When comparing how younger and older internet users search for information, young people often impress by operating Web applications quickly and effortlessly. However, information literacy is not only a question of speed; it is highly dependent on cognitive abilities such as monitoring and regulating the search process. To avoid a general deficiency perspective on older Web users, this study goes beyond the results of Web searching to focus on individual approaches to information problem solving. We conducted ten guided interviews based on two different search tasks the participants (aged 16-77) worked on while thinking aloud. Applying a qualitative content analysis approach, we find that younger participants (aged 16-26) use more productive strategies to collect information, but observed no age-related differences in completing a complex task. The strong task dependence of our results underlines the necessity of teaching regulative search techniques that are suitable for solving unstructured everyday problems in order to ensure that all users can make the most of today’s rich but unstructured information environment.