This article focuses on an out-of-school youth participatory action research project to better understand both how schooling emerged and was challenged in a liberatory space. This project explores the entanglement of schooling, learning, and youth in a youth participatory action research (YPAR) setting. There were six youth and one academic researcher involved in the project which spanned two years, 2018-2020. This work was driven by the research questions: if schooling is a non-human agent, how does schooling manifest in an afterschool YPAR space, and how, if at all, was schooling interrupted/challenged? This project utilized ethnographic methods, interviews, cognitive maps, and posthumanist theorizing to explore the entanglements of human, nonhuman, and discursive agents. Findings illustrated that within the afterschool space, the participants were constantly in tension of holding to and pushing against those agents buttressing schooling -- hierarchical relationships, adultism, prescriptive entanglements, and internally disciplining and surveilling themselves. When it came to the learning lines of flight that emerged within the YPAR space, participants created community by making and holding space for one another. The group rejected linearity and embraced the unpredictability of learning. By centering democratic collaboration, youth knowledge/experiences, and learning, the collective demonstrated how YPAR can be a tool of resistance to the dominating forces of agential schooling.