Despite several waves of interest worldwide in supporting smallholder farmers throughout the last 50 years, many smallholder farmers are still plagued by low profit margins due to their small scales and resulting high transaction fees, that is, if services are even available. In order to explore more deeply some of the systemic challenges and development approaches, this paper presents a case study analysis comparing two countries at different stages of development, Kenya and Mexico, and their logic behind supporting smallholder farmers. A literature review provides crucial background to understand the context, and a deep dive is taken into national strategy documents for the two countries. Further insights are developed from surveys and interviews with key informants in the countries. Recommendations for further research in the area are also provided.