Over the last two decades, the high profile of awards of excellence in Canada has thrown a spotlight on the question of architectural quality, especially in the design and construction of cultural institutions. In this period, the profession and discipline of architecture have faced the rise of two major paradigms: the imperative of environmentalism and the advent of new digital technologies have both led to radical changes in conceptual frameworks. It is our hypothesis that these major shifts have influenced the judgement of quality in our built environment and public buildings. We propose to make them explicit, theorising them through a series of comparative analyses of Canadian awards of excellence. How have the criteria of quality been established in Canadian awards since 1995? How is architectural judgement oscillating between the meaning of forms and environmental performance, symbolism and innovation?