“The people are stubborn,” warned Milosav Zdravković, a local official in Ottoman Serbia in 1822. “They do not listen to the orders from the authorities. They are not afraid.” His immediate concern was that the Christian peasants were not paying their taxes to the Ottoman landowners, as required by law. But their refusal reflected a far bigger problem in the breakdown of authority at all levels of society during insurgency and the revolutionary era. Ecclesiastical and communal justice systems were challenged, and it was often unclear who was responsible for overseeing marriage and divorce. Village elders retained certain legal rights, but had no enforcement mechanisms. Indeed, entire systems of vassalage, elder councils, monastic justice, and janissary power were being challenged and replaced by new types of governing and legal bodies. People living in Ottoman Serbia understood things were in flux. They also understood that different forms of legal authority existed. Drawing upon a range of Serbian-language court cases from this chaotic moment, this paper explores how people maneuvered within this tumultuous legal landscape and improvised law in order to claim agency over their lives and define the system in which they lived. Examples include slaves who ran away from Ottoman owners and tested the jurisdictional boundaries of Ottoman law; wives who demanded divorces against the wishes of town elders and local priests; a monk who burned Christian farmers’ fields in protest of new civil property laws, insisting he belonged to the domain of ecclesiastical authority. Bringing together these diverse cases, the paper illuminates how people were developing legal knowledge, encountering and testing the law, and shaping conversations about legal norms and the boundaries of political authority in an insurgency province.