Security is discussed through the four dimensions of external, internal, civil and societal security, and policies are examined in terms of their sustainability for the next 50 years of Singapore’s development. Questions asked include: what demographic constraints underpin the challenge of the Singapore Armed Forces, and what implications does this spell for its future? In light of the threat of domestic terrorism and the need for greater internal vigilance, what measures can we take to balance the protection of individual rights versus the needs of state security? To what extent is judicial corporal punishment justified by simply its deterrent effect as we aspire to become an increasingly humane and civilised society? And in the interests of societal cohesion, what possible policy initiatives might be considered?