Electronic Health Records (EHRs) are vital in healthcare, but their usability often varies, affecting user satisfaction and adoption. This study explores the relationship between Work-related Quality of Life (WrQoL) and EHR usability during transitions to updated systems. A comparative analysis of clinical users over two time points found that WrQoL significantly influenced perceptions of usability, highlighting the importance of emotional and contextual factors in technology adoption highlighting the socio-technical aspect of EHR implementation and use. The findings support models emphasizing the role of well-being and organizational context in shaping user experiences. Practical implications include fostering WrQoL through well-being programs, context-aware system design, and user feedback. Future research should investigate causal pathways to enhance EHR usability and healthcare efficiency. This study emphasizes the critical role of user well-being in successful health information system implementation.