The papers included in this special issue of Decision Support Systems are drawn from the second annual pre-ICIS SIG DSS workshop. The papers describe the efforts of DSS researchers to push the boundaries of DSS research. The papers cover a range of topics but they have a common theme: providing decision support in increasingly complex decision-making situations. All of the papers are concerned with addressing a core characteristic of truly complex problems: the problems have different characteristics when viewed from different perspectives. This paper describes the motivation for the workshop and outlines potential research areas. It also provides a summary of the papers in this issue.