The collapse of communism was a defining geopolitical event of late-twentieth century Europe, with well-documented economic, social, and political implications. Yet there is a striking absence of research on how it influenced divorce. The objective of this study is to provide an exploratory analysis of trends in divorce over the long transition from communism—starting from the decline of the communist economy in the 1980s and ending with economic revival—in seven countries: Bulgaria, Estonia, Hungary, Lithuania, Poland, Romania, and Russia. We discuss how the transition could be expected to either increase or decrease divorce risks. We analyze retrospective micro-level data on first marriages from the Changing Life Course Regimes in Eastern Europe (CLiCR) dataset. Based on our event-history analyses, we find that divorce rates increased in each country at some stage during the long transition and these increases cannot be explained by compositional change of the marriages. However, no uniform pattern emerged in the timing and duration of the increase in divorce risk. This striking variation leads us to conclude that even the effect of major societal ruptures is contextually contingent.