The Taliban 2.0 have made overtures to states across different regions to seek international recognition. In a departure from their past isolationist foreign policy practices, I argue the Taliban have expediently, yet uncharacteristically, pursued these initiatives in a spirit of “ pragmatism.” The modus vivendi they have reached with Iran demonstrates the Taliban’s unprecedented prioritization of pragmatism over ideology. I draw upon Machiavellian pragmatism in International Relations theory to examine the shift in the Taliban’s political posture through the lens of Iran–Afghanistan relations in three crucial episodes: the Taliban’s rule over Afghanistan from 1996 to 2001, the post-9/11 Afghanistan, and the resurgence of the Taliban since August 2021.