Promoting forest regeneration outside protected forests is an urgent challenge in densely settled, biodiverse areas like the East African Rift. Regenerating forests entails managing complex processes of ecological recovery as well as understanding the needs and motivations of local land users. Here, we evaluate pathways for attaining native tree regeneration across variable site conditions. We investigate two common strategies for attaining native tree regeneration—setting aside land for forest regeneration (‘Protect and Wait’) and native tree planting (‘Native Tree Planting’)—and a possible third, smallholder exotic tree-planting (‘Woodlots’). We measured native seedling regeneration patterns for each of the three strategies, all underway at a single site in Southern Tanzania. We also used historical aerial photograph analysis and interviews with smallholder farmers to understand past and present land use. Our results show that forest regeneration has been arrested for decades on land under ‘Protect and Wait’, and seedling survival appears to be limited under ‘Native Tree Planting’. In contrast, we found saplings of 28 native species growing spontaneously within pine, eucalyptus, and cypress woodlots planted <400 meters from native forest boundaries. Interviews showed that the citizens most likely to plant woodlots near the protected forest were those who owned additional land parcels elsewhere. Some saw woodlots as a means to avoid losing crops to wildlife at the forest edge. Our findings suggest: 1) Simply setting aside land for regeneration does not guarantee forest regrowth, even if it is adjacent to natural forest, 2) native seedlings will be more likely to survive if planted near shade trees, and 3) smallholders’ woodlots could hasten native tree regeneration at forest park edges if farmers have incentives to protect the native tree seedlings in their woodlots and they can find land elsewhere to plant food crops.