Cyber deterrence is not like regular deterrence. In regular deterrence, say between two nuclear powers, the development of more nukes does not make hardened silos less effective on a per unit basis. Cyber deterrence is different. Cyber deterrence is inextricably riddled with tradeoffs and interdependencies that regular deterrence lacks. This chapter outlines the essential tradeoffs between cyber deterrence by denial, punishment, entanglement and taboo. Each case example illustrates how investing heaving in one form of cyber deterrence costs, at margin, in some other category. Cyber deterrence can be optimized, but only with these essential tradeoffs in mind.