Summary: Madras was the ultimate example of the Raiyatwari system, the involution of the system began with the attempt to establish a landlord Permanent Settlement. The village Settlements in Madras were born out of the distinctive administrative endeavors of the past. The situation changed with the increase in war and authoritative decisions, marking a halt in the initial Settlement approaches. Fortune was more favorable to the ‘dry’ land villages which were grouped based on essential operational factors such as climate, topography, and accessibility. Formulating lucrative revenue structures was fundamentally important in the initial days of British intervention to stabilize the fiscal domain. The settlement intricacies in the varied terrains of Madras including the Madras village Settlements have showcased the complexities and sequential evolution of the land revenue administrative systems.