Climate change and environmental degradation are among the most pressing global issues, making tree planting initiatives essential for combating climate change, halting biodiversity loss, and restoring degraded landscapes. However, many tree planting programs face challenges such as planting non-native, potentially invasive species, and disregarding community preferences. This paper examines the determinants and challenges affecting tree planting programs, utilizing a unique dataset from northern Namibia. Using a multilevel logistic regression model, we found that low-income households with larger landholdings are more likely to participate in tree planting initiatives. In contrast, households with members engaged in nonfarm employment are less inclined to start or continue planting even when provided with seedlings, as they may prefer more stable and low-risk income streams. We recommend that future tree planting programs align with household preferences for tree purposes and provide sufficient economic incentives to ensure the sustainable maintenance of planted species.