Since the U.S.-led coalition initiated military action against the Islamic State (IS) in northern Iraq in August 2014 and in Syria the following month, a number of victories have been achieved. However, progress thus far can best be described as a series of loosely linked tactical gains, rather than a significant strategic advance. The stated coalition objective is to “degrade and destroy” IS as a militant organization, but it remains a potent armed force capable of capturing valuable territory and inflicting considerable material damage on its adversaries. The time has now come for a bold and critical re-evaluation of the current anti IS strategy and the core analytical understandings driving counter-actions. In addition to honestly assessing progress thus far in countering IS, this article highlights three key issues requiring acknowledgment and recommends their inclusion within the foundational thinking of a new and more effective counter-IS strategy.