This contribution discusses challenges to lexicography created by the new computer, information and communication technologies and techniques. It argues that the current transition period is full of paradoxes and that the main problem seems to be the subjective factor, i.e. the ability to adapt fully to the new technologies and get rid of old habits and ways of thinking. The article provides some examples of how the current challenges can be approached in terms of databases, user interfaces and other tools and techniques to assist the compilation and presentation of online dictionaries. In this context, it also calls for the opening of new areas of research into the empirical basis of dictionary production. The contribution defends the need for a lexicographical theory and a theory-based methodology which should be combined with visions on how lexicography and technology can be integrated in an ever ascending spiral that constantly provides new solutions to both old and new problems.