Objective: To investigate residents' experiences recording and receiving feedback on a challenging video of a patient encounter. Methods: We used a qualitative design with first year residents who took part in a mandatory communication skills course in which all participants were asked to bring a challenging video of a patient encounter. The methods consisted of brief reflection texts and focus groups related to their perspectives on the use of challenging videos. Results: 106 residents wrote brief reflection texts, and 13 residents participated in four focus groups. Residents mainly expressed positive experiences with the challenging video exercise. Residents reported that the pressure to perform was felt to be less than on previous teaching sessions because the focus was on choosing an encounter which was less than perfect. They also reported that they appreciated the opportunity to see that other doctors were not performing optimally. Conclusion: The use of challenging videos as a teaching method for communication skills was experienced as encouraging by residents and facilitated enhanced learning. Innovation: We recommend adding more focus on challenging situations in video review. This could support learning by providing what our participants found to be a less daunting learning environment.