Objectives This study investigates the effectiveness of a virtual format of an advanced communication skills observed structured clinical examination (OSCE) for senior medical students in comparison to an in-person format. The study also examines the emotional support students experience in the virtual setting. Our analysis was based on quantitative data collected through objective checklists and post-OSCE survey results. Methods The virtual OSCE was a revision of an earlier in-person formative advanced communication skills OSCE for fourth-year medical students. Student performances were assessed by self and peers using objective checklists—the modified Master Interview Rating Scale (mMIRS) and Communication Behavior Checklist (CBC). The mMIRS measured interview process such as avoiding jargon and demonstrating empathy. The CBC examined interview content which included tasks specific to the content of the case. The OSCE was followed by a faculty-led debrief and quantitative survey. The virtual OSCE was conducted in 2021, and the results of the checklists and survey were compared with those collected from two earlier in-person OSCEs. Results Eighty-three students participated in the virtual OSCE. There was no difference in mMIRS scores between the virtual and in-person OSCE. Overall CBC scores were lower in the virtual OSCE compared to in-person ( p < 0.05). Sixty-seven out of 83 (80.7%) students completed the post-OSCE survey. There were no differences between the virtual and in-person OSCE in terms of educational value, whether the OSCE would change the way participants talk to patients, and preparedness to have serious conversations with patients. All respondents somewhat or strongly agreed with feeling emotionally supported during the virtual OSCE. Conclusion The virtual format was a suitable alternative to an in-person, formative, advanced communication skills OSCE for medical students. The virtual OSCE was educationally effective and was met with student satisfaction and a sense of emotional support. Future virtual iterations must ensure adequate instruction on interview content.