This article discusses the didactical challenges and opportunities of driving simulator supported teaching and learning, mediated through digital technology in vocational educational and training through the example of driving simulators. We highlight relevant research on simulator-supported teaching and the need for practice-based, empirically driven research. The study is part of a larger project that focuses on the implementation of simulator environments in three secondary schools in the natural resource programme. The data consists of three action research projects in two of these schools where vocational teachers, together with researchers, plan and implement teaching with driving simulators as a new technology in their practice. The article is an example of how action research can contribute to critical evaluation and development of teachers’ professional work during the implementation of new technology. Results from these projects are analysed using the TPACK framework. The vocational teacher has a central position to ‘master’ the digital tool. Issues about fidelity, transfer and progression are discussed in terms of concepts that are challenged when new technology is introduced. Here, the vocational teachers professional and content knowledge as well as the teacher’s didactic and technical competence are central for the development of new strategies when the conditions for teaching change fundamentally.