Set in English Language Arts, this article takes up recent trends in literacy toward investigating ontological notions of digital texts. Two teacher educators recently implemented a series of readings and activities in their methods courses designed to help preservice teachers sophisticate their conceptions of texts beyond autonomous, neutral collections of information by considering digital age ideas such as software theory, textual ideology, and the algorithmic bias of the Internet. The authors review recent scholarship surrounding the integration of computational thinking and the humanities before illustrating a theoretical framework that combines software-driven interpretation and critical media literacy. Descriptions and applications of course texts and exercises precede a discussion on typological methodology. Through the analysis of semester-long writing reflections and course interactions, a typology of preservice teachers is then presented, illustrating three archetypes: Strategists, Hawkeyes, and Improvers. These archetypes are taken up to analyze the ways in which a range of teacher candidates considered ontological notions of digital texts to analyze instructional techniques, to sharpen their critical lenses, or to gain greater understanding of ELA as a discipline (or some combination of all three). This work demonstrates that as teacher educators and teacher candidates increasingly consider software-powered literacies, interrogations of who we are, who we are becoming, and what it all means requires attention to, and explicit practice with, the dark side of digital texts.