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Background: Electronic prescribing has been advocated as an important tool for improving the safety and quality of medication use in ambulatory settings. However, widespread adoption of e-prescribing in ambulatory settings has yet to be realized. The determinants of successful implementation and use in these settings are not well understood., Objective: To describe the practice characteristics associated with implementation and use of e-prescribing in ambulatory settings., Design: Multi-method qualitative case study of ambulatory practices before and after e-prescribing implementation., Participants: Sixteen physicians and 31 staff members working in 12 practices scheduled for implementation of an e-prescribing program and purposively sampled to ensure a mix of practice size and physician specialty., Measurements: Field researchers used observational and interview techniques to collect data on prescription-related clinical workflow, information technology experience, and expectations., Results: Five practices fully implemented e-prescribing, 3 installed but with only some prescribers or staff members using the program, 2 installed and then discontinued use, 2 failed to install. Compared to practice members in other groups, members of successful practices exhibited greater familiarity with the capabilities of health information technologies and had more modest expectations about the benefits likely to accrue from e-prescribing. Members of unsuccessful practices reported limited understanding of e-prescribing capabilities, expected that the program would increase the speed of clinical care and reported difficulties with technical aspects of the implementation and insufficient technical support., Conclusions: Practice leaders should plan implementation carefully, ensuring that practice members prepare for the effective integration of this technology into clinical workflow.