The Afghan Taliban and Pakistan are often touted as two sides of the same coin, given the latter’s pivotal role in supporting the movement since its emergence in 1994, and subsequently in resurrecting it as a potent insurgent force against NATO. It was believed that this would enable Pakistan to exert considerable influence on events across the Durand Line. However, developments over the last five years belie this claim. Drawing on historical and geopolitical context, this paper argues that Rawalpindi’s motives in supporting the Taliban are deeply embedded in its historical experience and vulnerabilities, as well as being influenced by the actions of other state actors in the region. Drawing on the work of K. J. Holsti, Alvin Rubenstein, and Rafael Birnbaum, the paper argues that, whilst the relationship between Rawalpindi and the Afghan Taliban displays patron–client characteristics, it is difficult to view it as a linear, reductionist relationship.