When students have the freedom to use digital media to create, communicate and disseminate messages, transgression occurs. In this paper, I situate in-school youth production in the context of pedagogical theories of participatory culture, art education, and digital and media literacy education. Using interviews with four experienced high school media production educators, I examine how educators perceive school situations where behavior or student media work products disrupt or transgress expectations. Teachers experience student transgression as an essential dimension of the dialectic between creative freedom and creative control. They perceive creative control to be a negotiation between students and teachers on issues of content, format, production and distribution processes. Teachers conceptualize the distinctions between students who use transgression as a form expressive creativity, a reproduction of the tropes of mass media and popular culture, the result of novices making mistakes as part of learning, an attempt to gain social power and status among their peers, or a challenge to adult authority. Teacher reflection on creative control and creative freedom may inform the design of media production learning experiences.