In this article, we present a lifecycle study of We Dare You, a substitutional reality installation that combines visual and tactile stimuli. The installation is set up in a center for architecture, and invites visitors to explore its facade while playing with vertigo, in a visual virtual reality environment that replicates the surrounding physical space of the installation. Drawing on an ethnographic approach, including observations and interviews, we researched the exhibit from its opening, through the initial months plagued by technical problems, its subsequent success as a social and playful installation, on to its closure, due to COVID-19, and its subsequent reopening. Our findings explore the challenges caused by both the hybrid nature of the installation and the visitors’ playful use of the installation which made the experience social and performative—but also caused some problems. We also discuss the problems We Dare You faced in light of hygiene demands due to COVID-19. The analysis contrasts the design processes and expectations of stakeholders with the audience’s playful appropriation, which led the stakeholders to see the installation as both a success and a failure. Evaluating the design and redesign through use on behalf of visitors, we argue that an approach that further opens up the post-production experience to a process of continuous redesign based on the user input—what has been termed design-after-design—could facilitate the design of similar experiences in the museum and heritage sector, supporting a participatory agenda in the design process, and helping to resolve the tension between stakeholders’ expectations and visitors’ playful appropriations.