This paper reflects on a research-creation project that investigates the ways in which surveillance is experienced by youth as an embodiment that might be difficult to articulate in words but rather expressed affectively, through emotion and social practice. Our argument is that the aesthetic intervention provoked by research-creation can instantiate encounters that capture surveillance as an ineffable experience of everyday life. We situate our methodological claims in a concrete case study that considers youth engagement with a commissioned contemporary art project. Drawing on the writings of child and youth psychoanalyst W. D. Winnicott, we theorize the importance of a facilitating environment to create the conditions for young people to freely and playfully express meanings they make in their encounters with art. Research-creation suggests a perspective of resistance and failure as productive and constitutive of the possibilities of coming to know, both for the research subjects and ultimately for the authors in their orientation to research inquiry.