Digital skills are an important aspect of ensuring that all young people are digitally included. Yet, there tends to be an assumption in popular discourse that young people can simply learn these skills by themselves. While experience of technologies forms an important part of the learning process, other resources (i.e., access to technology and support networks) plus clear motivations are required. Through in-depth interviews with 20 young people who are digitally excluded, this paper highlights the kinds of digital skills these young people find problematic, and the reasons why they find developing these skills so challenging. We demonstrate how poor access to technology, limited support networks and their current situation prevent these young people from gaining the experiences they need to support the development of their digital skills; and how lack of experience and inadequate skills limit the extent to which they perceive the internet to be valuable in their lives. These individual experiences, shaped very much by the wider social structure of which they are part, show how young people cannot simply be left to learn digital skills by themselves and that intervention is required to try to address some of the digital inequalities apparent in younger generations.