Software and Information Systems (IS) documents are a common product of large IS development e orts. These documents are produced and consumed through a variety of documentation processes. These processes involve developers and users working within complex organizational settings, as well as with the focal system under development. These organizational settings facilitate and constrain IS documentation and development e orts in complicated ways. Accordingly, we present, analyze, and compare cases from eld studies of three di erent IS development e orts in a large industrial corporation. Based on these studies, we identify a new set of variables and hypotheses that we believe represent a more plausible set of requirements for IS documentation products and processes in di erent organizational settings. In this regard, we utilize the concept of viewing IS documentation requirements as hypotheses to be tested, re ned, or refuted.