A significant degree of customization of medical information technology is required to effectively integrate the promise of IT with the diversity and complexity of medical work. In the absence of such customizations, dissatisfaction and resistance toward the system arise. Indeed, the complexity of the medical work and the inability of software to tailor to the diverse medical practices may explain the limited diffusion of health information systems especially in North America. We study the role of workarounds during an open-source Electronic Medical Record System (EMR) implementation at a medium-size urgent care clinic in a major Canadian city. We found that the technology appropriation process involved the evolving of number of non-trivial workarounds in order to match the EMR to medical work. The emergence of workarounds is conceptualized as a knowledge creation and integration process. This perspective allows us to look at the antecedents and the change dynamics of workarounds in the clinic. Furthermore diverging from the negative view toward workarounds, we discuss the importance of incorporating workarounds during and following system development. The workaround perspective shed the light on how users’ behavior can be channeled into a constructive development effort. This paper contributes by examining the workaround of medical practitioners using an open-source electronic medical record system as well as offering a knowledge perspective for the study of EMR appropriation.