In this article we highlight and discuss how norm-challenging pedagogy in music education can be encouraged and executed from three different angles. We primarily focus on activities such as democratic learning situations for pupils and teachers, to be explored as safe and brave spaces. With a starting point in norm-critical pedagogy, we explore the possibility of using norm-challenging pedagogy as, through and in music educational settings. Norm-challenging pedagogy as music education can challenge dominant ways of assimilating, processing, and expressing knowledge, whereas norm-challenging pedagogy through music education concerns how traditional views on, for example, gender, race, or disability identities can be challenged through music activities. Norm-challenging pedagogy in music education critically reflects on who has the right to learn and express themselves musically and in what ways, related to gender, race or disability. The article is based on a phenomenological view of aesthetic experience and music education as a life of equal value, where de Beauvoir’s concepts of freedom, facticity, and ambiguity constitute crucial analytical concepts. The author’s own experiences of ambiguous norm-challenging situations as, through and in music education will be used and discussed in relation to the philosophical framework. The results of the exploration will be critically reflected upon in relation to organisational, collegial, didactic and relational aspects of music education.