In information systems (IS) research, top management support is typically seen as an exclusively positive phenomenon that is key to any successful digital transformation including IS implementation and associated organizaational, operational and startegic chnage. . Surprisingly, this view contrasts with the findings of organization studies research, which reveal a “dark side” of top management support. We propose that this chasm in the research findings may result from: (1) IS research taking a single-sided view of a dialectic phenomenon; or (2) IS implementation being a phenomenon within which top management support can only ever play a positive role. This study examines these propositions by employing a hermeneutical analysis of a published case study on the implementation of an enterprise resource planning (ERP) system. The findings support the first proposition, revealing that senior management “hyperopia” and overconfidence could lead to significant operational confusion and a costly implementation. The study contributes to IS research by revealing that the style and approach of top management support are key to determining the impact of that support and whether it is positive and/or negative. It also extends management research on the dark side of top management to the domain of IS implementation and organizational change, in addition to providing a thorough application of hermeneutical analysis.