Sri Lanka, one of the most strategic islands in the Indian Ocean, is mired in several domestic political, security and strategic challenges since the end of the armed ethnic conflict in May 2009. However, with the defeat of the Liberation Tigers of Tamil Eelam (LTTE), and the post-war economic boom, it was largely believed that no one would shed tears anymore in the teardrop island. Such hopes and expectations were belied when the country witnessed multiple terror attacks in different locations in Colombo on 21 April 2019. After the attack, people in the higher echelons of the security apparatus and security experts/analysts stated that they had forecast possible threats from the Islamic extremist groups. Why then could the carnage of Easter Sunday not be prevented?