In this paper, we describe an approach and a prototype to enable participatory, collaborative tailoring of and within a groupware application. Our approach suggests extending the architecture of collaborative tools beyond just offering functionality to customise or tailor them to fit a use scenario. A process-oriented perspective on the (re-)configuration of the software should also be offered, together with the necessary features and interfaces. We describe principles and a prototype for this kind of enhancement using the example of configuring “Awareness” functionality in a groupware application. We comment on related future options to build collaborative applications that are “Redesign-aware”.