This Letort Paper analyzes the drivers of assertive military action by Russia, as exemplified by interventions in Ukraine and Syria. It identifies key turning points in Russia's perception of external threat, and the roots of Russian responses to this threat making use of a capacity for military, political, and diplomatic leverage that has been greatly enhanced in the current decade. Color revolutions, the Arab Spring, and Western intervention in Libya are all highlighted as key influencers leading to a Russian assessment that the developments in Ukraine and Syria presented direct security challenges to Russia, which needed to be addressed through direct action. This Letort Paper concludes with a range of policy recommendations intended to mitigate the risk of confrontation with Russia through an imperfect understanding of Russian security perspectives.