Since poverty is particularly concentrated amongst smallholder farmers, development programs intend to support rural livelihoods and agricultural entrepreneurship. The final impact of these programs remains, however, rather limited due to insufficient understanding of key challenges that smallholder families are facing. Many well-intended initiatives for reinforcing smallholder production systems and for strengthening their commercial relationships meet conceptual and practical limitations that reduce their effectiveness. Smallholder livelihoods are most constrained because behavioural drivers for adopting innovations and for upgrading value-chain relationships are not well understood and are frequently overlooked. This article discusses the analytical linkages between the key causes of smallholder poverty, the constraints that limit the effectiveness of ongoing rural development initiatives, and the prospects for alternative strategies to support behavioural change. A better understanding of what smallholders want and need may lead to fundamentally new policy propositions. It is argued that technological change in smallholder production or integration into market systems will only take place if embedded in behavioural change mechanisms that are complemented by appropriate institutions and governance regimes. This asks for coordinated structural reforms in farm and community organisation, value chain integration and more effective public-private cooperation.