In this article, the authors speak to the paradox of assessing transformative learning (TL) in higher education. TL theory, developed by Jack Mezirow, is a theory of learning to describe the process of change in how individuals view the world based on previous experiences. Recognizing that the 10 phases of Mezirow's TL theory are fluid and intertwined, three prominent aspects resonated within the individual narratives: the importance of a disorienting dilemma, the qualities of self-reflection, and liberatory actions. By exploring the complexities, challenges, and possibilities encountered in their classrooms, the shared narratives reveal how students were engaged in TL and embedded within are holistic assessment processes the authors enacted with learners. Throughout this dialogical narrative inquiry focused on assessment, the authors underwent their own TL in the presence of each other, confessing uncertainties and vulnerabilities, thus showcasing the potential to transform understanding with and through reciprocal learning.