The declaration of the ‘end of the transition paradigm’ at the dawn of the new millennium provoked a rethinking in transformation theory, as it challenged the dichotomy of democratic and authoritarian systems and the ‘finality’ of transformation. This study contributes to the debate on hybrid political systems, critically assessing established theoretical models of political cul-ture and stability with a view to their applicability in the post-Soviet environment. On the basis of comprehensive field research, the study compares Georgia and Armenia as most similar cases, which inherited similar legacies from their common Soviet past but showed different developments of regime persistence, instability and democratization processes since gaining independence and sovereignty. While Georgia experienced ups and downs of its democratization efforts, Armenia was considered a stable semi-consolidated authoritarian system until the Velvet Revolution, which can be regarded as an important ‘reset’ in Armenia’s recent history. In a comparative approach this study analyses critical hues of stability in the political ‘grey zone’ while concentrating on the intermediary structure of both countries. Given its mediating function within the political system, the intermediary sphere of civil society actors and political elites instructively reflects the (dis)connect between citizens and the state. Focusing the analysis on the intermediary sphere provides valuable insights into the dynamics of political processes and decision-making, the articulation of interests independent from the state and the formation and recruitment of elites. By taking a critical look at the very constitution of the nexus of political elites and civil society as well as interlinkages and impacts, the major finding is that the mutual influence of political culture and political structure on stability can be confirmed in both countries’ context. Thereby, the study identifies key differences in regime configurations that impact persistence in the political grey zone.