"Cruel optimism" is a term coined by Lauren Berlant. In conceptualizing this term, Berlant draws on the resources of critical theory to interrogate people's desires for things they think may improve their lot, but actually act as obstacles to flourishing. This notion may be useful for analysing the current state of education in Australia, and the desire to believe that "My School," and the associated data it provides, will enable schools to address social inequalities. For Berlant, the promise of such technologies is problematic because it diverts our attention from important ethical, social and political questions, some of which are highlighted in the contributions to this special issue. Using "cruel optimism" as a point of departure, I interrogate how the notion of critical theory has been conceptualized in educational research by briefly looking at scholarship within and outside education relating to critical theory. Following on from this, I consider how what I am terming critical theory is put to work in each of the articles that make up this special issue on "My School."