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To characterize features of medical student exposure to difficult conversations during a neurology core clerkship.This was a cross-sectional concurrent nested mixed methods study, and all students rotating through a required neurology clerkship between 2014 and 2015 were enrolled. Data collection included an electronic communication tracker, baseline and end-of-clerkship surveys, and 4 facilitated focus groups. Students were asked to log exposure to patient–clinician conversations about (1) new disability, (2) poor prognosis, (3) prognostic uncertainty (4), terminal diagnosis, and (5) end-of-life care.A total of 159 students were enrolled and 276 conversations were tracked. Most (70%) students observed at least 1 difficult conversation, and conversations about poor prognosis, new disability, and prognostic uncertainty were most commonly logged. At clerkship end, most students (87%) desired additional bedside training in communication skills. Exposure to one of the predefined conversation types did not improve student perceived preparedness to lead difficult conversations in the future. In focus groups, students noted that the educational value of observation of a difficult conversation could be optimized with preconversation planning and postconversation debriefing.Difficult conversations are common in neurology, and represent a valuable opportunity to provide communication skills training on the wards. Future curricula should consider ways to leverage these existing opportunities to enhance communication skills training.