Midnapore was one among the first three districts ceded to the East India Company in 1760 by Mir Qasim, the other two being Burdwan and Chittagong. Following this, the acquisition of the diwani of Bengal, Bihar and Orissa in 1765 launched the East India Company into a complex administrative role related to revenue in an alien territory with complex, multi-tiered, customary land rights that were beyond their knowledge. Their attempts at revenue collection and the accompanying imposition of a legal, rational state on a customary framework led to tragedies like the Bengal famine of 1770. It served as the impetus for the initial uprisings against colonial rule, which mainstream accounts on resistances in the early colonial period tend to omit. The study here aims to shed light on the nature of rule transition and complexities regarding land ownership that the Company encountered, the special nature of Midnapore frontier, and phases of the chuar rebellion pre- and post Permanent Settlement. Special attention has been placed on conceptual clarification of chuars, paiks, their status overlaps and subalternity and on analysing the nature of the rebellion in the light of Eric Hobsbawm’s concept of banditry and Ranajit Guha’s analysis on features of peasant insurgency in colonial India.