We theorize about the strategic alignment of computing with organizational mission, using the Commonwealth of Pennsylvania's efforts to pursue digital government initiatives as evidence. To do this we draw on a decade (1995-2004) of changes in Pennsylvania to characterize how a state government shifts from an organizational to an enterprise perspective regarding computing. We document and analyze the strategic and operational aspects of a series of information and communications technology (ICT) planning efforts to highlight the nature and roles of strategic alignment used to achieve this transition. Findings from this analysis mark the importance of combining several approaches to strategic planning regarding the adoption and application of ICT. (Contains 1 figure and 3 tables.)