This qualitative study explores moments within four individual psychotherapy supervision processes that were experienced by supervisors and supervisees as crucial in terms of change. A multi-case study design was applied, and multiple sources of data were analyzed. On the basis of a constant comparative method, the following themes were identified that appeared in the same order within all moments of change: increasing tension, unexpected move and uncertainty, reestablishing connection, and new insights and plans. The study then tested the hypothesis that the themes contain elements of affect regulation, defined as attunement, disruption, and repair. To test this hypothesis, the four themes were first analyzed descriptively, and then coded for emotional expressions. The results confirmed the presence of affect regulation in every theme. The findings have significant implications for understanding and teaching psychotherapy supervision.