This chapter explores postwar planning for Iraq using a similar approach to that used in Chapters 1 and 2. Specifically, it addresses how postwar planning for Iraq unfolded from the 1990s through May 2003, how we handled the planning tasks, and finally, why we conducted the planning so poorly. In particular it explores how the unresolved tension between promoting democracy and a rapid withdrawal helped derail the postwar approach. The U.S. did not develop a cohesive strategy to address the underlying trade-offs, so the Iraq planning was at odds with itself. This helped give rise to incompatible goals, a flourishing of governmental infighting, and a general sense of confusion that squandered our key window of opportunity. This chapter illustrates how we might have made smarter choices in Iraq, and probably attained a better outcome.