Introduction: ‘Fit’ refers to an applicants' perceived compatibility to a residency programme. A variety of structural, identity-related and relational factors contribute to self-assessments of fit. The 2021 residency recruitment cycle in the USA was performed virtually due to the COVID-19 pandemic. Little is known about how video-interviewing may affect residency applicants' ability to gauge fit. Methods: A multidisciplinary, anonymous survey was distributed to applicants at a large academic institution between rank order list (ROL) certification deadline and Match Day 2021. Using Likert-type scales, applicants rated factors for importance to ‘fit’ and their ease of assessment through video-interviewing. Applicants also self-assigned fit scores to the top-ranked programme in their ROL using Likert-type scales with pairs of anchoring statements. Results: Four hundred seventy-three applicants responded to the survey (25.7% response rate). The three most important factors to applicants for assessment of fit (how much the programme seemed to care, how satisfied residents seem with their programme and how well the residents get along) were also the factors with the greatest discrepancy between importance and ease of assessment through video-interviewing. Diversity-related factors were more important to female applicants compared with males and to non-White applicants compared with White applicants. Furthermore, White male applicants self-assigned higher fit scores compared with other demographic groups. Conclusion: There is a marked discrepancy between the most important factors to applicants for fit and their ability to assess those factors virtually. Minoritised trainees self-assigned lower fit scores to their top-ranked programme, which should raise concern amongst medical educators and highlights the importance of expanding current diversity, equity and inclusion efforts in academic medicine.