As urban populations expand and climate change increases incidents of extreme weather, cities need sustainable ways to mitigate and adapt to these effects while supporting the health of their populations. Urban trees are a critical component of climate resilience and public health, but tree maintenance can be expensive and often beyond strained municipal budgets. Pruning trees in urban landscapes, especially early in a tree’s life, can result in savings over the long term. To prune a young tree effectively, minimizing injury to the tree and maximizing structural and environmental benefits, requires a combination of knowledge and skills. Municipalities have different ways of meeting this demand for skilled labor, and these decisions affect the outcomes for the health and longevity of the urban forest. To define the population of municipal workers who are pruning trees and determine the qualities and quantity of the tree pruning training they receive, I surveyed tree wardens throughout Massachusetts for information about pruning cycles, the workers pruning trees, and training the workers receive. Using research-based best practices, I developed a rubric that can be used to analyze training for essential instructional elements. The survey established that both Massachusetts tree wardens and pruning workers have a range of backgrounds. A large proportion of pruning workers are not arboricultural professionals, and this underscores the importance of effective training. Most training occurs on-the-job, led by a certified arborist. The fusion of the existing content-area expertise of the trainer with instructional techniques will result in more effective training with better outcomes for municipal trees. Successful training elements can be generalized and applied in other locations, resulting in a healthier, more mature urban canopy, a concomitant increase in environmental benefits, and cost savings that can be reinvested in urban forest management.