In this article, the author looks back at over 30 years of experience with “Digital Humanities” and argues that while our media for research, delivery, have changed, our methodologies have not. That fact poses a significant challenge for Digital Medievalists because the author believes and advocates for a significant change not just in our delivery systems, but that the digital tools we now have should be changing the way we think and do research, teach, and advertise Medieval Studies as a whole. At once a personal story of experience in the field and an analysis of current practices, this article critiques practices frequently touted as innovative and the wave of the future as nothing more than the same old packages using a new delivery system that may or may not be as effective as the previous delivery system. This critique in the author’s view applies to our teaching as well as to our research. Finally, the author offers some suggestions for both research and teaching that attempt to break out of the old molds and methods and use the digital tools we have in innovative ways that do change the way medievalists research and teach and take fuller advantage of what working digitally offers the field.