In 1823, Bessy Chambers filed a complaint in the St. George’s slave court in Jamaica. Chambers, along with twenty-four unnamed enslaved people from the New Layton estate, charged that the overseer had forced her to work despite her pregnancy, causing her to miscarry. While her story contests notions of a benign system of slavery in its twilight years, the multidimensionality of Chambers’ gendered freedom claims also disputed the limiting vision of abolition reform for the enslaved, and for women in particular. Chambers and other enslaved women who had a long history of engaging in distinctly gendered struggles against slavery refused to accept the new subordinate roles abolitionist envisioned for them, although they could not always escape its oppressive reach. In going to court, Chambers revealed a right to self-determination as essential to her conceptualization of womanhood. Her pursuit of legal personhood must therefore be viewed as a dual fight against slavery and the restricted freedom abolitionists proposed.