The humiliating and chaotic US withdrawal from Afghanistan on August 30, 2021, preceded by a swift collapse of the Western-backed government in Kabul two weeks prior, brought the curtains down on the two-decade-long US-led military intervention. Startlingly the Taliban swiftly eclipsed Afghanistan’s political and military landscape, triumphantly proclaiming an end to war. The rise, fall, and the rise of the Taliban over the last two decades have been closely intertwined with the changing regional dynamics. This chapter etches out what underpins the changing political alignments and re-alignments in the region particularly in light of Beijing, Moscow, and Tehran finding a congruence of interests with the Taliban and Rawalpindi. It will be argued that growing friction with Washington coupled with the rise of Daesh projected as the seminal security and ideological challenge led these actors to embrace and repackage the Taliban as grassroots liberators who ended the foreign occupation. The Taliban too embraced these actors in a bid to accumulate diplomatic and political leverage and shore up prospects for garnering legitimacy. Noteworthy in this context are the contradictions that underpin this mutual embrace given how uneasily the Taliban’s worldview sits with the domestic politics of these players.