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In studying strategic information systems (IS) alignment, it is important to examine the associated processes over time rather than view alignment as an isolated event. This article focuses on how organizations undergo a series of interdependent changes in business strategy and IS strategy to increase the alignment between them. Based primarily on detailed case studies of changes over long time periods in three organizations, the research suggests that this process of adaptation and change, which allows alignment to occur, is more complex than previously believed. Although efforts to achieve alignment between IS and the business do sometimes succeed, they often go astray. There are three such potentially problematic trajectories - excessive transformation, paradoxical decisions, and uncertain turnarounds. This article identifies some factors explaining why organizations might pursue these problematic trajectories and offers some suggestions for avoiding them.