This volume of Annals of Information Systems will acknowledge the twentieth anniversary of the founding of the International Society for Decision Support Systems (ISDSS) by documenting some of the current best practices in teaching and research and envisioning the next twenty years in the decision support systems field. The volume is intended to complement existing DSS literature by offering an outlet for thoughts and research particularly suited to the theme of describing the next twenty years in the area of decision support. Several subthemes are planned for the volume. One subtheme draws on the assessments of internationally known DSS researchers to evaluate where the field has been and what has been accomplished. A second subtheme of the volume will be describing the current best practices of DSS research and teaching efforts. A third subtheme will be an assessment by top DSS scholars on where the DSS discipline needs to focus in the future. The tone of this volume is one of enthusiasm for the potential contributions to come in the area of DSS; contributions that must incorporate an understanding of what has been accomplished in the past, build on the best practices of today, and be be integrated into future decision making practices. The primary questions raised by this volume are: What will information systems-based decision support entail in twenty years? What research is needed to realize the envisioned future of information systems-based decision support? How will the teaching of information systems-based decision support change over the next twenty years? What are the best practices of teaching in the decision support area that can be leveraged to best disseminate DSS knowledge advances to students and practitioners?