The purpose of this study was to explore secondary education transition failure and dropout in the context of the UN Sustainable Development Goals on access to quality education. Two case studies were conducted for Uganda and Bangladesh using representative sample surveys and qualitative exploration. Country specific socioeconomic context and education system initiatives were considered in explaining the findings. Influencing factors included poverty, parental education, early marriage, social insecurity, scarcity of youth employment, as well as low quality education. The report provides recommendations for system improvements.