This paper explores, through a short case study, the utility of the Soft Information Systems Technology Methodology (SISTeM) and its expressive and matrix models in supporting evaluation of IS applications as part of a procurement process. In addition the potential of these tools in evaluating RAD based, ‘time-box’, contingency approaches to IS development is examined. This suggests a future research agenda for exploring and further development of SISTeM’s modeling tools in support of the evaluation of compartmentalized information systems development and its resultant organizational benefits.