The growing impact of globalisation and the development of a ‘knowledge society’ have led many to argue that 21st century skills are essential for life in twenty-first century society and that ICT is central to their development. This paper describes how 21st century skills, in particular digital literacy, critical thinking, creativity, communication and collaboration skills, have been conceptualised and embedded in the resources developed for teachers in iTEC, a four-year, European project. The effectiveness of this approach is considered in light of the data collected through the evaluation of the pilots, which considers both the potential benefits of using technology to support the development of 21st century skills, but also the challenges of doing so. Finally, the paper discusses the learning support systems required in order to transform pedagogies and embed 21st century skills. It is argued that support is required in standards and assessment; curriculum and instruction; professional development; and learning environments.