The US military’s culture, structure, and process for providing advice to the president and his national security decision-making team are flawed due to the marginalization of unconventional warfare (UW) expertise -- UW is the military’s doctrinal term for support to resistance activities and movements. This marginalization results in inadequate consideration for applying UW as a strategic option for the nation. Through a qualitative methods case study analysis utilizing macro- and micro-level process-tracing with a conceptual framework based on Niklas Luhmann’s Systems Theory, the author shows that viable and acceptable resistance elements existed in Syria in March 2011 to June 2014 and that the conventional US military failed to recognize this development, adequately analyze its implications, and craft a strategic UW option for the national security decision-makers to consider. This finding is significant in that it exposes a deficiency in the US military’s culture, structure and process that results in an incomplete and insufficient menu of military options for the president. If these cultural, structural, and procedural flaws are left unaddressed, the US is likely to repeat this strategic error in the future. The author identifies specific recommendations for national security practitioners; however, the overarching theme is the need to change the institutional culture and the old structures of the conventional military to be able to provide the president a more complete, comprehensive, and creative menu of options to consider when assessing and responding to violent political crises short of conventional war.