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Although South Africa's total fertility rate is fewer than three births per woman and declining, early childbearing remains high. Limited data in developing countries, particularly the lack of information on timing of events, has made it difficult to investigate how early life characteristics affect young-age childbearing and schooling. We take advantage of a unique panel dataset to examine the dynamics defining early childbearing and the factors facilitating school enrollment after childbearing. The Cape Area Panel Study (CAPS) is a survey of 4,752 young people in Cape Town that also includes a calendar with extensive retrospective information. We found that young mothers who were weaker students prior to giving birth were less likely to enroll in school subsequent to giving birth. However, a significant proportion of young mothers managed to continue with their studies, particularly African girls. This suggests that well-focused policies are likely to have an impact on the number of young mothers who exploit the opportunity to enhance both their education and their subsequent earning and employment opportunities.