After the “end of the transition paradigm” until today, research on the critical junctures and factors responsible for why states develop towards democratic consolidation or towards hybrid regimes remains scarce. Among the number of no longer autocratic regimes the relative share of hybrid regimes has constantly increased over the past two decades. While hopes were high regarding a sweeping wave of democratization after the fall of the Iron Curtain, first enthusiasm with regard to the Arab spring faded much faster – until today, researchers are reluctant to draw direct comparisons between the two regions. This paper, however, attempts to isolate context factors, notably with regard to the role of different domestic structures and actors as well as external democracy promoters, and to draw conclusions from the experiences of the transitions in Eastern Europe for why other cases of democratizing states develop towards democratic consolidation or regime hybridity.