Between the 1991 Gulf War and the U.S.-led invasion in 2003, the Iraqi regime faced a cheater's dilemma: how much should it reveal of Iraq's weapons of mass destruction (WMD) capabilities when each additional revelation made it less likely that the country would be rewarded, while continued denial also prevented the lifting of sanctions. The Iraqi leadership struggled to resolve this dilemma, as elites pursued competing policies and subordinates did not consistently obey Saddam Hussein's orders. These difficulties reflected principal-agent problems that were aggravated by the leadership's initial attempts to deny and cover up Iraq's WMD capabilities. Together, the cheater's dilemma and principal-agent problems explain a range of puzzling Iraqi behaviors that came across as calculated ambiguity to the outside world. These findings offer insights into the incentives and constraints that shape how other authoritarian regimes respond to external pressures to eliminate their WMD, and the extent to which they are willing and able to disclose information about past programs and their past efforts to conceal this information from the outside world.