Sojourner Truth’s speech has become famous for its guiding question: ‘Ain’t I a woman?’. Should this be understood as a rhetorical question that has a clear and straightforward affirmative answer? And if so, does the question presume ‘woman’ as a given and stable category, into which Sojourner Truth – and with her, other marginalized women – are to be simply included? This chapter performs a feminist genealogy of the category of women by way of a genealogy of the question ‘Ain’t I a Woman?’. In broad strokes, this chapter traces a trajectory from a black feminist reclaiming of the question, through a poststructuralist feminist rewriting of the question, to a trans feminist resignifying of the question. The chapter teases out how two key dimensions of thinking woman critically interrogating and critically affirm the category ‘woman’ – are at work, in different configurations and degrees, within the different feminist ‘answers’ to the question. Rather than seeing the moves of critically interrogating and critically interrogating the category of woman moves as mutually exclusive, I argue that it is exactly by holding together these two threads, that a dynamic and intersectional understanding of ‘woman’ can be developed which is productive for feminist thought and politics today.