The article examines the influence of educational attainment and enrollment on second births in Estonia, comparing Estonia's native population with immigrant population, which entered the country during the Soviet period and has mostly Russian/Slavic background. Furthermore, it compares the patterns before and after the onset of societal transformation of the 1990s. This allows us to analyse two different population groups that share the dynamics of the same socio-economic situation. Regarding education-fertility relationship, many Northern and Western European countries have shown a positive relationship between female education and second births, but in Central and East European countries the relationship generally seems to be negative. Estonia offers an interesting case where both patterns can be observed. While highly educated native women show high second birth intensities, highly educated immigrant women follow the East-European pattern. In the state socialist period, after controlling for the influence of other characteristics, including activity status and the partner's education, native women with tertiary education featured higher second birth intensity than any lower educational strata. In the post-socialist period, this difference has grown smaller but native Estonian women with tertiary education still display a significantly higher transition rate to second birth than their counterparts with secondary education. Highly educated immigrant women, however, exhibit lower second birth intensities than the less educated. That is, their behaviour is closer to population processes of their country of origin. 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 event history analysis employs microdata from the Estonian Generations and Gender Survey of 2004-05.