Solutions to the countless crises middle schools face are typically proposed by policy makers with little actual classroom experience. Meanwhile, essential insights from students on the issues they experience firsthand every day are largely ignored. Youth participatory action research (YPAR) can help, as social researchers collaborate with youth, training them to identify and research concerns in their schools and take leadership to address them. Yet numerous factors can pose obstacles, including factors related to the youth's developmental capacity to partake in such activity, as well as facilitator factors that can inadvertently cause more harm than good. This article offers a critical investigation of a case of YPAR in a university-middle school partnership at a school identified as in need of turnaround because of an entrenched culture deemed unsafe and not conducive to learning. The analysis of this undertaking answers a call for more transparent descriptions of tensions and contradictions that participants grapple with in such projects, providing potential YPAR facilitators with the insight to identify and prepare for problems long before they derail a project, helping to ensure that efforts do not go to waste or unintentionally cause harm to the communities they are meant to serve.