Working with students in ways that emphasize creativity and improvisation presupposes a posture of openness and self-regard for all stakeholders. The teacher in such a setting can neither impose an ideology nor fix expectations for growth. The students, composing and improvising collectively, will encounter opportunities to test beliefs and practice reflective thinking. Many questions are unresolved. How do students develop criticality in an open classroom? What assurances are there that they will choose projects that address justice, repair, and belonging? In this essay, I grapple with the limitations that confront a truly creative and open-ended music classroom. I fear that I cannot ensure criticality, though other rewards may attend its risk.