This article examines the influence of educational attainment and enrolment on second births in Estonia, comparing the patterns before and after the onset of the societal transformation of the 1990s. While many Northern and Western European countries have shown a positive relationship between female education and second births, this pattern has not been found in Central and East European countries. Against that background, Estonia offers an interesting case with noticeably high second birth intensities for highly educated women. In the state socialist period, after controlling for the influence of other characteristics, including the partner's education, women with tertiary education were found to have higher second birth intensity than women from any lower educational strata. In the postsocialist period, the difference has grown smaller, but women with tertiary education still display a significantly higher transition rate to second birth than their counterparts with secondary education. Following the presentation of empirical findings, the article discusses the mechanisms that could underlie the observed relationship between education and fertility decisions in the changing societal context. The analysis employs microdata from the Estonian Generations and Gender Survey (GGS), conducted in 2004-05.