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Electronic medical record (EMR) has gained increasing attention in the healthcare industry worldwide. Unfortunately, the adoption rate has been slower than what healthcare practitioners and IT professionals would expect. While various issues have recently been raised concerning hospitals’ and physicians’ EMR challenges, this research proposal specifically focuses on cultural differences in those healthcare organizations’ and practitioners’ EMR experiences. More specifically, a four-layer cultural framework is proposed and discussed. In additional to traditionally perceived national and organizational cultures, the framework further distinguishes institutional and group cultures that might also interact with other cultural elements and healthcare organizations’ EMR experiences. Six organizations situated in three culturally contrasting countries with comparative external environments, business purposes, managerial values, IT services, and organizational sizes are selected as potential study sites. An interpretive case study is further proposed to help investigate complex interactions involved in this research phenomenon. With a more comprehensive perspective on cultural effects and emerging nature of EMR systems, empirical research contribution, upon the project’s completion, is thus anticipated.