This article examines the perennial mutual frustration between presidents and their military advisors over decisions to use force. What often appears to be a personality-driven or political debate between the commander in chief and his strong-minded military advisors actually has deeper institutional and cultural roots. The “professional” military officer has certain expectations about how to craft “best military advice” for the president that are deeply embedded into the organizational culture and in fact hard-wired into the institutionalized and incredibly detailed military planning processes. This planning process is designed with expectations about the roles civilian leadership will play in providing guidance, which are in many ways out of synch with the expectations of the president and his civilian advisors. Ultimately, the output of the military's planning process fails to deliver the type of nuanced advice in the form of creative options that the president needs.