This paper uses new survey data containing retrospective life history calendars for South African youth to analyze the dynamics of grade advancement and family living arrangements. The analysis is based on the first wave of the Cape Area Panel Study, which surveys 4800 respondents age 14-22 in metropolitan Cape Town. While previous research has suggested that grade repetition plays a major role in explaining school outcomes in South Africa, this is one of the first large household surveys to provide detailed information about grade repetition. Preliminary results indicate that males are twice as likely to repeat grades at early ages, with grade repetition explaining most of the growing female advantage in schooling in South Africa. The paper will use the data to analyze the impact of variables such as race, gender, parental schooling, and family structure, on grade repetition, school enrollment, and cumulative grade attainment.