Critical theory and transformative learning are two seminal theories that have incited a deluge of literature, fueled many discussions, and triggered much debate. Their relevance is enduring, and they are undeniably a great asset to the scholarship of adult education, but the two theories are far from fully developed or explored. Our purpose in this current article is to discuss critical theory alongside transformative learning theory and highlight their commonalities as we probe their connections and possibilities within adult education settings. It is our intention to contribute further thought and fuel ongoing critical analysis that may lead to further development of the two theories.