The focal point of a war in Afghanistan is dominated by Taliban in the last 17 years. Terrorist Organizations like Al Qaeda or Islamic State (IS/ISIS) have traditionally not been considered as powerful adversaries as compared to Taliban. Yet, policy of making a clear distinction between Taliban and Terrorist Organizations has not paid well. For US, the cost of having been at an extensive war for more than 17 years is huge and it is taking a substantial toll. With resources dwindling, influence declining; the war on terror is on the verge of a major catastrophe. On the other side, the unflinching resilience of the forces of Taliban and Islamists has proved to be just imperishable. The attack of 9/11 compelled US to invade Afghanistan. Compelling USA to fight in Afghanistan has proved to be one of the greatest stratagems. With the war in Afghanistan, the scourge of terrorism has spread like never before in the modern times. The riddle of Afghanistan thus poses a few critical questions. The most important question of all is - Can there be a clear distinction established between Taliban and terrorist organizations like ISIS?