This paper will attempt to evaluate the impact and success of the counterterrorism measures initiated by Singapore against the preeminent threat of terrorism to its homeland security. The establishment of the RRG is a step in the right direction and reflects the maturity and foresight in understanding and mitigating the threat to terrorism. Obstacles that need to be addressed however include the broad aims of the state in its attempts to address this complex threat, the difficulty in measuring success and the limitations of counterterrorism measures initiated. While some obstacles are easier to overcome, there remains an overarching sense that there are necessary limitations that any state will have to endure in the fight against a dynamic enemy – even Singapore. Singapore has managed to put into motion one of the most rigorous counterterrorism efforts in SEA, but much of the success achieved has the seeds in the decisive and continuous efforts undertaken by the Singapore government to mitigate the constantly changing and dynamic security environment with strategic measures to counteract these potentially devastating scenarios.