This chapter traces how formerly enslaved Black men and women partook in a legal culture of freedom papers in the sixteenth-century Spanish empire. After enduring lifetimes of enslavement and precarious and lengthy routes to obtain their precious liberty, formerly enslaved Black people often took careful measures to document and protect their hard-won freedom by engaging in the paper-based bureaucracy that underpinned the central tenets of power and justice in the Spanish empire. This often involved investing in the services of notaries to duplicate freedom papers or requesting that various royal and ecclesiastical authorities issue confirmatory paperwork to document their freedom. Their participation in this legal culture of freedom papers reveals how people from the lowest socioeconomic echelons of colonial society measured and valued paperwork – even if they could not read or write – and invested resources to produce and safeguard an array of legal documents to protect their status.