The author, as a UN Commander in Bosnia in the early 1990s, faced what he believed to be an ethically insoluble dilemma entangled in the Wicked Problem of Bosnia’s civil war. Bosnia’s civil war was a Wicked Problem constructed by history, the warring factions and the UN’s policy of neutrality. The moral uncertainty of leading in Bosnia’s Wicked Problem generated a tendency to construct Tame Problems enabling forthright action guided by deontological principles of moral certainty. The reality of the Wicked Problem required leaders to adopt Utilitarian judgements based on projected consequences, as in Bosnia’s grey zone the Deontological certainties did not appear valid. When a Wicked Problem morphed into a crisis or Critical Problem requiring direct action, the morally correct course had to be instinctive aligning with Virtue ethics, the ethical character of the actors. This article is an attempt at reflective learning through post hoc sense making of events portrayed in a case study, the events fractured relationships, changed lives and provided stark lessons.