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In France, artistic and cultural projects with incarcerated persons are undergoing fast development and are financed with conviction and commitment by ministries and relevant organizations, with no real capitalization on previous experience or reflexive analysis, and always with underlying doubt regarding their efficacy. This is the social and political problem that the “Evaluation of Cultural Experience during Incarceration” project aims to explore with experimentation by design. This article presents the question founding the research project; its stakes regarding reflexive and collective definition by design of the evaluation and of cultural experience while incarcerated, embodied in The Kiosque, an object promoting reading in detention; as well as the proposed methodology. There are two objectives: not only to contribute to sketching the epistemological borders of design but also to lay the foundations of an evaluation of artistic and cultural projects with incarcerated persons, evading the injunctions of quantitative measurement and thus re-establishing what makes stakeholders value these projects, and the value they hold in improving the habitability of the world.