In a world highly dependent upon information systems (IS), continuous technological and organisational changes affect, often in hidden ways, organisations’ habitual performance, thus increasing the likelihood of crisis and breakdowns. While IS and management literature provide a variety of approaches and methods to deal with these changes, especially IS changeovers and upgrades, we still fail to recognise underlying mechanisms and forces determining their success or failure. Through the examination of a recent crisis in a University, following a changeover in Student IS operations, in this paper we propose a sense-making perspective to explain how and why the crisis occurred. Moreover, we demonstrate how a sense-making view of knowledge management provides a framework for understanding and predicting critical issues in IS changeovers.