This chapter begins with a brief review of the Soviet approach to the Middle East and a discussion of how Putin’s approach differed from it before the outbreak of the Arab Spring. It then describes how Moscow at first attempted mainly to accommodate the forces unleashed by the Arab Spring but then turned against them over the course of 2011. After that, how Putin has adapted Russian foreign policy to the post–Arab Spring environment in the Middle East is discussed. The chapter concludes with an analysis of the strengths and weaknesses of Putin’s seemingly contradictory foreign policy toward the Middle East since the Arab Spring, and what challenges it might face in the future.