The use of online learning and other software-powered technologies is on the rise in the United States, encouraged financially and politically by governmental and commercial entities. Specifically, online courses are gaining ground in K-12 public schools, schools which often purchase from third-party providers. After a decade in the New York City Department of Education as an English teacher and schools official responsible for a large-scale online learning programme, the author asks the question: How does the use of software-powered technologies like online learning affect the teaching of literature? In pursuit of this question, the author draws on concept from the field of software studies while adapting qualitative methods from multimodal studies to examine precisely how the nature of software (and the ideologies of those who create and sell it) are subtly influencing the teaching of literature.