An important branch in recent debates on the nature of the judiciary in colonial south India has focused on the extent to which the judicial institutions—and the social transformations mediated through them—were controlled by the colonial state. This debate is of interest not only from the point of legal history. From the broader perspective of social and cultural history the debate is important because it draws attention to issues such as indigenous agency, conceptual negotiation and the hybrid nature of institutions under colonial rule. It is these issues I intend to address through an analysis of indigenous litigation in the Mayor's Court in late eighteenth-century Madras. The analysis falls in two parts. First, I analyse how indigenous agents availed themselves of the court, despite an official colonial policy of excluding disputes between Indians from its jurisdiction. In the second part, I focus on the ways in which the nature of property was contested and negotiated in complex dialogues between indigenous litigants and representatives of the colonial judiciary. Both parts of the analysis indicate that important aspects of the litigation in the Mayor's Court were largely beyond the control of the colonial authorities.