This paper argues that the complementary perspectives of systems-rationalism and segmented-institutionalism (Kling, 1980) can be used to inform requirements analysis for information technology (IT). This paper addresses the issue of informing requirements analysis by using these complementary perspectives to examine expectation failures of a recent attempt to provide technology- mediated post-secondary education, the Western Governors University (WGU). These expectation failures provide an opportunity to explore why the factors contributing to these failures were overlooked in the process of requirements analysis for WGU.