This article is an attempt to interrogate some of the predominant forms of analogical reasoning within current cyber-security discourse, with a view to clarifying their unstated premises, major strengths and, vitally, points of conceptual failure. It seeks to improve dialogue between and across the various epistemic communities involved with cyber-security policy. As we seek to adapt to the new security realities of the information age, it is incumbent upon scholars and strategists to address the benefits of connectivity, in all its dimensions, as much as the threats it presents. Current cyber-security discourse channels us into a winner-takes-all modality that is neither desirable nor necessary in the current strategic reality.