Jane Webb was a free, mixed-race woman in colonial Virginia who sued her husband’s enslaver when he refused to live up to the terms of a contract that would have freed her husband and the bound Webb children. Webb was born in Northampton County on the Eastern Shore of Virginia around 1682 to an English indentured servant and an enslaved Black man and was bound into service for the first eighteen years of her life. She was freed from service around 1700. In 1703, she married an enslaved man named Left. To establish the legality of her marriage and ensure the freedom of any children born into it, Webb entered into a contract with Left’s enslaver, Thomas Savage. She indentured herself to Savage for seven years and any children born into the marriage through 1711 for eighteen years. After 1711, Left would be freed, and any children born to the couple thereafter would bear no obligation to Savage. When Savage subsequently refused to free Left and successively bound all of Webb’s children to his service, Webb turned to the courts to gain her family’s freedom. In multiple appearances at the local court, Webb displayed a sharp legal consciousness and deployed an array of legal strategies, eventually suing Savage for his failure to live up to the terms of the contract. While she was ultimately unsuccessful in freeing Left, and her children were bound to service until adulthood, her children did eventually live as free Blacks. Webb’s use of her legal expertise was part of a more widespread effort by free Blacks in early Virginia to protect their increasingly fragile rights.