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Knowledge management is an increasingly important source of competitive advantage for organizations. Knowledge is a renewable, re-usable and accumulating asset of value to firms that increases in value with employee experience and organizational life. Knowledge embedded in the organization's business processes or the employee's skills are assets are generally hard to discern, accumulate and replicate by competitors. It provides the firm with unique capabilities or resources to deliver customers with a product or service. In contrast, as we undertake electronic commerce, customer interfaces and business strategies generally become more visible to competitors. Thus, the organization's capacity to effectively accumulate and leverage knowledge assets better than its competitors becomes a key source of competitive differentiation. As firms become more knowledge intensive, more effort is being expended on knowledge management (KM). While much progress has been made on designing IS to support decision making, the art and design of KM systems to preserve, index, formalize and leverage knowledge in organizations is still new. This paper reviews approaches to knowledge management support systems (KMSS) and proposes the need to design systems that carefully map their features to target organizations and user groups. It illustrates Annotate as a specific KMSS designed to support the knowledge management of document collections in federated organizations which lack common vocabularies and central authority.