Hypergraphic – Superstudio is a marriage of discrete terminologies aimed at forming a manifesto and pedagogic grouping. Such formation arises from what is to be argued as a representational crisis in Digital Landscape Architecture. Drawing (Digital & Analogue) involves an imaginative and speculative activity – of seeing possibilities. It is theoretical, abstract and also tactile – it arguably mediates between the conceptual and productive. Given the role that drawing plays within wider information design, paradoxically it has received little attention and research in Landscape Architecture. Given this lack of critical attention, it is worth forming new methods and new insights in this area leading towards a transdisciplinary digital landscape – for effective information systems.