Does colonialism have long-term effects on political stability? This question is addressed in a study of India’s Naxalite insurgency, a Maoist rebellion characterized by its left-wing proponents as having roots in the colonial period. The article highlights three mechanisms linking colonialism with contemporary Naxalite violence—land inequality, discriminatory policies toward low-caste and tribal groups, and upper-caste-dominated administrative institutions. It analyzes how the degree of British influence relates to Naxalite conflict in 589 districts from 1980 to 2011. A positive association is found between British influence and the strength of the Naxalite rebellion across all of India, within both the “Red Corridor” region and former princely states. The results are robust to a coarsened exact matching analysis and a wide array of robustness checks. The findings call into question whether the supposedly beneficial administrative and institutional legacies of colonialism can be evaluated without reference to their social costs.