Trees on farms have the potential to improve the livelihoods of smallholder farmers. In addition to ecosystem services, they provide opportunities for generating additional income and contributing to household nutritional requirements. Despite these benefits, tree planting in the eastern drylands of Kenya has had many challenges, especially characterized by low seedling survival. This is partly due to erratic rainfall, planting of ecologically unsuitable tree species, poor quality seedlings, and poor tree seedling management practices. To support farmer learning to enhance tree seedling survival, 1600 farmers in Kitui, Machakos and Makueni Counties conducted on-farm planned comparisons to explore the performance of different planting and management practices on survival. The objective was to determine how different planting and management practices influence tree seedling survival across varying farm contexts. Farmers compared two sizes of planting holes with and without manure, and mulch. Seedlings of six tree species were planted in November 2016 and November 2017 and seedling survival was monitored six months after planting using electronic data entry. Data was analysed using R statistical software. Results showed that of the six tree species, Moringa oleifera seedlings had the highest survival rate in Kitui County while Carica papaya and Senna siamea had the highest survival rate in Machakos and Makueni Counties respectively. Seedlings planted with manure had a higher survival rate across all species and Counties. Azadirachta indica, Carica papaya, Mangifera indica , Melia volkensii, and Senna siamea had higher survival with the addition of mulch across all the Counties while seedlings planted in a woodlot had a higher survival compared to those planted along the boundary, scattered in cropland, along the terraces, and home compound. Survival was highest with watering in Makueni County while survival was higher for seedlings planted without fertilizer in Machakos and Makueni Counties. Seedlings planted in the 90cm by 90cm by 45cm hole had a higher survival rate than those planted in the 45cm by 45cm by 45cm. Survival was also higher in Kitui and Makueni Counties for seedlings planted in November 2017 compared to those planted in November 2016. Farmers reported that higher seedling survival was due to increased rainfall during the November 2017 planting season, improved farmer management of the seedlings due to practices learned during trainings, and changes in attitudes towards the value of tree planting which resulted in better management practices. Contextual variables affecting seedling survival include: household characteristics such as farm size, access to labour and inputs, and farm characteristics such as erosion status, soil quality and level of degradation.