Chapter 4 examines the obstacles enslaved women faced in escaping bondage in post-Revolutionary America. The case of Elizabeth Freeman, an enslaved Black woman in Massachusetts who sued for her freedom, captures the tenacity of Black women, who not only resisted with their feet, but also used the courts to gain their freedom. By highlighting the case of Ona Judge, the fugitive slave of George and Martha Washington, this chapter brings to the fore successful escapes in which enslaved women overcame formidable obstacles to freedom. During the post-Revolutionary period, Bett and other enslaved women developed several strategies for overcoming obstacles to freedom. As daughters, mothers, and wives, they contested oppression and invented solutions that defied their status as enslaved women.