Many cities recognize the potential of green infrastructure in managing and mitigating urban stormwater runoff (e.g. nutrient load), yet most lack systematic strategies for transitioning away from their existing conventional (gray) drainage systems. This project is intended to provide natural resource managers, planners, and engineers with decision support tools to aid the strategic planning process for transitioning to green infrastructure systems that emphasize trees and urban forests. First, a GIS-based mapping tool will help users identify areas suitable for green infrastructure, factoring in site conditions and existing drainage systems. Second, an optimization tool will help users identify an optimal mix of existing gray and new green infrastructure. A final decision support tool will help users select the preferred combination of gray and green options, given site constraints, water quality objectives, and key secondary social and ecological benefits of trees and urban forests (e.g. shade, heat-island mitigation, noise abatement). When used in combination, the proposed toolset will identify a prioritized, optimal transition pathway from gray to green infrastructure. The entire suite of tools will be supplemented with supporting documentation, including case studies in Tampa and Hillsborough County (Florida) and Milwaukee (Wisconsin).