In its essence, transformative learning is a dynamic and ever-emerging process, according to the core literature that deals with it. As such, when examined from the perspective of teacher professional development, transformative learning ceases being solely related to an individual and becomes a composition within which the individual creates and expands forms that need change. Thus, teacher learning that focuses only on new technology, methodology, and classroom management remains informative and valuable, but without a transformative character. This paper explores the underpinning principles of transformative learning by observing the notions of transformative change from the perspective of two non-traditional schools: one in Hungary and the other in Portugal. As such, the analysis and conclusions are formed using the data collected through a qualitative inquiry of teachers and principals from the two selected schools. The results suggest that teacher transformative learning in the two specific settings is intimately related to the awareness and need of change in education provisions, as well as with the challenges that this change brings. The gathered insights pave a way to a better understanding of the intricate and delicate tapestry of teacher learning in occasions in which it embraces an everlasting reflective and transformative character.