ABSTRACT The U.S. Government’s decision to establish a Train and Equip (T&E) Program for Moderate Syrian Opposition (MSO) forces to fight the ISIS terrorist organization came to fruition in the third year of the Syrian Civil War. This article examines the Train and Equip Program, a small but important chapter in the overall post – Sadaam and post Arab Spring societal upheaval in the Middle East. The analysis employs a broad tool-kit that includes: three hypotheses, the multi-causal model for conflict analysis, theoretical grounding in both Groupthink and Lay-epistemics, and an interpretivist lens provided by critical hermeneutics. The aim is to use this discrete unconventional warfare campaign as a platform activity to examine how decision-making and actions at the executive levels of government influenced the overall outcome. The findings of this examination will show that the greatest outcome of the Syria Train and Equip Program may be to serve as a cautionary tale and a guide for policy makers – especially when considering Unconventional Warfare as a policy option.