Green infrastructure (GI) is one of the most common ways ‘nature’ is brought back into the city, but its justification and location is changing: city officials are realizing that ecological benefits alone are insufficient justification for GI, and that these urban greening projects must also address social concerns like equity and community values. GI is also increasingly being integrated into city streetscapes. To help understand this shift, this chapter looks at two cities – Toronto and Philadelphia – that have recently created policy and programs to support the integration of GI. Drawing from interviews with key stakeholders involved with the projects and analysis of media coverage and policy goals, the chapter examines the policy, people, and research that enabled the programs, as well as key successes, challenges, and lessons learned for each project. Key insights for implementation include the role of leadership and policy alignment; current tensions between bureaucratic frameworks, ecology frameworks, and community outreach; and potential options for creatively moving forward. The chapter concludes with a discussion of tensions and current limitations in measuring and understanding human health and well-being from an ecology and policy framework and suggests some options from research that may bridge these gaps.