This article seeks to examine through a realist international relations’ lens the geopolitics and the security environment of the South Caucasus, and specifically the security challenges Armenia will face over the next five years. As the South Caucasus is cemented by collective security agreements and the stagnant conflict over Nagorno-Karabakh, the regional dynamic shifts incrementally. Significant historical events, such as the Baku-Tbilisi-Ceyhan pipeline, the April 2016 Karabakh flare-up, and the completion of the Trans-Anatolian Pipeline provide the foundation for a forward leaning analysis. This article addresses three questions. First, considering the changing international order, what is the current security environment in the South Caucasus? Second, what are the geopolitical concerns in the South Caucasus? Third, what are the specific national security challenges for Armenia? It reveals that the South Caucasus security environment is energy focused, changes in the Nagorno-Karabakh conflict are contingent upon energy geopolitics and Russia, and that Russia will continue to hinder Armenia’s growth and independence, thus challenging Armenia’s security, whilst at the same time providing for Armenia’s security.