Older people have successful search strategies for finding practical information in everyday situations but, increasingly, traditional information sources are being supplemented or replaced by web based ones. However, there are wider issues than just making information available if people are to replace existing strategies by new web based ones. In this paper we use three studies on the information usage of older people to explore the issues surrounding why they favour specific search strategy and technology combinations. The studies each investigate different aspects of information search in a natural setting and concern tasks relevant to older people as their lives change: finding egovernment information and planning travel. Results suggest that a variety of measures are important in choice of strategy. Furthermore, interface mechanisms are needed that complement existing strategies, reinforce the existence and crossing of boundaries, and support interactive use of landmarks. q