In the view of an apparent change in balance of power in Syria in 2017-2018 the challenges of reconstruction of the territories affected by a durable and highly destructive conflict have quickly risen to the forefront of the international agenda. A sheer scope of physical damage and humanitarian crisis in the country and a catastrophic lack of financial resources needed to mitigate consequences of a military confrontation and come back to normal life leave no doubt that the reconstruction process will imply a considerable external support. This paper identifies the particularities of Russia’s and the Western countries’ approaches to Syria’s reconstruction based on available public sources and their respective perceptions of related political dilemmas. Such a comparison has been made neither by Russian scholars who have touched upon the reconstruction agenda only sporadically or examined only the Russian motives, nor by foreign experts who have not studied the Russia’s initiatives scrupulously yet. The first section summarizes publicly available information about the bilateral Russian-Syrian dialogue on reconstruction and the main dimensions of the Russian efforts aimed at ensuring a more active engagement of the established donors in reconstruction of Syria. The second section examines the origins and a subsequent evolution of the key representatives of the ‘Group of Friends of the Syrian People’ (primarily, the U.S. and the EU countries) positions on rebuilding Syria. Special attention is paid to identifying similarities and differences between the circumstances surrounding Syria’s reconstruction and the international context around implementation of other large post-conflict reconstruction programs, primarily in Iraq and Afghanistan. The conclusion is drawn that ‘mutually assured obstruction’ and the development of two parallel reconstruction processes to the west and to the east of the Euphrates River will have an extremely negative impact on both Syria and a wider region. Prevention of this scenario entails a wide range of reputational, economic and political-strategic risks for all actors inside and outside Syria.