In 2002 a review of the educational and technical performance of the Virtual Schooling Service being tested in Queensland, Australia, was conducted. The service utilised synchronous and asynchronous online delivery strategies and a range of learning technologies to support students at a distance, who may otherwise have restricted choices in their selection of subjects to study in Years 11 and 12—the final and non-compulsory years of schooling where students are typically aged 16 to 17. An account of how Activity Theory was used to conceptualise the evaluation is provided. A focus on one element of the evaluation—pedagogical effectiveness—with case studies of actual delivery and receiving classes is incorporated to highlight the pedagogical limitations and potentials of the service. The “productive pedagogies” schema is introduced as a framework for the evaluation of pedagogical effectiveness of the virtual classes. Critical success factors for pedagogical effectiveness are documented, along with a reflection on these elements using Activity Theory. The chapter concludes with an update of the current initiatives being undertaken to enhance the pedagogical effectiveness of the Virtual Schooling Service.