This paper presents a personal picture of my long-standing association with the English language teaching and assessment situation in Hong Kong. The paper presents a 50-year retrospective of assessment in Hong Kong, through the lens of my 40 years in the territory and my personal experience of English language teaching, teacher education, and assessment. I present a historical and theoretical picture of how English language examinations have moved forward in Hong Kong, and how I was fortunate enough to be involved in the big changes which were taking place in assessment and English language assessment in particular. While the picture I portray through this paper is a somewhat personal one, it contributes to an understanding of how assessment reform has been forward-looking, and largely successful, in Hong Kong, painting a picture of how assessment development has complemented curriculum development. I suggest that it may be instructive for educators in other jurisdictions to consider the long-term picture of development in English language assessment reform in their own country with a view to analyzing their own perspectives of the relative success of policy changes and large-scale reforms.