Recent research identified twenty conditions that enable the participation of smallholder tree growers in timber value chains. This paper builds on that work. It delves deeper into how and when during the plantation investment cycle these conditions facilitate sustained trade between small-scale timber producers, processors, buyers, and other service providers. It also identifies the stakeholders who are in the best position to influence these conditions. Conditions that affect access to smallholder timber such as biophysical characteristics of the land, characteristics of the plots where trees are planted, and infrastructure have important implications for trading partners. A buyer’s willingness to purchase smallholder timber also depends on timber quality and quantity, and reliability of supply. These are affected by conditions such as the availability of good genetic material, biophysical characteristics of land, and application of the right silvicultural practices. Building a viable value chain involving smallholder tree growers depends on matching the capabilities and aspirations of smallholders with the requirements of processors and buyers. Opportunities for smallholder tree growers to benefit from growing timber demand are on the rise, but successful engagement of small-scale timber producers with these markets will depend on how well all value chain agents connect and understand each other’s needs.