This article explores the affective and situated aspects of enacting public schooling within a burgeoning economy of digital platforms. Drawing on a series of conversations with two teachers and two school leaders at a Danish primary school, the article examines how the increasing involvement of educational platforms in schools reshapes who and what matters in the everyday life of the school. The article highlights different ways in which platforms entangle with educational practices and relations beyond their functional promises to save time, promote efficiency, solve administrative issues, and other related tasks. As generative forces based on relocating educational phenomena within a proprietary digital architecture, the analysis illustrates how the involvement of platforms becomes co-constitutive of new forms of affective attachments and loyalty that challenge historical configurations of pluralism in public schools. Drawing on these constitutive effects, the article introduces Lauren Berlant’s notion of cruel optimism to discuss the implications of sustaining public schooling within a largely unregulated economy of platform subscriptions. The article’s discussions call for closer political and scholarly attention to the educational consequences of enacting school within the economic conditions of current platform capitalism.