The growth of cooperative relations between Syria and Turkey, after the two countries came to the brink of war in 1998, has been a major development in the Middle East. This article examines both the reasons behind increasing ties between the two countries and the new challenges this rapprochement is facing due to the rapidly shifting international context. It argues that although systemic factors have been crucial in setting up the parameters of the bilateral relationship, these factors gain meaning through the complexities of domestic settings. The US policy of regime change and the Iraq War of 2003 and its aftermath are taken as the main regional and international factors influencing relations between the two countries since 1998. Domestic factors like the process of regime consolidation in Syria under Bashar and rising nationalism, the Kurdish issue, and the coming to power of the Justice and Development Party in Turkey constitute the main lenses through which these systemic factors are evaluated and policy outcomes projected.