This thesis employs a material culture lens to examine the finger rings carved by Confederate prisoners and worn and sold by female civilians within the North. It centers on Elizabeth Church Robb, one of the many elite white women who, under the guise of humanitarianism, banded together to supply rebel prisoners, raise funds for the Confederate cause, and even help soldiers escape and return south to fight. Through the carved rings, preserved prisoner-of-war correspondence, and partisan newspaper accounts, we discover pockets of outright Confederate resistance—and even treason—north of the Mason-Dixon Line. The expansive sale and display of jewelry from Union prisons makes a compelling case for why the “Confederacy” needs to be understood as a political entity rather than a geographical one, as well as the prevalence and importance of women in the North who acted upon their own volition in supporting the Confederate cause to keep millions of African Americans in bondage.