Around the world, incarcerated trans women experience substantial victimisation and mistreatment equating to increased risk of suffering and self-harm compared to the general incarcerated population. This case study shares the story of Natasha Keating, a trans woman incarcerated in two male settings in Australia between 2000 and 2007. We examine 121 letters of complaint and self-advocacy authored by Natasha and provide an analysis of the discursive strategies Natasha employed to construct an affirming self-identity, and effect social change within a system designed to curtail self-determination. Through an impassioned letter-writing approach leveraging military metaphors, evidence of Natasha’s cognitive transformation is found. The letters showcase the significant implications Natasha’s activism, self-agentism, and self-determination had in naming and seeking to dismantle the systems of oppression that incarcerated trans women experience.