This dissertation was developed in response to a long-standing imperative for teachers and scholars of writing: the need to meet students where they are (technologically) and keep up with emerging writing technologies. Said differently, when an emerging writing technology comes on the scene, teachers of writing tend to develop theoretical and pedagogical approaches for students' use of that technology in the writing classroom. While the imperative to keep up is well-meaning, the attempt can feel futile or, at the very least, pedagogically frustrating. This frustration is often fueled by permanent innovation, or when a culture’s technological innovation outpaces its ability to adapt to and for those technologies. To address the ever-evolving difficulties inherent within the relationship between writing, developing technologies, and teaching writing, this dissertation offers the field of Composition a path through the futility and frustration represented by keeping up. I call this intervention Composition’s “Technological Boneyard,” or more simply, “the boneyard.” The boneyard is first and foremost a metaphor, an imagined dumping ground that contains the obsolete, trashed, and forgotten technologies of writing that Composition has used and discarded in its move toward its raison d'être: the study and teaching of writing. Brimming with obsolete and discarded technologies of writing—like the first personal computers, floppy and hard disks, keyboards, and early mobile devices—the boneyard allows Composition to (re)investigate its technological and techno-pedagogical history, as well as its current relationships with developing technologies and writing. Through two qualitative case studies, this dissertation investigates the technologies in the boneyard and considers how abandoned, obsolete, and forgotten writing tools have shaped (and continue to shape) the teaching of writing in higher education, as well as Composition’s own history.