Conventional approaches to irrigation development involve large lumpsum investments in big infrastructure that cannot adapt to changing climate and socio-economic conditions. There is an urgent need for alternative ways of investing in smallholder irrigation in Sub-Saharan Africa (SSA) that are adaptive and avoid capital lock-in. Adaptive Investment Pathways (AdIP), inspired by the Dynamic Adaptive Policy Pathways (DAPP) concept, proposes stepwise investments to support smallholder irrigation development. AdIP builds resilience to future shocks through dynamic and flexible investment plans instead of investing in single static solutions. To develop an empirical grounding for operationalizing AdIP, we draw lessons from three case studies representing different stages of irrigation development along shallow sand river aquifers in Kenya and Zimbabwe. We retrospectively analyse the nature of investments at farm and landscape scales, and the type of risks and opportunities that farmers respond to. We find that in face of risks, farmers diversify their livelihoods, make small investments incrementally especially in response to opportunities and risks created by external triggers, and pause or reorient activity when they reach saturation points, i.e., biophysical or socio-political limits to their development objective, here irrigation development. Governments and external agencies can support smallholder irrigation development in SSA through targeted landscape scale investments that address saturation points faced by smallholders. This requires a robust participatory monitoring framework to identify and respond to saturation points, and a re-thinking of financing mechanisms which do not measure progress against a fixed schedule of investments, but instead measure continuous progress towards the development objective.