Schools are highly regulated sites of digital technology use. This article draws upon survey data from students (n = 1,174) across three Australian secondary schools, examining their experiences and perceptions of school regulation of technology use, as well as the ways in which students accommodate and/or work around such constraints. The data highlight a number of different forms of regulation that students perceive as impeding their in-school engagement with technology--most notably relating to filtering/blocking of content; (dis)possession of personal devices; enforced uses and standardized practices. Conversely, a number of tactics of contestation are also highlighted--including surreptitious uses of digital media; low-level "hacks" and technical reconfigurations; and various other forms of subversion. The article concludes by considering the implications of these findings, and the need for school authorities to work with students to develop negotiated forms of regulation that support expansive and increasingly personalized uses of technology within the school context.