This paper investigates the architecting of learning organizations in the study of information systems (IS) design. Specifically, we emphasize the role of a suitable organizational context in the development of various information systems supporting the specific requirements of today’s organizational dynamics. The paper describes our initiatives in systems thinking to substantiate IS education in terms of expositing the practitioners’ challenge to tailor the design of appropriate IS’s 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 the importance of identifying the locus of transformation so as to ensure the fulfillment of organizational goals. This is done by presenting our 4-R framework to direct the IS efforts in pursuit of the learning organization ideal, and by discussing the collaboration required of the IS teams to facilitate the incremental transformation into a learning organization through a concerted effort in organizational modeling.