Since the inception of our bush-encroachment decision support system, we have gone through many cycles of adaptations while striving towards what we believed to be a usable system. A fundamental difference between community based users and individualistic users necessitates a change in the design and evaluation methods as well as a community agreement of concepts and values guiding the design. In this paper we share the lessons learned along the story depicting the metamorphosis of a bush encroachment decision support system in Southern African rangelands. Above and beyond community members participating in the design and evaluation of the system, they establish the community grounded values determining the system's quality concepts such as usability.