Elements of counterterrorist strategy, and the Global War on Terror that has defined it in the wake of September 11, 2001, are discussed in terms of four dilemmas. A key feature of a dilemma is that it presents a problem, or decision situation, which is not resolvable without significant side effects or unintended consequences. Recognizing and addressing these side effects and consequences is key to practices of understanding and learning from experience and of reformulating strategy in response to changing operational environments. Four key dilemmas are identified and briefly discussed: The labeling of groups as terrorist; the priority accorded to force protection within military doctrine; the emphasis on freedom and democracy as a justification for both military and humanitarian intervention; and the extent and duration of the political commitment to engage in a campaign against terrorism on a global basis. Costs and consequences of recent responses to these dilemmas within counterterrorist strategy, and particularly within Iraq and Afghanistan, are briefly highlighted before a discussion of some of the possibilities and risks arising from the conjunction of the ‘Arab Spring’ of 2011 and the death of Osama Bin Laden. The medium and long term outcomes of both these developments are highly uncertain, but present an opportunity to rethink, and reorient, key elements of counterterrorism strategy. Incorporating dilemmas such as those addressed within the evaluation of new strategic directions will help to formulate an understanding of potential costs as well as benefits more clearly than may have been the case in the past.