In this article Gary Hepburn and Jan Buley outline different approaches to implementing open source software (OSS) in schools; they also address the challenges that open source advocates should anticipate as they try to convince educational leaders to adopt OSS. With regard to OSS implementation, they note that schools have a flexible range of options: Schools may adopt selected OSS applications while retaining proprietary operating systems such as Windows or MacOS, they may install Linux as an optional open source alternative to Windows or MacOS, or they may adopt an "all open source" approach that relies entirely on Linux and OSS applications. In arguing on behalf of a given technological approach to OSS implementation, however, advocates will need to anticipate the socio-political barriers that will face them. These barriers include lack of awareness about OSS among educational leaders, systemic factors that prevent stakeholders from fully understanding the financial benefits of OSS, anxieties about the impact of change, unfamiliarity with the ethical dimensions of OSS, and an insufficient degree of OSS experience on behalf of technical support staff. By anticipating and addressing these issues, Hepburn and Buley argue, advocates as well as researchers will be able to promote OSS in a more focused and strategic fashion in the years to come.