This book constitutes the refereed proceedings of the Second International Conference on Decision Support Systems Technology, ICDSST 2016, held in Plymouth, UK, May 23-25. The theme of the event was "Decision Support Systems Addressing Sustainability & Societal Challenges", organized by the EURO (Association of European Operational Research Societies) working group of Decision Support Systems (EWG-DSS). The 14 full papers presented in this book were selected out of 51 submissions after being carefully reviewed by internationally experts from the ICDSST 2016 Program Committee and external invited reviewers. The selected papers are representative of current and relevant research activities in various areas of decision support systems, such as sustainability and societal challenges; risk management and project portfolio management; business intelligence and knowledge management; and technologies to improve system usability.