This paper explores the underlying assumptions that are often made concerning the beneficial impact of the use of Digital Technologies in relation to the motivation for academic work, and related forms of engagement. In particular, these claims are assessed in the context of an overarching concern with the motivational characteristics that are most likely to abet the effective transition of young people from one context to another. In this light, relevant theories of motivation are explored together with an assessment of how they might, together, provide a more productive basis for the development of the role of Digital Technology in assisting the making of effective transitions.