Organizations routinely process information, make decisions, and implement them. Recent advances in computer and communications technologies have changed the way in which organizations perform these functions. Decision support systems (DSSs) are a major category of tools that an organization utilizes to support and enhance its decision-making activities. Traditionally, organizations are considered to have a predefined and static set of goals. However, in order to stay competitive and survive in today’s dynamic environment, organizations must be able to quickly respond and adapt to changes in their business settings. Such changes could be due to technological advances, growing and changing customer demands, competitive forces, changes in the labor force, environmental and political concerns, societal impacts, security concerns, and others. In recent years, the field of DSS has become more sophisticated to encompass such paradigms as expert systems (ESs), intelligent DSSs, active DSSs, and adaptive DSSs. Artificial intelligence (AI)-based techniques are being embedded in many DSS applications, thus enhancing the support capabilities of the DSS. Such paradigms have application potential in both individual and organizational learning contexts. However, the degree to which current DSSs can support organizational learning has yet to be investigated in depth. This paper examines the learning strategies employed by organizations and DSSs and provides a framework to demonstrate how a DSS can enhance organizational learning.