The strategic use of IS and the alignment of IT with business needs are important managerial issues that need to be addressed if optimal organizational performance is to be achieved. IS research has proposed models to optimize the impact of IS investment on organizational performance. The Strategic Alignment Model (SAM) proposed by Henderson and Venkatraman is the most well-known and widely used of these models. However, 20 years on, there remains a significant disparity between the intended contribution of the literature built around SAM and the apparent practical consequences of its application in organizations. In this study, we explain this disparity using a grounded theory stance with a bibliometric and interpretive approach to help us analyze the literature: We use tri-citation analysis (with bibliometric data collected in 2011, and again in 2014) and investigate interpretatively the contents of the texts highlighted by our statistical results. This allows us to show that the research field built around SAM mostly appears not to challenge its basic assumptions and premises, although these may artificially constrain organizational reality and practices. In turn, this leads us to propose an explanation for practitioners’ apparent failures to fulfill SAM’s intended contribution. Beyond our theoretical and methodological contributions, we propose possible theoretical and practical improvements to adapt this model to the current organizational reality.