Implementing health information technology (HIT) into clinical settings is still problematic despite extensive efforts and research. HIT issues are caused by a gap in fit between users and technology. The transition from paper (p) to electronic (e) systems is a key factor in the chasm between users and technology. While a significant body of research exists on behavioral or usability evaluation of HIT, there is far less research that looks how to support the transition from p to e systems. This paper presents a framework of ‘p’ benefits to help us understand why issues occur in the transition from ‘p’ to ‘e’ systems. The framework can help us design and evaluate HIT in a manner that bridges the transition from p to e and helps close the user-technology chasm.