The article examines the geopolitics of transport communications in Central Asia and the Caspian, and Kazakhstan’s energy policy. Kazakhstan suffers from geopolitical isolation and preoccupied with identifying new inroads to foreign markets. This has become the main focus of its energy policy. Despite involvement by the Western countries, China, and Russia in regional energy geopolitics, Kazakhstan faces tough geopolitical choices. Astana is still in search of an effective energy policy that would enable further diversification of its transport communications. The existing transit routes for the Kashagan oil, as proposed by Russia and other external actors, do not fully support the energy security of Kazakhstan. As for Kashagan oil field production, the article concludes that the main obstacles include several complicated issues such as technical problems, as well as risks to the environment of the Caspian Sea. The new context, namely the dramatic decline of oil prices and its consequences for the global economy, makes it difficult to project a clear vision for the project’s success.