From the seventeenth century through the beginning of the Civil War, the United States had the largest population of enslaved children in the world. A product of natural increase and matrilineal laws, these children endured a unique slave experience that cultivated the essence of slave culture. With the growing value of child slaves at the turn of the nineteenth century, many masters advertised the escape of their slaves in local newspapers, offering rewards for their hasty returns. Keeping in mind that these advertisements are a reflection of the masters’ perspectives, this thesis analyzes runaway child slave advertisements, arguing that they provide essential insight into the lives of enslaved children by articulating the cultural pertinence of individuality, familial bonds, and gendered labor expectations within the ever-changing institution of American slavery in Virginia from 1760 through 1820. Typically in the hopes of being reunited with family, more than 800 enslaved children attempted to escape Virginia in this era alone. Often escaping shortly after their transition to occupational adulthood, the children mentioned in these advertisements were most often males between the ages of nine and fifteen; however, the growing impact of reproduction in an era of the abolished slave trade created an increase in the number of enslaved girls who escaped. With the expectation of lifelong productive and reproductive labor, enslaved children resisted the constraints of slavery in search of the comfort only freedom and family could provide.