This article seeks to provide an explanation of the shifts and trends in the insurgency and Russian counter-insurgency strategy in the North Caucasus. The first section identifies the multiple factors which initially contributed to the radicalisation and Islamisation of the conflict in Chechnya and how this fostered increased instability in the North Caucasus by the late 1990s, representing a serious threat to the security and integrity of the Russian state. The second section sets out how the incoming prime minister and then president Vladimir Putin seized on the growing crisis in the North Caucasus to develop and refine a new strategy which not only gained the support of the general Russian public, but also was a critical factor in cementing his personal popularity. The strategy also had some notable successes, not least in the relative pacification of Chechnya and the start of the reconstruction of the war-damaged republic. However, the strategy also had its less successful and more negative consequences, which have revived and changed the nature of the insurgency towards a more Islamist and diffuse character and presented new challenges for Russia’s counter-insurgency strategy. The final section makes a division between the social, economic and political factors and the religious and ideological factors which are driving the insurgency and argues that greater weight should be accorded to the religious and ideological factors than often accorded by analysts.