Urban tree planting initiatives (TPIs) have become a prominent form of public work that has the potential to increase the livability and sustainability of cities. However, if not sufficiently resourced and thoughtfully planned and implemented, these high-profile programs may fail to achieve intended goals. To promote successful implementation of TPIs, we offer recommendations for the pre-planting, installation, and post-planting phases. During each of these phases we present five cross-cutting themes: ensuring adequate funding for all project phases; cultivating place-based landscape design; engaging and investing in communities; implementing sound planting practices; and evaluating performance and adapting over time.