There are only a few approaches in socialization theory that give empirical insights into the processes of growing up in an autocratic system. However, political regimes like the former German Democratic Republic (GDR) have (had) only limited control over private family structures. Thus, the different family backgrounds of women who were part of the opposition movement and imprisoned because they tried to (illegally) migrate to West Germany will be illustrated in this paper. The study consists of biographical narratives with women born in the 1940s, ‘50s, and ‘60s. The very different family backgrounds of these women influenced the acquired strategies to deal with the autocratic system. However, these strategies can fail or become ineffective in different life circumstances leading to biographical blockades. I argue that biographical blockades can be considered as a key concept to explain high-risk emigration decisions.