This article presents a case study of an online class in technical and professional communication pedagogy (the teaching of technical and professional writing) that uses digital video technology for discussions. Because students in the class share their experiences using the video technology, the study uses a collaborative autoethnography framework to learn if the digital technology, Flipgrid, would enhance students’ experiences with discussions in an online class compared to their experiences with discussions on traditional discussion boards. Providing such exposure to a new technology tool can help students gain the confidence that is necessary for learning new technologies in the workplace. When the technology did not provide the hoped-for results after a few weeks, the class stopped using it, returning to the traditional discussion board in the learning management system, which can be more effective when teachers participate and organize students into small groups. Reflecting on what happened, students in the class collaborated on this article to share their experiences.