Jammu and Kashmir, no stranger to volatility, especially of the political variety and sort, appears to have entered another phase of intense fluidity. Cutting across and permeating all political spectrums of the region, the nature and denouement of this volatility cannot be foretold. But, it would appear that the practical effects of this might not be too sanguine. Te restate and iterate the obvious, Jammu and Kashmir is then on the cusp of deep and radical uncertainty induced by political volatility and its corollaries. One outstanding feature of uncertainty, generally speaking, is that it, unless, directed towards salubrious and prudent ends, operates under a dynamic of its own and drifts accordingly. Moreover, it is also not amenable to engineering. If this general hypothesis holds and if Kashmir is under the grips of deep and intense uncertainty, then under the absence of guiding mechanisms to drive this uncertainty to prudent ends, then things appear to look ominous in the region. Does this mean all portends gloom and doom here? Not necessarily. There could be options available that redound to the benefit of all. Key to this condition is that variables must be disavowed in favor of constants followed by working on these. To iterate another cliché, Kashmir is at a very delicate phase of its convoluted history. In other words, it is on the fine edge of an inflection point. If the nature of this inflection point is not grasped in its entirety, then there might accrue and ensue conditions which would not be salubrious for anybody. Key to grasping the nature of this inflection point is to take lessons from history, both generically and specifically. History, again generally speaking, is a cruel task master if not understood or not appreciated. But, the beauty of this genre, discipline or domain of knowledge is that it lends itself to scrutiny and hence learning from it. (Indubitably, much of history is interpretation but this does not mean that sober, sobering and prudent lessons cannot be learnt from it). It then behooves all to delve into the depths of history, again both general and the particular, to cull out and glean lessons from it and apply these for the general good. If, however, history is ignored and preference accorded to short term horizons and cycles, then as Santayana famously stated, “those who do not learn from history are condemned to repeat it” will have a resonance here.