Knowledge management is an ever researched area in the discipline of information systems. Though the terminology might change with the waves of fashion, how information systems can support the multiple dimensions of knowledge management is an underlying theme in many streams of research. This article examines literature on knowledge management in order to synthesize a number of key challenges, which emerge from a multidimensional and boundary-spanning view on knowledge management. Six interrelated issues attempt to explain some of the essential aspects of knowledge in the organizational context: these issues are (1) standardization of processes, structures, and systems, (2) contextualization, (3) invasiveness in natural ways of working, (4) strategic alignment, (5) intelligence, and (6) cultural environment.