Russia has not specified its national interests in the Middle East or the Arab World since the 1990s. This paper discusses Russia’s shift toward a more active and effective role in the Middle East, in particular after Vladimir Putin came to power. Putin’s attempts to strengthen Russia in the Middle East were driven by a mixture of nostalgia and strategic national interests. With the events of the Arab Spring, Russia sensed that Arab revolutions could result in geostrategic changes in the region, which may not comply with its growing ambitions. It is this background against which Russia’s different stances toward each Arab Spring country and the outcomes of their respective uprisings can be read. Putin expressed anti-change reservations in Libya and Egypt, and even more so in Syria, making it one of the major actors in the Syrian crisis. At the same time, however, Moscow had no strong stance on Yemen, Tunisia, or Bahrain. The motives behind Russia’s role can be understood through a look at its internal situation, which is being influenced by waves of democratic change in the Arab Region, as well as its impact on the future of Central Asian countries, particularly Russia’s allies (Azerbaijan, Kazakhstan, Tajikistan, and Belarus). This paper discusses all of these entanglements in the context of the current Arab situation.