Despite recent interest in studying information system habits, our understanding of how these habits develop and operate in an organizational context is still limited. Within organizations, IS habits may develop over long periods of time and are typically embedded within larger, frequently practiced, higher-level work routines or task sequences. When new systems are introduced for the purpose of at least partially replacing incumbent systems, existing IS habits embedded in these routines may inhibit adoption and use of the new systems. Therefore, understanding how work-related IS habits form, how they enable and inhibit behavior, and how they can be disrupted or encouraged requires that we examine them within the context of organizational and individual level work routines. The current study integrates psychology and organizational behavior literature on cognitive scripts and work routines to examine IS habits as they occur embedded within larger, more complex task sequences. The objective of the paper is to contribute to the IS habit literature by (1) situating IS habits within the context of their associated work routines and task sequences, and (2) providing a theoretical understanding of how incumbent system habits can be disrupted, and how development of new system habits can be encouraged, within this context. We draw from extant research in psychology, organizational behavior, and consumer behavior to offer propositions about context-focused organizational interventions to break, or otherwise discourage, the continued performance of incumbent system habits and to encourage the development of new system habits. Specifically, our theoretical development includes script disruption techniques, training-in-context, and performance goal suspension as organizational interventions that disrupt incumbent system habits. We further theorize how stabilizing contextual variables associated with modified work routines can facilitate the development of new system habits. The paper concludes by discussing the importance of combining intervention strategies to successfully disrupt incumbent system habits and encourage development of new system habits and thus facilitate adoption of new systems.