This paper sets out to problematise generational categories such as "Power Users" or "New Millennium Learners" by discussing these in the light of recent research on youth and information and communication technology. We then suggest analytic and conceptual pathways to engage in more critical and empirically founded studies of young people's learning in technology and media-rich settings. Based on a study of a group of young "Power Users", it is argued that conceptualizing and analyzing learning as a process of patchworking can enhance our knowledge of young people's learning in such settings. We argue that the analytical approach gives us ways of critically investigating young people's learning in technology and media-rich settings, and study if these are processes of critical, reflexive enquiry where resources are creatively re-appropriated. With departure in an analytical example, the paper presents the proposed metaphor of understanding learning as a process of patchworking and discusses how we might use this to understand young people's learning with digital media. (Contains 1 figure and 2 tables.)