The article discusses the failing history of Transcaucasia (South Caucasus) integration and the reasons for its continued failures. Lack of positive experience in integration, constant rivalry between the states of the region and among the great powers around the wider region and extra-regional powers, absence of common identity, and contrary security perceptions by the regional players have all played a part in these failures. Conflicts between countries in this region or with ethnic enclaves, as well as tensions with bigger neighbors have hindered regional integration processes. In this light, the attempts for normalization of Armenian-Turkish relations have the potential to be an essential factor for future successful regional integration. That failing, any integration hopes in Transcaucasia would be delayed for long.