The theory of transformative learning has been explored by different theorists and scholars. However, few scholars have made an attempt to make a comparison between transformative learning and Confucianism or between transformative learning and andragogy. The authors of this article address these comparisons to develop new and different insights to guide Web-based teaching and learning. Indeed, as Web-based teaching and learning has become popular in the 21st century, the theory of transformative learning should help Web-based teaching and learning. The authors of this article demonstrate different ways whereby the theory of transformative learning can be used to stimulate critical self-reflection and potentially transformative learning.