Elastic Octopus was inspired by a perceived increased reluctance in student attitudes towards taking risks and failure in design innovation. In particular, recent trends in funding and risk-aversion in earlier phases of education where failures are discouraged has limited the potential for ground breaking innovative thinking. This experimental design project was conceived to tackle the failure reluctance trend by developing a team based cross-disciplinary masters level design innovation studio module where students would succeed in relation to their capacity to demonstrate failure. Principally this involved creating a permission giving process where ambitious design experiments are developed in order to encourage the transgression of edges and boundaries. This was achieved by adapting a number of creative design methods including blue-sky thinking, back casting and design exorcisms to challenge and de-programme failure aversion. Succeeding through failure involved transitioning from meta-themes through to experimental contexts where failures could be attempted as a way of exploring the limits of technologies, structures, mental models, human engagement and other factors critical to success. We hope that insights gained from this disruptive educational module can offer unexpected benefits for students ranging from increased failure resilience, through to narrative generation and context forming skills while at the same time providing wider value in discussing how designers deal with failure.