Purpose. We investigate one specific case in which the transformation from a HTML to an XML-based organizational Web environment was pursued through portal server technology. The aim is to understand the dynamics of negotiating functionality when there are so many more options available than merely shifting to XML. Method. We report the early phases of a longitudinal study in which various members of the organization, as well as developers, are repeatedly interviewed in order to map changing insights and attitudes. The array of misunderstandings observed is discussed through Wittgenstein's concept of language games. Results. Ordinary users are seen to have substantial difficulties in understanding and discussing the new technology. Their emphasis is on sophisticated applications that developers were unable to implement in time for the launching of the portal. Members of the project group and the steering group also evidenced difficulties in communicating on the key language games on motives, priority, features, implementation and timeline. Originality. The use of language games, and a longitudinal qualitative study, supplies an in-depth view of complications connected to the implementation of information systems that involves existing information practices.