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In the mid-2000s, the operator of New York City’s mass transit network committed more than a half-billion dollars to military contractor Lockheed Martin for a security technology capable, in part, of inferring threats based on analysis of data streams, of developing response strategies, and taking automated action toward alerts and calamities in light of evolving circumstances. The project was a failure. This chapter explores the conceptualization and development of this technology – rooted in cybernetics – and compares its conceptual underpinnings with some situated problems of awareness, communication, coordination, and action in emergencies as they unfold in one of the busiest transport systems in the world, the New York subway. The author shows how the technology, with all the theatrical trappings of a “legitimate” security solution, was apparently conceived without a grounded understanding of actual use-cases, and the degree to which the complex interactions which give rise to subway emergency can be anticipated in – and therefore managed through – a technological system. As a case-study, the chapter illustrates the pitfalls of deploying technology against problems which are not well-defined in the first place, to the neglect of investments against much more fundamental problems – such as inadequate communication systems, and unstable relationships with emergency response agencies – which might offer guaranteed benefits, and indeed lay a firm groundwork for future deployment of more ambitious technology.