When students have the freedom to use digital media to create, communicate and disseminate messages, distinctly carnivalesque and transgressive creative projects are often part of the mix. In this paper, I situate in-school youth media transgression in the context of pedagogical theories of participatory culture, art education, and digital and media literacy education. Using interviews with five experienced high school media production educators, I examine how educators perceive school situations where behavior or student media work products are transgressive. 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. They perceive creative control to be a negotiation between students and teachers on issues of content, format, production and distribution processes.