This chapter identifies and analyses security challenges posed by Russian para-statal military organisations (PSMOs) to European security interests. It focuses on three challenges: 1) the challenge of Authoritarian Conflict Management (ACM) abroad; 2) the challenge of enacting ACM and related PSMO limitations; and 3) the challenge of subversion at home. The chapter emphasises international power shifts, increasing authoritarian great power activism, and the seeming limitations of the ‘liberal stance’ towards conflict management that point toward a different approach undertaken through Russian PSMOs. Assessed together, the potency of Russian PSMOs rests in offering an alternative to European engagement, the heightening of violence overseas and its repercussions, and the fear of changed PSMO effort on the European continent.