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The context of Malay Language (ML) teaching and learning in Singapore is laden with culture, social etiquette and history. Although the main working language is English, ML is constitutionalized as Singapore’s national language. ML teachers are specially addressed by everyone in the school, with the title “Cikgu” attached. It is within this unique classroom context that my investigation is focused. This research is driven by a deep concern about what effective learning looks like in an ML classroom, what teaching practices support this and what can be done to help ML teachers master these practices so that improvements associated with the latest assessment reform in ML education can spread and be sustained. This reform is Assessment for Learning (AfL) which was introduced into the ML (Secondary) syllabus in 2011. Other than conducting surveys and classroom observations, 20 in-depth interviews were conducted with selected teachers. The interviews aimed to discover the teachers’ habitus and degree to which they internalized AfL concepts and regarded it as important. The study produces an area of new knowledge regarding AfL: the influence of teachers’ early assessment habitus on their current assessment practice. One research implication is the awareness that ML teachers, policymakers and school leaders need to have of teachers’ own assessment habitus and the impact of habitus on teachers’ current classroom assessment practices.