In New Zealand the recipe for creating bilingual and biliterate Maori-medium graduates is not well understood because, for the most part, schools are left to their own devices to experiment with Maori and English language components. It is therefore not clear whether graduates reach high levels of bilingualism and biliteracy, and ultimately, whether or not they are prepared for the world outside school. This study followed five Maori-medium primary school graduates for 3 years after they decided to transition to English-medium secondary schools. Of particularly interest was their academic English language preparedness, the extent to which schools continued to nurture their Maori language growth, and how well the students coped in the school culture. After 3 years at secondary schools the outcomes were positive. The students settled in well, and academically, all five had passed the compulsory national examination programme for year 11 students. However, specific challenges to academic English were a continual issue for some, including the areas of spelling, essay structure, vocabulary use, and the language of mathematics and science. Also, their Maori language was suffering. This study concludes that while Maori-medium education has prepared these five students well to transition to English-medium schools, greater preparation is required to support them with academic English as well as particular attention to nurturing and maintaining Maori language learning.