In what represents a radical departure from the Kremlin’s past trajectory of branding the Afghan Taliban as a ‘radical’ and ‘terrorist’ group, it has sought to actively engage it well before its formal ascent to power in August 2021. This article will examine the evolving trajectory of the relationship between Moscow and the Afghan Taliban. It will critically engage with both the key factors that have traditionally shaped the Kremlin’s views on the Taliban and what underpins its subsequent pivot to the group? In seeking to critically discern Moscow’s embrace of the Afghan Taliban, this article will draw upon the larger historical and geopolitical context to put into perspective key factors that have shaped the trajectory of Moscow’s engagement with Afghanistan. Herein, it will be argued that Russia’s current engagement with the Taliban is underpinned by pragmatic realism. The changing geopolitical context, as well as the shifting political and military ground within Afghanistan, has animated the transformation of Moscow’s perceptions of the Afghan Taliban from a security threat to being viewed as the principal bulwark against key security threats, particularly the Islamic State Khorasan Province (ISKP), following the chaotic withdrawal of the United States from Afghanistan.