Climate risk means different things to different people depending on their circumstance. To smallholder farmers from sub-Saharan Africa (SSA), drought might mean food insecurity, temporary migration or famine; to a large-scale commercial farmer from the West, drought might mean opportunity – as per higher commodity prices, or a time to mind investments, or to seek government support. In this chapter, we aim to make a ‘two tail’ analysis of how risk affects farmers operating under contrasting socio-economic circumstances, and discuss likely options and opportunities for the sustainable intensification of maize-based farming systems.