End user resistance to information systems (IS) adoption and use is a key concern for both research and practice. To date, behavioral models of IS use have focused primarily on the conscious decisions made by users in choosing to adopt or continue using a particular system. Only recently have researchers begun to explore the unconscious role of habit in influencing IS usage. The current research deviates from prior studies that focus on habits role in superseding intentions to predict continued use of a system, by viewing habit with an existing system and the resulting inertia as inhibitors of technology acceptance as it pertains to a new system. Our research follows the three-manuscript model. In the first manuscript, we situate habitual IS usage behaviors within the context of their associated work routines and task sequences, and provide a theoretical understanding of how habits develop and how they can be disrupted within an organizational context, acknowledging their dual facilitating and inhibiting effects: that is, habitual use of an existing system encourages continued usage of the system but discourages adoption of new systems. In the second manuscript, we focus on the development of a theoretically based and thoroughly validated instrument for measuring habitual IS use in an organizational work environment. In the final manuscript, we use the newly-developed measure to address the negative impacts of IS habits on adoption of newly introduced systems, by situating habit and its consequence, inertia, in a nomological network of technology acceptance constructs and hypothesizing their effects on behavioral beliefs and intentions. As such, we extend our theoretical understanding of the role of habit in technology acceptance, and lay the foundations for further study of organizational interventions to both break undesired IS usage habits and encourage the development of new ones.