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In the tracked educational system of the Netherlands, students at the end of secondary education have to decide whether they want to enter subsequent post-secondary or tertiary education. Depending on the previous qualification, they have the choice between up to four different options, including not entering further education. We propose, in line with prevalent theoretical approaches, that children from lower socio-economic backgrounds tend to make decisions that do not fully capitalize on their previously obtained qualifications. By means of multinomial logistic regression models we tested the unconditional and conditional effects of family background for entering the different tracks of post-secondary education. In the unconditional analyses we found effects for parental education on making a transition to all types of post-secondary and tertiary education, but the occupational status of the father seems to be only relevant for the transition to lower tier tertiary education. The conditional effects of parental education for making the transition to senior vocational education and university are strong, while the transition to lower tertiary education is not influenced by parental background characteristics. This shows that even with eligibility for the most prestigious tracks, children from lower socio-economic backgrounds tend to make less ambitious educational decisions. We also examined to what extent this inequality changed across time for the cohorts that terminated secondary education between 1932 and 1995. Decreasing effects of parental education indicate that the expansion of secondary education had the positive effect of leading more children from lower social backgrounds into favourable secondary education tracks, especially the intermediate general track. This equalization is carried forward through the entire sequence of educational transitions. The students from advantaged backgrounds nevertheless still profit from the parental resources in access to the most prestigious tertiary education 123High Educ (2010) 60:85-100 DOI 10.1007 institutions given secondary qualifications. Their head start into the academic track has not been reduced across cohorts.