This essay examines contemporary digital educational assessment and argues that there are underlying problematic values and consequences entailed by the datafication of education as coupled with assessment practices. By applying Dewey's work concerning curriculum, aims, growth, and the conception of democracy through education to current methods, this examination exposes digital assessment as perpetuating a cruel optimism through assessment that undermines democratic, progressive functions of education. Dewey's philosophy provides a perspective from which to repurpose digital tools in a manner that fosters, rather than hinders, aims, growth, and democracy in education.