Patient sign-out is a mechanism for transferring information, responsibility, and/or authority from one set of caregivers to another. Little research has addressed what information should be communicated during sign-out and how sign-out should be conducted and evaluated. As hospital residents conduct many sign-outs and have limited time in general, targeted web-based training and evaluation have the potential to enhance Graduate Medical Education. However there are no web-based training systems for this very important skill. This paper presents the operational concept and system requirements for a web-based sign-out training system. It discusses an initial functional prototype. Results of a heuristic evaluation and an assessment of areas for improvement are presented.