It would not be an exaggeration to state that Kashmir is at the cusp of deep and profound uncertainty. This uncertainty owes to the nature, form, permutations and combinations and, last but not the least, the duration of the conflict in and over Kashmir. But, it has grown deeper and more intense over time because the default reflex of powers that be has been to merely contain and manage the conflict and its various dimensions. Inherent to and in this approach is the instrumentalization and utility of power to “deal” with the conflict and its various and varied manifestations. But, even a cursory reading of history, broadly speaking, and, particular, the history of conflicts suggests that this particular method of conflict management and containment is a recipe for prolongation of conflict(s). While prolongation of conflicts might create an ambiance and environment of maintaining of a patina of “normalcy”( in relative terms), but it does not lead to peace or, more accurately, comprehensive peace. These general observations apply to Kashmir and the conflict thereof. It would be accurate to state that Kashmir is not defined by peace, defined here as absence of conflict and violence. The people of Kashmir, in particular, caught in the crucible of conflict, the South Asian region and the peoples constituting its firmament, need peace. This condition of peace can only descend upon Kashmir, its people and South Asia , at large, when the conflict in Kashmir is resolved. While the conflict, which among other things, accrues and stems from competing sovereigntisms, and competing ideologies, has over time assumed dimensions of complexity, but it , in the main, does not defy resolution. What is needed is what has till now been a critically missing element in the overall dynamic, that is, political will and determination to actually grasp the nettle and resolve the conflict in all its dimensions. This assumes significance in the larger context of the world and its political trajectory , which is also defined by deep uncertainty. In this melee and maelstrom of deep uncertainty-global, regional and local- prudence and wisdom warrants that a far sighted conflict resolution paradigm be , first conceived and then developed and crystallized so that peace within and without is given a chance. The real test of prudent statecraft is the creation of conditions of peace; not conflict. This is the challenge that powers that be should take on. The first step toward this would be shattering assumptions and world views that beget and prolong the conflict.