Through an ongoing study at an AACSB Jesuit, Catholic University with a strong focus on teaching, business student perspectives regarding online versus face-to-face courses indicate that students prefer face-to-face classes. Researchers have noted changes in student perspectives over time. A student’s perception of their own technological understanding may impact upon their perception of online and face-to-face education. Past research demonstrated a difference in student perceptions as the student took more online courses. This research explores the impact of a student’s self-reported technological understanding and taking more online courses. This research has implications for instructors and administrators.