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The Illegal Town Plan aims to understand and develop community- based futures for economic and social development. This case study describes and analyses an ongoing practice-based research project that began in 2015. The project, ambitious in its scope, has engaged with communities that have been stripped of power to develop and present new visions of their hometown. Located in Rhyl, North Wales, the design team has developed strategies, ideas, and possibilities with the people who rejected a European future. This project proposes a form of economic, architectural, and design speculation that aims to reimagine regeneration in a post-BREXIT Britain. The case study questions how we, as designers, evolve and develop processes and practices, popularised through the evolution of Critical and Speculative Design (CSD), to think through alternative social, political, and economic futures. The project utilises open, interdisciplinary, and diverse dialogues with the intention of building a heightened notion of engagement and agency. We hope to demonstrate practices that allow speculation to become democratised away from the gallery and into the world. Through conversation with two politicians, the authors were confronted by a growing realisation that there was a deep problem at the heart of regional development. There was a gap, a schism, between the community and those tasked with the future of their economic prosperity. For the last four years, we’ve been trying to support the people of Rhyl to bridge this gap. As a form of participatory speculation, this project aims to build a new language and discourse of speculation in which underrepresented voices become key to the ambitions of a small town and where the outlier is valued for opening alternatives. There have been many criticisms of critical and speculative design approaches in recent years. This project builds on nearly two decades of CSD experience (in both research and education) to imagine the evolution of the approach. Through a process of anecdotalisation, this case study gives four semi-fictional accounts of extraordinary moments that aim to give insight into the unseen process of an experimental design practice.