The Gray Zone represents a space between peaceful state rivalries and war. Within this space actors have developed hybrid strategies to extend their influence. This concept of conflict is best illustrated by Russia’s actions in Eastern Ukraine in 2014. Gray Zone doctrine leverages ambiguity to create an environment in which adversaries are unable to make strategic decisions in a timely and confident manner. Cyber Operations, because of the attribution problem, lend themselves to this kind of conflict. This article explores the interactions between the Gray Zone and cyber operations and considers questions which NATO must address in order to adapt.