In their qualitative study of Johns Hopkins medical student experiences with challenging patient encounters, Willis and colleagues illustrate an important knowledge gap in medical student education. Among their findings, Willis’s team reports that delivering bad news was a frequent challenge faced by medical students when speaking with patients. Furthermore, it appeared that over time (from second to fourth years of medical school), engaging in these tough conversations was no easier. In fact, over half of respondents indicated a lack of knowledge and experience in these difficult encounters, a major limitation of our education process. In response, Amin and Ullah reflect that the trainee–patient dynamic tends to improve with time and mentorship. Both the commenters and the investigators of this study agree that the challenges faced by medical students change with time because experience and confidence grow. However, the fact that trouble with difficult conversations persists throughout the last year of graduation highlights the need for continued mentorship, or a focused longitudinal curriculum on communication skills, to cultivate this important physician attribute.