Considerable attention has been paid to the benefits that urban trees provide and recent research has focused on how the distribution of trees in the urban landscape is affected by socioeconomic processes like social stratification, as indicated by associations with income, race, ethnicity, and education. These studies have found marked disparity in urban canopy cover, with primarily low income and minority neighborhoods commonly being underserved. However, few studies have investigated the potential to overcome urban canopy inequities through urban planning and reforestation. This question becomes even more important as many U.S. cities pledge to increase urban canopy cover as part of larger climate change mitigation strategies. Can today’s heavily developed U.S. cities use these tree planting initiatives to increase equity in urban canopy cover while still providing the infrastructure and housing necessary for expected population growth? This case study characterizes the socioeconomic drivers of the current urban canopy cover in Boston, Massachusetts, and further explores the possibility of distributing trees to increase equitable access to environmental justice and ecosystem services, while meeting housing and infrastructure needs. Results suggest that even when tree planting initiatives focus specifically on increasing canopy cover for environmental justice communities, equitable distribution of urban trees is difficult to achieve. Our findings indicate that difficulties arise not only from the expected policy and funding aspects, but also from ecological ones, including the physical availability of tree planting sites in environmental justice communities.