Over the past several years, shared drawing activity has emerged as a focus of research at Xerox PARC. Case studies of group design work, both in face-to-face and video mediated settings, initially revealed a need for providing a shared drawing capability to support distributed design work. Shared drawing activity has proven to be a topic of considerable complexity and subtlety. The talk will focus on a range of shared drawing prototypes that we have built and studied, and will show how the development of these systems has been grounded in studies of how people accomplish the social work of designing. Several prototypes will be discussed, ranging from Commune (a multi-user, computational sketching program), to VideoWhiteboard (a large- scale, video-based multi-user drawing tool). The various prototypes represent quite different approaches to supporting shared drawing activity. This variety has aided the development of both our understanding of the collaborative activity and the shared drawing prototypes themselves.