This study uses a comparative analysis of the Malayan Emergency, the American experience in Vietnam, and Operation Iraqi Freedom to examine the role and effectiveness of artillery units in complex counterinsurgency environments. Through this analysis, four factors emerge which impact the employment of artillery units: the counterinsurgency effort’s requirement for indirect fires, constraints and limitations on indirect fires, the counterinsurgency effort’s force organization, and the conversion cost of non-standard roles for artillery units. In conclusion, the study offers five broadly descriptive fundamentals for employing artillery units in a counterinsurgency environment: invest in tactical leadership, exploit lessons learned, support the operational approach and strategic framework, maintain a pragmatic fire support capability, and minimize collateral damage. Finally, the study examines the role of education for leaders in a counterinsurgency, and it’s influence on these imperative fundamentals.