The frameworks underlying the Semantic Web have developed and matured greatly over the last years. However, uptake has been patchy, with the majority of SW use based around a small number of popular applications. User testing with SW–based projects highlights a number of issues that may contribute to this effect; principally, these relate to gaps between the user’s mental model and formalism. Similar problems appear in non–SW developments with a strong reliance on a complex data model. Such problems include semantic drift and overload, and the provision of inaccurate or incomplete data. Working from a case study, this paper discusses difficulties with capturing real–world semantics in a large–scale collaborative environment. A preliminary model of user behaviour with respect to shared establishment of semantics, from socially shared cognition, is discussed. We conclude by discussing some possible features of a “discount” model of the Semantic Web, designed to accomodate diverse communities of users, with reference to examples taken from the “small–S” Semantic Web, microformats and free–text tagging.