Enslaved people sought freedom by any means possible. Most often they achieved free status through hard work, financial accumulation, negotiation, and legal confrontation. Building on slaves’ initiatives, Chapter Two looks at two legal areas in which Cuba diverged from Virginia and Louisiana: manumission and interracial marriage. Although seventeenth-century Virginians set no restrictions on the ability of a person of color to become free, or to marry a white person, that began to change toward the end of the century. By the early eighteenth century, manumission and interracial sex and marriage were restricted in both Virginia and Louisiana, unlike Cuba, where manumission never faced a serious legal challenge. Slaveholders and local authorities in Cuba resented the existence and social assertiveness of free blacks but were constrained by a deep-rooted legal order in which manumission was firmly entrenched and not tied to racial concerns. In Virginia and Louisiana, however, manumission became tied to the development of legal racial regimes that linked freedom to whiteness. In Cuba, black freedom became a contested but integral part of colonial society.