This paper investigates the architecting of information systems (IS) support for learning organizations through the elaboration of typical organizational scenarios for knowledge work. Specifically, our discussion is based on the belief that the design issues of IS support must be situated in the context of social processes in which, in a specific organizational scenario, a particular group of people can conceptualize their knowledge work and hence the purposeful action they wish to undertake. This provides the basis for ascertaining what information support is needed by those who undertake that action, and how modern information technology can help to provide that support. The paper describes our initiatives in systems thinking to substantiate IS education in terms of expositing the importance of soft systems methodology (SSM) in the process of IS design according to the evolving contexts of human activity systems. To realize the various IS services in a learning organization, whose requirements are increasingly innovated over different organizational scenarios, we stress architecting IS support for knowledge work requires attention to the purposeful action which the IS serves, and hence to the meanings which make those particular actions meaningful and relevant to particular groups of people in a particular situation. This is often facilitated by the provision of an important SSM-based enquiry process constantly attended to, and integrated into organizational activities by which IS professionals could learn of the organization’s continual adjustments to its changing world. The paper also brings forth the notion of the learning organization information systems (LOIS) whose design, based on specific organizational scenarios, could only be accomplished through the collaboration between the IS teams and those who truly understand the underlying purposeful actions served.