The development of digital information literacy (DIL) has been slow in comparison to changes in information communication technologies, and this remains an issue for the higher education sector. Competency in such skills is essential to full participation in society and work. In addition, these skills are regarded as underpinning the ability to maintain life long learning. Evidence suggests that simple exposure to technology is not sufficient to promote adequate levels of literacy. Why has DIL development been so slow? How can we speed the process up? The purpose of this study was to identify obstacles and supports to fostering the development of DIL to staff and students in higher education. The literature identified a range of obstacles that hindered students' ability to develop their technology related skills. The issue of access and the digital divide that has been of interest to those concerned with social equity continues to generate lively discussion. The students' own beliefs and attitudes to learning new technology can also become barriers to the students' learning progress when they experience low self-efficacy or anxiety about their ability to develop digital skills. Conversely, students who are over-confident regarding their technical proficiency can also be hindered in their ability to develop good digital information skills. Three broad strategies were inferred from the learning principles advocated nearly 80 years ago by Dewey as having the potential to support the development of digital information skills. The first of these was collaboration and sharing. While the benefits of collaboration were established decades ago, the advent of the Internet has made this a reality through online communities of practice. Dewey's advocacy of experiential learning has been widely applied on the Internet in the form of bricolage. Finally, personal relevance, the third of Dewey's principles, is an inherent part of the Web 2.0 tools that personalize online environments to the individual. Using a case study design, four higher education institutions ran 10 two-hour workshops in which participants were given autonomy over their learning and goals and were encouraged to collaborate and to engage in explorative trial-and-error learning. Results indicated that these conditions nurtured and empowered participants. In addition, obstacles such as low self-efficacy, low confidence, and negative attitudes to technology were substantially reduced. Participants developed new approaches to learning and experienced personal growth through reflective journals that documented their learning journey. (Contains 2 figures.)