This chapter looks at the tensions between slavery and freedom in the three slave societies of Cartagena, Antioquia, and Popayán, probing the ways in which specific officials and slaveholders interpreted and used the specter of slave insurrection in light of their own interests and local conflicts. In contrast to the stereotypes of insubordinate slaves, the chapter maps out slaves’ culture of expectation. Underpinned by a dynamic grapevine transmitting rumors and tales, this culture of expectation included notions about the end of slavery and discussions on tactics to improve working conditions or accelerate the coming of freedom. Many enslaved communities told hopeful fables of peaceful liberation and legally recognized emancipation. The rumor that a merciful monarch had decreed collective freedom reappeared periodically. For some, the hope was based on manumission promises by masters. Others thought that God would end slavery and punish the masters. Many slaves hoped that they could become law-abiding members of the body politic (paying taxes, obeying magistrates and priests, and living in their own towns) after emancipation.