This article discusses slavery and the lives of enslaved people in Jaffna, northern Sri Lanka, under Dutch and British rule. It argues that by sanctioning and tapping into a perceived local practice of slavery and legally constituting slaves, Dutch colonial rulers further strengthened the power of the dominant caste Vellalar over their subordinates. This was done through processes of registration, legal codification, and litigation. For some enslaved people, however, bureaucratization provided grounds for negotiation and resistance, as well as the potential to take control over their individual lives. British rule that took over areas controlled by the Dutch East India Company or Vereenigde Oostindische Compagnie—first in the guise of the East India Company (1796–1802), then under the Crown (1802–1948)—introduced a number of measures, acts, and incentives to dismantle slavery as it was practiced on the island. This article draws from Dutch and early British period petitions, court records, commission reports, and slave registers to interrogate the discourse of freedom that permeated the British abolition of slavery from 1806 to 1844 and suggests that in Jaffna after abolition there remained bondage in freedom.