Organizations expend a great deal of effort managing their information system resources as they try to achieve information systems alignment (ISA), but relatively little is known about the different ways in which alignment changes over time in different organizations or what factors predict which kinds of changes are likely to occur. The purpose of this paper is to examine the factors that predict the patterns of ISA change in entrepreneurial organizations. An in-depth examination of the alignment process was conducted using two retrospective case studies. Continuous Change Theory and Punctuated Equilibrium Theory were used to explore ISA patterns in the two organizations. Longitudinal qualitative and quantitative data from the two organizations were used to compare the predictive ability of the two theories regarding ISA changes over time. Results suggest that two factors, organizational inertia and institutionalism, predict the likelihood of an entrepreneurial organization following one ISA change pattern over another.