South Asia’s strategic stability is embroiled with deep rooted trust deficit, technological arms race, sub-conventional war trends and evolving doctrines. In the absence of sustainable dialogue process, the strategic anxieties of both India and Pakistan have consolidated into aggressive force postures leaving little room for shared learning. Instead of forging grounds to seek resolution to the bilateral disputes (complex learning), both states have adapted new means to pursue their existing state policies (simple learning). The drivers of nuclear learning in South Asia are primarily assessed at three levels of analyses i.e. individual, organizational level which directly affects the third tier i.e. the state level. Over the years, the state institutions in two countries have evolved following parochial interests eventually giving birth to rigid organizational cultures. Moreover, the idiosyncratic role of key decision makers remained vital in determining the military crises in both pre and post-1998 eras. Each military crisis is different in its backdrop, occurrence and termination from its preceding event. The reason being, each military crisis taught different lessons to either state, subject to different interpretations drawn by the decision makers on both sides. Hence, unlearning at the individual level is responsible for shaping a peculiar strategic culture of South Asia promoting crisis instability. It is important to explore the factors determining crisis behavior in the region while the two states have operationalized their deterrent capabilities and pursuing assured second strike pathways. Ideally, the acquisition of nuclear weapons should have inculcated enough confidence in both states to transform their ‘enduring rivalry’into a new relationship having greater credence on nuclear deterrence. In reality, both states have used nuclear shield to pursue their existing state practices thus, complicating deterrence stability in the region (stability- instability paradox).The study analyses the lag in nuclear learning as a determinant of crisis instability. One of the key levels of analysis is the individual level reiterating the role of strong personalities operating at different tiers of decision making remained involved in crises eruption. Interestingly, the ‘culture of secrecy’that shrouded in the development of nuclear programs of both the countries is eventually found a key factor for confining the nuclear decision making circle. This explains the inconsistent policies and risk prone behavior as a direct outcome of nuclear unlearning by the state due to incompetent judgment of the individuals facing security paranoia and organizational pathologies in the concerned bureaucracies. The recurrence of military crises is explained through the prism of nuclear learning, constructivism and cognitive dissonance in shaping a strategic culture conducive for crisis instability.