In this article, the authors focus on scheduling situations. Because of their unstructured nature and hard combinatorial complexity, scheduling situations have always been a predominant application area for decision support systems (DSSes). After setting out the generic characteristics of a DSS, the authors summarize some of their known limitations in scheduling situations. They argue that scheduling situations focus excessively on performance and effectiveness and neglect the potential of human schedulers. The authors then review field studies to understand the way in which humans perform scheduling, demonstrating the importance of cognitive readiness if schedulers are to schedule efficiently. On the basis of design issues and field studies, the authors go on to refine three factors that influence cognitive readiness that therefore need to be taken into account when designing a DSS, namely, adaptability, flexibility, and acceptability. Finally, the authors show how these concepts can be used to assess DSS user interfaces and algorithms from a cognitive readiness perspective.