Abstract Moscow is one of the largest capital cities in the world, and one with a longstanding legacy of city planning. The city has an imposing physical presence and vitality. In the 1990s city planning for Moscow has had to adapt to the collapse of the Soviet system, meet public expectations of more democratic processes, and meet the demands of a free market economy. This article examines the significance of the Soviet legacy, recent changes in the legal, administrative and urban governance framework for planning, and strategic planning issues facing the metropolis. After a preoccupation for decades of trying to restrain the growth of Moscow, its planners are now attempting to address the prospect of continued population decline and other urban issues which are now characteristic of large capitalist cities. The article concludes that Moscow is at a critical turning point, moving from being a socialist to a capitalist city.