This article reports on face-to-face and online qualitative research conducted with 25 teachers from 8 schools in Australia that explored their experience of mindfulness and reflection in relation to a self-identified relational dilemma with a student, colleague, or parent who was causing them concern at work. The aim of this study was to find out whether teachers’ practice of mindfulness led to increased insight into their dilemma through helping them to be more self-aware and conscious both of their behavior and of their own innate inner wisdom. In the majority of cases, by the end of the 6-week project, the dilemma was no longer experienced as a dilemma or the teachers’ relationship with it had changed. There is a need to conduct more research with a longer time frame to explore the potential of mindfulness and reflection to contribute to sustained personal, professional, and institutional renewal and transformation in education.