For free black women in the pre-Civil War American South, the status offered by ‘freedom’ was uncertain and malleable. The conceptualization of bondage and freedom as two diametrically opposed conditions therefore fails to make sense of the complexities of life for these women. Instead, notions of enslavement and freedom are better framed as a spectrum. This article develops this idea by exploring two of the ways in which some black women negotiated their status before the law—namely though petitioning for residency or for enslavement. While these petitions are atypical numerically, and often offer tantalizingly scant evidence, when used in conjunction with evidence from the US census, it becomes clear that these women were highly pragmatic. Prioritizing their spousal and broader familial affective relationships above their legal status, they rejected the often theoretical distinction between slavery and liberation. As such, the petitions can be used to reach broader conclusions about the attitudes of women who have left little written testimony.