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When considering covert actions, state leaders face a tradeoff between acquiring maximal information and maintaining secrecy. On one hand, they typically prefer to be fully informed when navigating strategic interactions and military conflict. On the other, a thorough information search requires alerting numerous individuals and organizations of the plan, thereby increasing the risk of a breach of operational secrecy. How leaders adjudicate between the competing pressures hinges on several international and domestic factors. Salient international factors include the value of additional information for assessing the operation’s prospects and the importance of secrecy to the operation’s success and global diplomatic responses. Domestic factors include the distribution of expertise across state bureaucracies, the increased probability of a leak associated with notifying additional personnel, and the political consequences to the leader of disclosure. Planning preceding the Bay of Pigs operation illuminates the central tradeoff while demonstrating the importance of several factors affecting leaders’ choices. The paper sheds new light on links between information and conflict while bringing domestic constraints to the fore.