Urban tree cover is inequitable in many American cities, with low-income and non-white neighborhoods typically having the least coverage. Some municipal and non-profit tree planting programs aim to address this inequity by targeting low-income neighborhoods; however, many programs face lack of participation or resistance from local residents. In this study, we aimed to uncover the economic, social, cultural, and physical barriers that community leaders face in planting trees and fostering engagement in a neighborhood with low tree canopy. In collaboration with an urban greening nonprofit in Philadelphia, Pennsylvania (US), twenty in-depth interviews were conducted with community leaders in a low canopy neighborhood, North Philadelphia. Half of these leaders were already involved with local tree planting programs, while the other half were not. Findings reveal that despite broad appreciation for trees and greenspaces, there are concerns about the risks and costs residents assume over the course of a tree's life cycle, the threat of neighborhood development and gentrification associated with trees, limited plantable space, and limited time and capacity for community organizations. Additionally, these barriers to participation may be amplified among low-income and communities of color who face the legacies of historical tree disservices and municipal structural disinvestment. Addressing community concerns regarding the long-term care of trees beyond the initial tree planting would likely require further programmatic support. Overall, this research highlights the complexity of addressing inequities in tree canopy and the importance of integrating resident and community leader perspectives about disservices and management costs into tree planting initiatives.