At the turn of the 19th century, across most regions of Latin America, free people of color outnumbered the enslaved. Even in the Western Hemisphere's last societies to abolish slavery, Cuba and Brazil, the only exceptions to this pattern, the size of the free population of color in some regions increased throughout the 1800s. This demographic sector emerged and expanded primarily through manumission. This article examines recent scholarly attention to freedom litigation which has shown manumission's deep entanglements in custom, unwritten negotiations between enslavers and enslaved. Customary arrangements for manumission took a variety of local forms that courts often recognized even when they misaligned with written law. Custom's privileged status within the Iberian‐Atlantic legal regime and a fragmented local elite that could not control it placed some power in the hands of enslaved people in some areas of Latin America. Moreover, through its orality and embedding in local social relations, custom also offered a low entry point into the justice system for subaltern sectors. In Latin America, the Age of Emancipation was not just a time of conflict over liberalism's potential to free enslaved people. It was also an age of conflict over custom's liberatory capacity, and as such, an age of popular legalism.