Beyond the headline-making S-300 missile deal, the international nuclear agreement with Iran poses a multifaceted strategic dilemma for Russia. Iran’s potential de-isolation will necessitate a speeded-up rebranding of Russia and more policy acrobatics, among which reacting to the new dynamics in the energy market will be the most challenging. It is becoming imperative for Moscow not to close options in the Middle East: adopt softer stances, make obscure moves, and avoid camps, especially the Iran-Syria one. In the post-Soviet neighbourhood, Iran’s clout, powered by a probable cycle of economic growth, is likely to increase, pushing Russia to make adjustments as well. While preoccupied by softly limiting Iran’s influence, Russia might use the de-isolation of Iran to legitimize the Eurasian Economic Union, seal off the Caspian Sea from the West and keep the rising Chinese influence in Central Asia in check.