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Tree planting is widely advocated and applied in urban areas, with large-scale projects underway in cities globally. Numerous potential benefits are used to justify these planting campaigns. However, reports of poor tree survival raise questions about the ability of such projects to deliver on their promises over the long-term. Each potential benefit requires different supporting conditions—relating not only to the type and placement of the tree, but also to the broader urban system within which it is embedded. This set of supporting conditions may not always be mutually compatible and may not persist for the lifetime of the tree. Here, we demonstrate a systems-based approach that makes these dependencies, synergies, and tensions more explicit, allowing them to be used to test the decadal-scale resilience of urban street trees. Our analysis highlights social, environmental, and economic assumptions that are implicit within planting projects; notably that high levels of maintenance and public support for urban street trees will persist throughout their natural lifespan, and that the surrounding built form will remain largely unchanged. Whilst the vulnerability of each benefit may be highly context specific, we identify approaches that address some typical weaknesses, making a functional, resilient, urban forest more attainable.