As settler women, former teachers in First Nation communities, and scholars working in Indigenous education, we are responsible for engaging in the complexities of reconciliation through an allyship framework. In this article, we use duoethnography to critically engage in dialogue around the practice of allyship. In revisiting formative moments in our individual and collective teaching and research journey, we wade through some of the current tensions around solidarity work, problematizing the performative and binary approaches to allyship we see increasingly propagated across academic institutions and social groups. This critical dialogue illuminates how we might rethink becoming stronger collaborators with Indigenous people and engage others in exploring their allyship practice.