructure in efforts to meet stormwater management goals. This study examines challenges to integrating gray and green infrastructure for stormwater management, informed by interviews with practitioners in Cleveland, OH and Milwaukee WI. Green infrastructure in these cities is utilized under conditions of extreme fiscal austerity and its use presents opportunities to connect stormwater management with urban revitalization and economic recovery while planning for the effects of negative- or zero-population growth. In this context, specific challenges in capturing the multiple benefits of green infrastructure exist because the projects required to meet federally mandated stormwater management targets and the needs of urban redevelopment frequently differ in scale and location.