Drawing on Bourdieu’s (1990, 1998, 2000) socio-cultural theories, this article explores the construction of technological expertise amongst a heterogenous group of New Zealand teenagers, specifically in regard to their home computer use, which for many of them is their primary site of leisure. The qualitative study involved observations and interviews with eight teenagers aged 13–17. All the participants considered themselves to be technological experts, and their peers and/or their family supported this self-description. This article examines differences between the concepts and value of learning, expertise, and technology, and how they are valued differently between generations. After discussing the habitus (dispositions) prevalent in the field of out-of-school leisure of teenage experts, the notion that the participants are addicted to their computers is explored. This article highlights a tension regarding how practice in the field is conceptualised differently by digital insiders and digital newcomers, and discusses some implications for educators.