This research develops 45 evaluation criteria for “high-velocity” strategic Decision Support Systems (DSS), and uses them to evaluate 16 popular commercial DSS tools for their fit in supporting “high-velocity” strategic decision-making. Results illustrate the assertion that few currently-available DSS tools support “high-velocity” strategic decision requirements. Based on the findings, the authors recommend further investigation into the importance of configuration on fit between a DSS tool and its environment, and ultimately, recommend designing DSSs that are configurable in the ways outlined herein.