Over the past three decades, the world's irrigation sector has been increasingly exposed to decentralization and privatization. Many countries have embarked on a process to transfer the management of smallholder irrigation systems from government agencies to local management entities (Vermillion, 1997). This process of irrigation management transfer (IMT) includes state withdrawal, promotion of water users' participation, development of local management institutions, and transfer of ownership and management. South Africa has only recently initiated IMT in government smallholder irrigation schemes located in former homeland areas and most transfer operators are still unsure about how to design and implement the process. The objectives of the approach presented here is to contribute to investigating the sustainability of SIS in the context of IMT and to accompany and support decisions and actions undertaken by development operators by promoting collective solution seeking through scenario-testing. This chapter limits itself to a presentation of the approach and its principles, the model's conceptual framework and results from a case study.