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In the 21st century, cyber operations have become the modern manifestation of political warfare between great powers. Many states have made considerable efforts to build up their respective cyber commands. Contrary, or as a complement to this, some states choses to rely upon actors detached from the state for conducting their operations online. What incentives explain this strategy? There are inherent risks with employing proxies and states nowadays have an ability to conduct cyber operations from central military commands. This presents a puzzle. By using a comparative case study approach, this thesis provides a portrait of how two leading cyber actors, Russia and The United States employ different strategies in the digital domain. To understand the motivations behind state delegation of cyber conflict, this thesis applies Principal-Agent theory to explain the relationships states cultivate with non-state actors. I propose a framework containing three hypotheses that ought to affect the decision to delegate; cyber proxies offer states a possibility to enhance their capabilities, save cost and evade accountability. Through analysing the cases, I find that the use of cyber proxies could partly be explained by my hypotheses rooted in the PA theory. Lower internal cyber capability and the desire to save costs may explain why states choses to use proxies in the digital domain. However, the empirical evidence is not strong enough to suggest that cyber proxies offer states a possibility to evade accountability. Rather, it is the cyber domain itself that complicates attribution efforts. Consequently, the findings do not confirm the hypothesis that cyber proxies provide enhanced plausible deniability benefits compared to government agents. In spite of that, this thesis concludes that cyber proxies together with their implications for escalatory dynamics will probably remain challenging in the foreseeable future.