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In 2001, following the Taliban’s ousting from Afghanistan, the United States signed the Bonn Agreement directly with an Afghan delegation. Nineteen years later, in a bid to end the longest war in American history, the Trump administration signed the “Agreement for Bringing Peace to Afghanistan” with the Taliban, this time circumventing any direct involvement from the Afghan government. Is the US-Taliban deal a major diplomatic solution to a protracted conflict that signifies the importance of diplomatic solutions to military action? Or is it a war-failed and diplomacy-bound-to-fail scenario? This paper analyzes the issues and challenges facing the peace process in Afghanistan, with a focus on the diplomatic efforts by the United States.