This paper investigates the idea of human activity systems (HAS) appropriate to the characterization of the purposeful human activities behind the design of suitable information systems (IS) support, especially in the context of group-based project work. Specifically, we are interested in the knowledge context of a group of people collaborating in the peculiar scenario of project development. Our discussion describes a traceable framework of information systems development (ISD), which should accommodate the application of soft systems methodology (SSM) that acknowledges the importance of people in organization. The paper situates our discussion in the action research experience of the author conducting a junior core course of Software Psychology, delivered through the pedagogy of problem-based learning (PBL), in our four-year undergraduate program of Software Engineering. We intend to clarify the contextualization of designing IS support in relation to teamwork design. This is done by elaborating the IS design issues through the exposition of the human processes in which, in a specific organizational scenario, a particular group of people can conceptualize their world and hence the purposeful action they wish to undertake. That provides the basis for ascertaining what IS support is needed to undertake the necessary action and how modern information technology (IT) can help to provide that support. We conclude by reiterating the challenge of designing truly relevant HAS systems in which people selectively perceive parts of their world, attribute meaning to what they perceive, make judgment about their perceptions, form intentions to take particular actions, and carry out the action themselves. All these activities carry tremendous connotations in the HAS-based process of IS development for group project work, especially in collaborative project participation.