Attending physicians need to supervise resident physician sign-outs in order to ensure patient safety. In one survey study, 59% of resident physicians reported at least one case of harm to one of their patients due to communication issues during sign-outs in their last rotation. In prior research, we identified ‘best practices’ for sign-outs used by attending physicians. For the outgoing physician, communication strategies improve the informativeness, structure, and coverage of the information. For the incoming physician, communication strategies focus on minimizing interruptions, active listening, and assertively questioning the accuracy of contentious decisions. These may include diagnoses, treatment plans, and prognoses. Real-time monitoring of four teams of resident physicians conducting sign-outs simultaneously is extremely difficult for attending physicians without computerized decision support. In this study, we examined the impact of providing automated highlights of sign-out transcripts on the ability to judge the quality of the sign-out. A between-subject design was employed to compare performance with a system displaying four transcripts of sign-outs simultaneously vs. one with the automated highlights on the transcripts. Study participants were 16 fourth-year medical students. Hypothesized benefits of the computerized support on performance and efficiency were not detected. One explanation is that the participants did not understand or agree with the best practice communication strategies, which were used in the design of the highlighted information. Nevertheless, study participants without the computerized support were more likely to judge the supervisory task as not able to be performed safely (p<0.05). All study participants reported that they would be more comfortable performing the task if they were already familiar with the patients (p<0.05). Implications of the study findings include design revisions to the computerized support and the need to provide training on best practices for software assisted sign-outs.