This article examines legal relations between estate owners and their servants and workers on Danish estates in the nineteenth century. From the end of the eighteenth century onwards, the traditional privileged role of Danish estate owners was changing, and their special legal status as “heads of household” over the entire population on their estates was slowly being undermined. The article investigates the relationship between estate owners and their servants and workers in legislation and court cases during these times of change. It examines the Danish servant acts from 1791 and 1854 and identifies the asymmetric order of subordination and superiority in this legislation. The core of the relationship was still a “contractual submission” that, to some extent, was private and unregulated by law, and estate owners were entitled to impose sanctions and physical punishment on their servants and workers according to their own judgement. When the Servant Law of 1854 abolished estate owners’ right to punish adult servants physically, it was a significant break from the old legal order. However, a central element in the legislation, before and after 1854, was that servants’ and workers’ disobedience towards estate owners was illegal. By analysing court cases, the article examines the borderlands of the legal definition of disobedience. The elasticity in the legal system was substantial – and frequently favoured the owners. In the legal system, the notion of disobedience served to protect the last remnants of the traditional legal order of submission and superiority.