This article discusses the nature, opportunities and limitations of small state grand strategy. It identifies the similarities and differences between the grand strategies of small states and great powers and unpacks the nature of traditional defensive small state grand strategies hiding and shelter-seeking as well as more recent offensive, influence-seeking small state grand strategies under the heading of smart state strategy. The article argues that while small state grand strategy remains tied to national security and is formulated in the shadow of great power interests, a changing security environment creates both the need and opportunity for small states to use their weakness instrumentally for maximizing interests. The likelihood of success depends on a pragmatic political culture and the willingness and ability to prioritize goals and means to utilize their nonthreatening small state status in “smart” or “entrepreneurial” policies.