This study of female employment and family choices in Poland and East and West Germany from 1945 until 1989 seeks to make sense of the consequences of the communist half-century for the family and economic structures of eastern Europe. Taking issue with a simple dichotomization of liberal market versus socialist economies, this paper responds to claims that socialism was liberatory for women with contemporary data. Drawing on World Bank data and Malgorzata Fidelis’s study of postwar female labor in Poland, this paper examines the trajectory of standard indicators of gender equality and family structure and found no straightforward relationship between fertility, female employment, and histories of state socialism or liberal market economy. The changing conditions of postwar East Germany and Poland, as well as the economic shocks of the early 1990s, caused conditions that both impeded women’s ability to determine their own labor dynamics and provided new ways for female laborers to be active agents in determining their role and identity in newly organized societies. “Liberation” for women who worked and lived in postwar Central and Eastern Europe is not something so easily defined or measured. This study shows the subtle ways policy can shape family lives and render the line between emancipation and marginalization astonishingly thin.