This paper describes a recent activity where scholars from two disciplines met to consider possible systemic causes of repeating failure during a three-decade long IT modernization project in the US government. From the system dynamics perspective, the problem appears to be related to a dynamic and repeating management failure with an embedded project management model. We decided to use a simple project model to develop this perspective. Our initial attempt shows some of the anticipated dynamics of project escalation. More important, though, was the discussion of the problem itself that was launched by the use of a formal model. We believe that this approach has provided insight into how to approach a more focused and grounded analysis of the problem domain.