This chapter is motivated by one simple question: Why do so many knowledge management systems (KMS) fail when implemented in organizational knowledge work practice? Indeed, imbalance between the desire for accurate content and the workload required to achieve this still appears to be a critical issue, resulting in KMS of little use for organizational members. Hence, KMS maintenance is an important research subject. With the objective to contribute recommendations for how to integrate KMS with everyday knowledge work, we apply general lessons learned from development of groupware applications as a theoretical lens to analyze empirical experiences of three implemented and evaluated KMS. Theorizing the relationship between the recommendations developed and extant KMS design theory, the chapter offers implications for IS research and practice.