Language tests, including international high-stakes English proficiency tests widely used around the world, are to be viewed as ideological constructs connected with power relations and center-periphery demarcations at different social levels. In this paper, we examine the International English Language Testing System (IELTS) as an instance of such tests to uncover some of its underlying sociocultural functions. Adopting a critical autobiographical approach that revisits three personal trajectories in relation to each other and in connection with wider contextual dynamics, we reflect on our own lived experiences of engagements with IELTS in various social and institutional settings and in different roles. Each one of us first shared narrative accounts of turning points in our learning, taking, teaching, and using IELTS within the past two decades. Then, we explored these narratives through multiple rounds of reflections and discussions of their common underlying ideas related to the sociocultural functioning of IELTS. Although the narratives presented unique trajectories, three common themes of Pain, Pedagogy, and Politics emerged from our collective analytic reflections. We discuss these themes and how they can problematize different aspects of IELTS from a critical point of view.