Organizational decisions of the future may include social, environmental, and economic concerns, and be much more “wicked” [Policy Sciences, 4 (1973) 155], complex and interconnected than those of the past. Organizations and their decision support systems must embrace procedures that can deal with this complexity and go beyond the technical orientation of previous DSS. Singerian inquiring organizations [Australian Journal of Information Systems, 6 (1) (1998) 3; http://www.cba.uh.edu/˜parks/fis/fis.htm (1998); Proceedings of 3rd Americas Conference on Information Systems, Indianapolis, August 1997, p. 293; Proceedings of the 1999 Meeting of the America's Conference on Information Systems, Milwaukee, August 1999; Special Issue of Information Systems Frontiers on Philosophical Reasoning in Information Systems Research (in press)], based on Churchman's [The Design of Inquiring Systems: Basic Concepts of Systems and Organization, Basic Books, New York, NY, 1971] inquiring systems and Mitroff and Linstone's [The Unbounded Mind: Breaking the Chains of Traditional Business Thinking, Oxford Univ. Press, New York, 1993] unbounded systems thinking (UST), are designed to deal with wicked decision situations. This paper discusses DSS and knowledge management in Singerian organizations and calls for a new decision-making paradigm for DSS.