Teaching and assessing doctor-patient communication has become a priority in medical education. This pilot study evaluated resident physicians' perceptions of teaching and assessing doctor-patient communication skills related to pain management using a web-based format. Fifty-nine resident physicians completed four doctor-patient clinical encounters conducted with standardized patients (SPs) connected remotely via SKYPE. Quantitative and qualitative program evaluation data included residents' responses to Post-Exercise Surveys and their comments during focus group sessions. The investigation provided valuable information, especially regarding SP feedback received, the technology used and possible uses of this type of assessment in medical education. Future studies will focus on refinements in technology and alternative topics for use in remote clinical encounters. Appended to the presentation are: (1) Case Introduction for the Chest Pain Case; (2) Chest Pain Checklist; (3) Doctor-Patient Global Communication Assessment; (4) Doctor-Patient Communication Self-Assessment; (5) Technology Report; and (6) Responses to Physician Post-Exercise Survey.