Research has demonstrated that teacher allies are integral to social justice work that strives to ensure safety and success for lesbian, gay, bisexual, transgender, queer, intersex, asexual, and other gender and sexuality non-conforming (LGBTQIA+) students. However, prevailing discussions present allyhood in ways that ignore the complexities and contradictions that shape an ally's efforts and experiences. Drawing on narrative-based interviews with 'Bailey,' and integrating conceptual frameworks that seek to make doubt and failure productive, this paper seeks to redefine ally activism in ways that challenge prevailing notions of ally work and that more fully consider sociocultural and political contexts.