As the sun set on Saddam's Iraq, the high hopes for peace, freedom, and democracy evaporated as the Coalition faced an altogether different reality in the post-war environment. Insufficient planning and integration between State and DoD led to uninformed decision-making, reversing the momentum gained by the military success. Paying closer attention to Iraq's relevant history of occupation and repression, its political, social, and military cultures, and the inherent ethno-religious schisms would have revealed the promise of ethnic and sectarian violence in the absence of Ba'athist tyranny and the perils of building democracy in a land devoid of a democratic heritage. In a race to dismantle the institutions of the old guard, many Sunnis willing and able to share in Iraq's rebirth were marginalized or demonized. The CPA's over-reliance on Iraqi exiles in government formation at the expense of resident actors put a Coalition stamp on an unfamiliar Governing Council that harkened back to the British occupation and detracted from its popular support. An overly sanguine strategy to expeditiously transfer sovereignty ignored the adequate troop levels and time line necessary to establish comprehensive security first, grass roots legitimacy next and democratic institutions third, once the political climate was adequately set. Should America embark upon regime change in Tehran, shaping the peace will be every bit as gruesome, but understanding how miscalculations with respect to government, society, and security led to increased violence and instability in Iraq could be instructional in a post-war Iran.