In recent years, Türkiye’s relations with Russia have not been free from turbulence, but Ankara and Moscow have been able to maintain the relationship based on strategic calculations. The main aim of this article is to analyse how Türkiye’s transactional relationship with Russia has functioned in the context of the recent conflicts in their neighbourhood: the war in Ukraine and the post-war security architecture in the Karabakh region of Azerbaijan following the Second Karabakh War in 2020. This article argues that Russia’s war in Ukraine creates not only risks for Türkiye, but also a wide range of opportunities to boost its economy and regional posture. In particular, Moscow’s weakening military power gives Türkiye a chance to enhance its role in the post-war security architecture in the South Caucasus region.