Democratisation processes in the Western Balkans challenge main assumptions of transformation theory. Firstly, the Yugoslav successor states did not follow a linear path of transformation but found themselves in political grey zones. Secondly, transformation proved to be very much dependent on a country’s political, social and economic peculiarities. With regard to the evaluation of the quality of democracy these developments highlight the need to incorporate such considerations into the methodology of measurement. Paying attention to recent “anti-liberal” trends in East and Central Europe as well as evident crisis and backdrops in the democratisation of the Western Balkans the question of how such dilemmas related to the quality of democracy can be analysed and measured come to the fore. While many new indicators have been proposed over the past several decades none have been successful in arriving at a precise measurement of regional specificities and potential crisis occurring in the course of democratization. Most of traditional approaches in measuring democracy and the quality of democracy have been engaged in developing highly differentiated schemata and breaking down “democracy” into a rather large number of categories and indices. Departing from the analysis of the Western Balkans’ developments and specificities the paper propose an incorporation of contextual categories being able to grasp long-term democratization trends and better explain the relationship between external and internal factors on the one hand and the specific course of socio-economic development on the other, which both proved to be decisive factors for democratic developments in the Western Balkans. The paper will offer a comprehensive contextual analysis of the state of democracy in the Western Balkans and make an argument for introducing a contextual categories into measurement of democracy, which could make the already existing methodologies more sensitive for possible und unexpected developments and crisis in the process of democratisation.