This article draws from my involvement in critical social work education and my position as an aspiring ally of the Mad movement in the Irish context. I use a reflexive auto-critique as a methodology to consider a significant shift in my engagement with Mad matters which has led to new ways of (un)learning critically about madness and distress in education and activism. This is a shift from celebrating criticality and inclusion strategies, and in particular service-user involvement in education, to problematising criticality and its potential to perpetuate power inequalities within mental health and education systems. It is a shift from viewing critical education as a process of knowing about distress and Mad people to a process of knowing with and from Mad people, service-users, and survivors. The emerging field of Mad Studies provides a conceptual framework to inquire about knowledge and knowers, to consider issues of co-option and epistemic injustice, to focus on pedagogies for unlearning, to ask questions about representational politics and the complexities of being an engaged academic and Mad positive ally. Guided by Mad Studies as a mode of analysis, I recognise that inclusion of madness in university curricula can work in ways that continue to pathologise and subjugate Mad people. This is an unsettling recognition that leads to an interrogation of my own praxis as an academic and an aspiring ally of the Mad moment. I propose that prefigurative politics are central in these considerations as genuine engagements with mental health matters need to model the changes we aim to achieve. Engaging with the tensions of inclusion politics, the complexities of madness, and the unsettledness this engagement generates, can be a source of knowing through epistemic humility and a resource for networks of solidarity.