This paper motivates a comprehensive methodological framework for dealing with some aspects of real-world complexity in information system analysis and design. By complex application problem, we mean a problem that cannot be solved by the current technology in the way that it is perceived and analyzed by application domain specialists. The paper focuses on a motivating case study, the analysis of constraint violations in database management at the Belgian agency for social security. We then re-interpret practices and their problems in terms of current information system technology. Recommendations are derived both for suitable developments of the technology, that would allow a better treatment of complex real-world problems, and for methodological improvements in data management practices in the application domain, that would take better advantage of the current technology.