This article develops a framework for this special issue of "JTE," and assesses the assessment of transformative learning. What and whom are the contributors assessing? For what ends? And how effectively? The call for manuscripts cited two "megatrends" in the transformative learning literature: (1) the importance of deep and transformative learning experiences that profoundly affect adult learners' sense of self and their relationships and behavior in their community and broader world; and (2) the need to clearly document these learning experiences and interventions and rigorously assess their outcomes, both proximal and distal. In what follows, I pose questions that these trends suggested to me and use them to take stock of transformative learning theory and education in the 21st century. At the end of each section, I synthesize what I found to be relevant from my review of the articles in this issue, highlighting what I see to be major contributions.