Many researchers argue that information systems (IS) can play an important role in supporting organizational knowledge application. However, recent IS research indicates that knowledge management systems (KMS) often fail when implemented in the knowledge work practice of contemporary organizations. While KMS maintenance has been recognized as an important IS research area, imbalance between the desire for accurate content and the workload required to achieve this still appears to be a critical issue, resulting in systems of little use for organizations in their knowledge application processes. Driven by the ambition to contribute recommendations for how to integrate KMS with everyday knowledge work, we use general lessons learned from development of groupware applications as a theoretical lens to analyze empirical experiences from three implemented and evaluated KMS. Targeting the KMS maintenance challenge, our recommendations extend earlier IS research on the implementation and use of knowledge work support systems. On a practical level, our recommendations assist KMS developers in attempts to bridge the knowing-doing gap in organizations where individual members do not know or know of each other and the organization as a whole does not know what it knows.