While questions surrounding the relationship between education and technology have captured the attention of philosophers of education in recent decades, such concerns have taken on new import. Particularly in the post COVID-19 educational landscape, EdTech has become bound up with power and ideology in ways that warrant ongoing scrutiny. Building upon the work of scholars who have shown that pragmatism can be sufficiently attentive to issues of power, I explore how a Deweyan critical pragmatism offers opportunities for philosophers of education to engage in normative debates surrounding the relationship between education and technology in the digital age.