The paper expands our theoretical and empirical understanding of knowledge flows in heterogeneous information system environments. Through an ethnographic study of a U.S. based teaching hospital it was found that doctors and nurses organize a hodgepodge of information systems, some electronic, other paper-based or wall mounted into circular patterns. The data allows a description of how these cyclical organized systems oscillate between documents that address a broader and narrower configuration of participants, times, places and content. In doing so, organizational members continuously adjust their system use to meet the level of background knowledge held by their collaborators, that is, how intimately their collaborators know the context and the routine work practices at hand. The cyclical organization of information systems does not prevent breakdowns in knowledge sharing. To avert such problems each cycle starts and ends with a dialog and reflection among collaborators.