The nature of the hyper-connected, media-saturated, and socially-networked international stage requires that strategic leaders be more attuned than ever to the risk posed by individual actors within their commands, agencies, and organizations. Individual actors – “strategic knuckleheads” – whose incompetence, irresponsibility, bad acts, or culturally insensitive symbols or gestures pose strategic liability to leaders which must be managed constantly, assiduously, and sensitively. Strategic leaders are saddled with responsibility for these individual acts which take on disproportionate importance and significance in the fully-networked world – unfavorable incidents committed by “friendlies” which a generation ago could be managed effectively now often pose an instant and immediate strategic crisis. Acts which once were contained to a specific locale now generate ripples 10,000 miles away in a matter of minutes. The challenge of the strategic leader now, more than ever, is to adopt appropriate mindsets, recognize vulnerabilities, anticipate problems, plan to mitigate bad effects, and react with increased political and operational sensitivity and sensibility when the inauspicious acts of “strategic knuckleheads” inevitably do occur.