This study deals with the problems users encounter in their daily work with computers and the typical practices that they employ. Sixteen daily computer users were interviewed about their habits and problems that they encountered during document classification and retrieval. For both these areas, we provide an overview of identified user practices and a citation-based analysis of the problems users encountered, including those related to the use of the screen real estate (the actual desktop). Two types of problems were identified: (1) Problems that concern the actual use of the system installed on the computer. (2) Problems that arise when people realise that they are using a system that does not allow for the desired work or organizational functions sought. We were able to show that skill continues to be an important factor with respect to the ease of using today’s systems. We suggest the following necessary improvements for the evolution of personal information systems: A storage facility that represents the user’s view of information; replacing pure technical file metadata with more user-friendly attributes; and introduction of annotations as a new information type.