Pakistani President Ayub Khan learnt that military escalation is difficult if not impossible to control during the 1965 India-Pakistan War. Ayub Khan and Zulfikar Ali Bhutto developed a strategy to wrest control of Jammu and Kashmir based on four assumptions. First, that Kashmir was ripe for rebellion. Second, that India did not have an appetite for war following her defeat to China in 1962. Third, a military solution to the Kashmir dispute was time bound, as India’s massive military imports would make conventional conflict redundant by the end of the 1960s. Lastly, and perhaps most importantly, Khan betted that Indian retaliation would be controlled because of what he believed to be the United States' and the UK’s inherent interest in a stable South Asia. He was wrong on all four counts. This article underlines why gambling on external support in matters of military adventurism is a dicey strategy at best, and a disaster at worst.