International political autonomy, military security, and economic development are the prominent concerns and interests of states in the international system. However, for small states it is difficult to simultaneously maintain these three interests at a preferred level in the international system, particularly when faced with great powers. Although a clear trade-off between security and autonomy exists in allying relationships between a small state and a great power, this situation is not necessarily irreversible for small states. The autonomy–security trade-off could hinge on the anticipated development trajectory of small states and competition between great powers. Pursuing liberal capitalist economic development encourages cooperation and generates peace among small states. Competition between great powers for dominance in the power transition system allows small states to obtain greater international political and strategic autonomy, which subsequently helps small states acquire their economic and security interests. When these two developments come together, small states have an opportunity to reinforce their security, autonomy, and development at the same time.