This grounded theory study explores how the post-conflict transition in the aftermath of the Cold War is remembered in Eastern German families across generations with and without experiential memories. The dataset consists of seven in-depth intergenerational interviews with families living in Eastern Germany, which were conducted in Thuringia during April and May 2018 in an anthropological research. The inductive approach to the analysis in this study is informed by Bernard’s adaption of the grounded theory methodology (Bernard 2006). Therefore the understanding of the memory of the transition is grounded in the perspectives of the participants living in Eastern Germany. In the analysed interviews, the parental generation’s vivid memories of the transition as an ambivalent and personally formative time stood in a stark contrast to the young generations struggle to conceptualise the transition at all. The major discrepancies between the ways parents and children remembered the transition suggest a selective intergenerational transmission of the memory. In the analysed data, the participants replaced the memory of the transitional process with a direct comparison between memories of the GDR and the present or decontextualized experiential anecdotes from the transitional time, which produced communicative silence on the transition within the interviewed families. As a result, the meaning, the transition has for the parents, is lost in the next generation, which according to the participants’ reflection is stimulated and assisted by the cultural memory of the system change.