The making of digital educational futures raises pressing social justice concerns. Against this background, scholars face the challenge of bridging the tasks of investigation and critical engagement. Inspired by French pragmatic sociology, this article presents the notion of "plural school worlds" as analytical anchor point for dealing with this double-task coherently and productively. Varying understandings of what makes 'good and fair school education' are identified as defining features of different school worlds. These understandings (1) are historically entangled with social and political orders, (2) inform how we envision, enact, and evaluate possible educational futures, and (3) define a shared discursive space for exchange between various groups of actors. We claim that the notion of school worlds thus furthers both our understanding of "persistent patterns of disadvantaging in digital education" and our "capacity for critical dialogue" with involved actors through "sensitizing explication," "shifting problematizations" and "reflecting performativity."