The COVID-19 pandemic has disrupted our collective normal patterns of behavior in almost all aspects of our personal and professional lives. While many K-12 and post-secondary subject area curricula lend themselves more easily to a migration to online and remote learning, technology education faces unique challenges. This research paper sought to understand the challenges, benefits, and lessons learned through an analysis of the process of re-organizing a pre-service technology education diploma for remote, blended, and face-to-face learning during the early stages of the COVID-19 pandemic. The investigation followed a collaborative autoethnographic methodology as the authors constructed two narratives based on their roles of administering and instructing in a pre-service technology education diploma program. An interpretive descriptive analysis suggests a number of challenges associated with the organizational changes, but also a number of positive outcomes related to the instructional shifts. Challenges included maintaining equitable access to physical materials and technologies for all students, scheduling issues related to changing pandemic rules and regulations, and a loss of social presence with students. Benefits included more student autonomy, less dependence on group work for technical skill development, and the development of alternative delivery models for pre-service technology education that could be used to expand program offerings to non-traditional students.