This volume of Annals of Information Systems will recognize the twentieth anniversary founding of the International Society for Decision Support System (ISDSS) with documenting some current best practice in teaching and research and formulate the next twenty years in the field of decision support systems. This volume is intended to complement existing literature by offering an outlet for DSS thoughts and research are particularly suited to the theme that describes the next twenty years in the field of decision support. Several subthemes are planned for volume. Tone of this volume is one of enthusiasm for the potential for future contributions in the field of DSS, the contribution which must incorporate an understanding of what has been achieved in the past, build on best practices today, and will be integrated into future decision-making practices. The main question posed by this volume are: What will the information-based decision support systems require twenty years? What best practice teaching in the area of decision support that can be used to disseminate best progress DSS knowledge to students and practitioners?