The operational and doctrinal relevance of Kautilya’s Arthashastra and Clausewitz’s On War in today’s counterinsurgency operations remains firm and valid. In numerous instances, they provide us a template to analyze various aspects of a counter-insurgency operation including the use of local values and principles as a tool to understand the strategic culture of an adversary. It must be understood that the evolution of technology may improve one or other aspects of a counterinsurgency operation, but the core elements remain more or less the same and are diverse depending upon the region of conflict. The non-linearity and flexibility of an insurgency are such that it can exploit various means such as misinformation campaigns, religious and ideological differences, as well as enlisting foreign support to keep it alive during the conflict.