Health information systems (HIS) and clinical workflows generate medication errors that affect the quality of patient care. The rigorous evaluation of the medication process’s error risk, control, and impact on clinical practice enable the understanding of latent and active factors that contribute to HIS-induced errors. This paper reports the preliminary findings of an evaluation case study of a 1000-bed Japanese secondary care teaching hospital using observation, interview, and document analysis methods. Findings were analysed from a process perspective by adopting a recently introduced framework known as Human, Organisation, Process, and Technology-fit. Process factors influencing risk in medication errors include template- and calendar-based systems, intuitive design, barcode check, ease of use, alert, policy, systematic task organisation, and safety culture Approaches for managing medication errors also exert an important role on error reduction and clinical workflow.