Although supporting and promoting democracy has traditionally been a key theme of the EU’s external action, its record in that domain has been mixed. This has been partly attributed to both the challenges of promoting democracy in general as well as the adequacy and efficiency of the EU’s tools. At the same time, questions have been raised about how serious the EU actually is in promoting democracy, and to what extent its policies have been shaped by trade-offs between, on the one hand, norms and principles and, on the other, interests. In that context, a growing literature has been examining how EU external action and democracy promotion are shaped by concerns related to security and stability. Seeking to contribute to a better understanding of these dynamics in the EU’s engagement with the South Caucasus, this working paper zooms in on the cases of Armenia and Georgia, two EU neighbours that have been undergoing substantial change over the past two decades – both in terms of their geostrategic trajectory as well as their domestic political dynamics. The paper argues that the EU has generally been reluctant to criticise and counter autocratic tendencies in both countries over the past two decades, and that this was usually at least partly linked to four key security and stability considerations: Maintaining or not undermining domestic stability in the two countries, stable and constructive relations with both countries’ governments, regional security as was as the EU’s geopolitical interests. This is not to say that these considerations were the only or even the main causes for the lack of action or stronger rhetoric. The EU’s reactions were also informed by a general lack of attention, bandwidth and capacity given various domestic and external challenges the Union faced over the past two decades. This notably affected its relations with Armenia, which never received quite as much attention as post-Rose revolution Georgia to begin with, and even less following its 2013 decision not to sign an Association Agreement with the EU and join the Russian-led Eurasian Economic Union instead. At the same time, the most problematic developments in Armenia were at least partly overshadowed by other issues that incentivised the EU to adopt a less critical stance to the regime. In 2008, a fraudulent presidential election was followed by protests that were brutally cracked down, leaving ten people dead. If the EU’s reaction was rather muted, this might have to be seen in the context of its strong support for and encouragement of the Armenia-Turkey rapprochement in 2008 and 2009. Similarly, the 2015 Armenian constitutional referendum, which was widely seen as a vehicle to allow President Serzh Sargsyan to stay in power beyond his term limit, occurred in the context of increasing tensions and border clashes between Azerbaijan and Armenia. Finally, the EU’s reaction to developments that risk undermining the positive evolution that Armenia has taken since the 2018 Velvet revolution needs to be seen in the context of both the escalation of the Azerbaijan-Armenia conflict since 2020 as well as Armenia’s subsequent gradual geopolitical reorientation from Russia towards Europe and the West. While Georgia received more attention than Armenia, the EU’s reaction to democratic backsliding within the country followed a similar pattern. Before 2024, the EU was reluctant to criticise Georgia’s gradual, but increasing, autocratisation. This seems to have been informed by the perception that consecutive Georgian governments appeared keen on joining Euro-Atlantic structures and that EU influence was most efficiently pursued through constructive engagement. In that context, the 2004-2013 Saakashvili presidency was generally given the benefit of the doubt when it came to its democratic credentials because of its radically pro-Western orientation, the dramatic domestic challenge of fixing a failing state as well as the equally dramatic external challenge of Russia infringing on its territorial integrity. This EU tendency continued under successive Georgian Dream governments. Actual and perceived progress in functional cooperation between the EU and Georgia overshadowed democratic stagnation and backsliding, even when it became ever more obvious and egregious in the late 2010s and early 2020s. The EU’s soft approach and its decision to grant Georgia candidate status in 2023 were also informed by the objective of keeping Russian influence in check. The EU only changed its approach in 2024, when the Georgian government’s rhetoric became overtly hostile and its action more extreme all the while both rhetoric and action became harder to ignore given Georgia’s status as a candidate for EU membership from December 2023 onwards.