This PhD dissertation covers approximately a century and a half of Sri Lanka’s history, with a particular focus on the second half of the eighteenth century. At the time, much of the population of this South Asian island lived under the self-proclaimed rule of the Dutch East India Company (VOC). In putting this rule into practice, the VOC relied on a veritable army of clerks, civil servants, and bureaucrats, who registered thousands of indigenous families and their land holdings on behalf of the Company. This registration process aimed to exploit the caste-related labour services of these families and the agricultural products (such as rice) that traditionally had to be ceded to the state. However, the research of this thesis shows that this registration process was by no means a one-sided development. Local people, customs, and infrastructures all had a significant influence on how lives, land, and labour were documented. Moreover, the documents resulting from this process, such as the ‘thombo’ land and population registers, were used on a demonstrably large scale by Sri Lankan families to secure their social status, property, and inheritance – for example, as evidence in court. This allowed local communities to demonstrably appropriate these colonial records, a fact that has received little attention in previous scholarly work.