Our critical historiography of e-learning policy in Ontario, Canada, traces the policy's trajectory through three settlements (2006-2022) and shows how successive governments have mobilized neoliberal discourses of personalization, access, and choice to justify new arrangements with private actors, within a broader sociopolitical context that includes increased privatization and commodification of public institutions, cuts to public spending, and imagines individuals as rational subjects driven to maximize their economic potential. This context exacerbates challenges students marginalized by schooling already face. Findings from our critical discourse analyses of government documents and news media reports also demonstrate that online learning in Ontario is neither personalized nor customizable but instead is centralized, standardized and, by design, operates independent of rather than interdependent with community. Further, our findings highlight the interdependence of schools -- online and in-person -- with social processes that create and perpetuate inequality, including gendered and racialized poverty, locally and abroad.