Abstract Why has western foreign policy exhibited a record of sustained strategic failure, from Afghanistan to Ukraine? Why is it that despite the intellectual attention devoted to identifying the foundations of good strategy, outcomes remain so poor? This study pinpoints an inability to relate to problems proportionately as a major factor that accounts for bad strategic results and the growth of an anti-strategic predilection in policy-making. This informs a range of factors extending from a liberal-elite commitment to moral missions that undermine exit strategies and bounded objectives which sets in train an escalatory dynamic that inexorably spirals towards failure. Furthermore, rarely is there any accountability for predictive ineptitude, which merely entrenches the propensity towards poor strategic performance. The argument contends that these factors can all be captured within an enduring paradigm of total war, which exerts an overdetermining influence on western policy-making, pushing the formulation of strategy towards abstract goals and the unrestrained application of resources. While there are no easy answers to overcome these deep-seated problems in western approaches, this article suggests that an attempt to move the idea of strategy away from ‘problem-solving’ to ‘problem-framing’ can offer the prospect of more considered policy reflection and facilitate a process of learning from mistakes rather than repeating them.