After successive episodes of Russian aggression, both Estonia and the North Atlantic Treaty Organization (NATO) remain on edge about the future of their relationship with Moscow. To understand how Estonia has deterred Russia from further hostile acts, this paper analyzes the Estonian government’s response to them and how the establishment of defense programs have made Estonia a pillar of anti-Russian policy in Europe. Such programs and policy changes which continue to deter Russia from these aggressive tactics include but are not limited to NATO’s Cooperative Cyber Defense Center of Excellence, the EU’s East StratCom Task Force, and the development of dependable relationships between NATO, the EU, and the Estonian private defense sector. The paper also analyzes the overall successes and deficiencies of these policy changes, makes future recommendations for the Estonian government, and evaluates the implications of these changes in the broad realm of international security. Analyzing these successes and deficiencies is important for determining the overall effectiveness of the changes in Estonian policy over the past decade. Through in-person interviews with both American and Estonian government officials, online research, and interactions with academic experts on the subject, the paper argues these new programs and evolving relationships are an adequate and effective deterrent to prevent further Russian cyber and conventional military attacks.