South African and international household and education datasets are analysed to characterise patterns of dropping out, grade repetition, academic under-performance and under-preparedness for post-school life in South African secondary schools. A number of measurement error problems are moreover discussed and in some cases remedied. The proportion of South African youths entering upper secondary schooling is above the trend found in comparable middle income countries, the proportion entering the last grade (Grade 12) is about average, but the proportion successfully completing secondary schooling (40%) is below average. The data suggest improving quality should be a greater planning priority than increasing enrolments. A what-if subject choice analysis using examination data moreover suggests that successful completion could be greatly enhanced by guiding students to more appropriate subject choices, possibly through a more standardised set of assessments in Grade 9. Any attempt to reduce dropping out must pay close attention to financial constraints experienced by students with respect to relatively low-cost inputs such as books. Teenage pregnancies must be reduced as these explain half of female dropping out. The quality problem in schools underlined by the fact that income returns and test score gains associated with each additional year of secondary schooling are well below those associated with a year of post-school education.