This dissertation focuses on the dynamics between teachers and machines at the intersections of design, teaching labor, and pedagogy when automation is deployed in writing classrooms. The sites of analysis are Eli Review and Turnitin, two technologies that represent different design approaches that center around "informating" or "automating" data about student work. The exigence for this project emerges out of the labor crisis currently enveloping higher education. Traditionally, in times of labor crises, automation and machines are used to replace scarce or imperfect human labor. However, balanced and purposeful design of automated technology has the potential to enhance humans' labor and protect workers. Using holistic and provisional coding, combined with object interviews, this dissertation analyzes data collected from a national survey distributed to composition instructors and nine interviews about their personal experiences with Eli Review and Turnitin. The data and findings from these methods suggests beneficial relationships between humans and machines are possible in the writing classroom through careful design, integration, and management of educational and learning technologies. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]