This dissertation explores the effects of increased digitization on the evolutionary dynamics of organizational routines. Do routines become more flexible, or more rigid, as the mix of digital technologies and human actors changes? What are the mechanisms that govern the evolution of routines? The dissertation theorizes about the effects of increased digitization on path dependence and interdependence mechanisms, and therefore extends current theory on the evolutionary dynamics of organizational routines by taking into account the effects of three basic phenomena: digitization, path dependence and interdependence. In this dissertation, I use computer-based simulation, grounded with data collected in field interviews, to model the evolution of routines. More specifically, this dissertation models routines as networks of action that are subject to an evolutionary process of random variation and selective retention. To assess the evolution of routine, I introduce the idea of evolutionary "trajectory," which is defined as the product of the "magnitude" of change and the "direction" of change in the networks of action. The dissertation also addresses a foundational issue in the literature on organizational routines. Routines are generally believed to remain stable due to "path dependence." An alternative explanation is that routines may be stable due to "interdependence" among actions, which tends to constrain the sequence in which actions can occur. I have developed a simulation that allows me to test the relative importance of these factors, a question that has never been addressed. By addressing this fundamental issue, I provide a deeper, theory driven explanation of the effects of digitization. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]