A growing number of initiatives at global, regional and national scales propose to plant millions, billions or even trillions of trees as a simple solution to resolve complex environmental problems. However, tree planting is much more complicated than it seems. We summarize the multifaceted decision‐making process needed and offer guidelines to increase the success of the proposed ambitious efforts to increase tree cover world‐wide. Given the varied definitions of and motivations for tree planting, it is critical that stakeholders work together to clearly define the biophysical and socioeconomic goals of each project. Then a series of questions must be addressed about where and how (e.g. planting trees vs. allowing for natural forest regrowth) to most effectively achieve these goals and minimize unintended negative consequences, as well as how, when and by whom success of efforts will be evaluated. Key guidelines to successfully increase tree cover include: (a) first addressing the underlying drivers of deforestation; (b) integrating decision‐making across scales from local to global; (c) tailoring tree planting strategies to clearly stated project goals and planning, adaptively managing and evaluating success over a sufficiently long timeframe; (d) focusing on the forest ecosystem as a whole, and not just the trees; (e) coordinating different land uses and (f) involving stakeholders at all stages of the planning process. Synthesis and applications. Tree planting, along with other strategies to increase tree cover in appropriate locations and contexts, can make a valuable contribution to ensuring the ecological and social well‐being of our planet in coming decades, but only if these efforts are considered as one component of multifaceted solutions to complex environmental problems and are carefully planned, implemented and monitored over a sufficiently long time‐scale with stakeholder engagement and broader consideration of socio‐ecological complexities.