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Over the years, the Taliban have overwhelmingly grown in influence and their stature is being well recognized; exerting more pressure on Washington’s future orientation in Afghanistan. Amidst the backdrop of transitions taking place in Afghanistan’s political landscape, the foreseeable future has, ostensibly, rekindled the prospects of peace. Although peace process is gradually moving further, yet both sides are reluctant to compromise on each others’ terms. Since the assumption of power, President Trump’s approach to Afghanistan has been oscillating in consulting varying options to bring the Taliban to their terms rather to indulge, in true spirits, in a widely acknowledged political framework for peace. These chosen policy actions posit more challenges and less opportunities for peace in war-ridden Afghanistan. The emergent scenario requires a comprehensive, well-crafted and compromising structure to be devised, featured with inclusiveness of all stakes and issues involved in this prolonged conflict. Evaluating and analyzing President Trump’s strategic policy toward Afghanistan, this paper aims to explore the manifesting failures and grey areas of Trump’s Afghan strategy and also attempts to provide strategic foresight while considering the framework of endgame in Afghanistan