The agro-ecosystems of semi-arid and dry sub-humid SSA are inherently dynamic. At this point in time they are also experiencing a series of complex social–ecological changes that make their future even more uncertain. To ensure that development investments made today in the small-scale farming systems that dominate these regions make sense also in a long-term perspective they should benefit the local communities over a range of potential futures. We applied a participatory scenario planning approach to a smallholder farming community in semi-arid Tanzania, exploring four alternative development trajectories for the area, to increase the robustness of current investments in small-scale water system technologies. We found that water system technologies will be important across a number of possible futures, but that the most relevant target of these innovations, e.g., staple- versus cash-crop production, or individual- versus community-managed systems, differs. We argue that building capacity for experimentation among farmers is key to upgrading their farming systems, as this will generate benefits over a range of alternative futures. Furthermore, we found it to be essential across a range of scenarios to analyze the system-level impact of proposed interventions for successful investments in water system technologies. We conclude that although the method presents some challenges, participatory scenario planning is a useful tool for integrating research and development projects in the larger context, asit increases the understanding of events and processes that may either challenge the project or provide opportunities for it.