Since the 1970s, the Kebili region southern Tunisia has undergone significant territorial changes due to the expansion of date palm plantations based on illicit boreholes tapping the underlying deep aquifers. These private initiatives, called “extensions”, have developed on collective unfarmed areas, outside historical oases and have raised sustainability concerns. To address the groundwater sustainability, local actors need to build a joint vision of on-going dynamics. The objective of this study is: (i) to analyse the trajectories of the oasis extensions, (ii) to give an overview of the socio-economic and the environmental drivers and (iii) to assess how local actors assess these extensions. The study builds on spatial analysis, on surveys and participatory workshops with actors of the region. The development of extensions was triggered by economic factors and based on innovative ways of accessing water, land, and energy. Extensions, that were first created on lands in proximity of ancient oases then spread further-out to other areas, can be described as spontaneous. Other were developed on lands located far from ancient oases, with the support of local councils in charge of land management. Actors have identified the overexploitation of groundwater as the main threat to the sustainability of the region, but no discussion has been initiated yet on how to deal with this threat. Results derived from this study could support discussions about the future of these areas.