Free improvisation avails itself of philosophical meditations as it invites conjecture about what music actually is. As such, students’ responses to engaging with it are mixed. This chapter explores the challenges and benefits of teaching free improvisation in an undergraduate context but in doing so considers fundamental questions about what music is and what it can achieve. The idea of freedom and all its ramifications is invested in the activities of participating in free improvisation. The intention of introducing free improvisation to an undergraduate is not polemic, but the first year of an undergraduate program is a good time to consider polemical ideas. The cooperative and collective nature of free improvisation does not always fit well with a traditional teacher-student relationship, where knowledge is imparted by the learned to the learner. Improvisation, especially untethered from musical genre, is a tool that is applicable across many areas of artistic practice and, one might say, life.