Objective: The psychiatric clerkship is a stressful experience that influences attitudes toward patients with psychiatric illnesses and influences recruitment into the field. This study focused on medical students' encounters with patients they found troubling or difficult, and whether specific themes regarding their emotional responses could be identified. Methods: Third-year medical students rotating through the psychiatry clerkship participated in a problem patient conference for which they were required to submit a form detailing a troubling encounter that occurred with a patient in the prior week. During the conferences, students discussed these encounters and their responses to them. The encounters were later reviewed and grouped into a set of four themes. Comparisons were made between male and female students, and response to patients at the start and finish of the clerkship. Results: For both male and female students the most common reaction of a problematic encounter was frustration/helplessness, followed by having a strong negative reaction, then identification with patients evoking a disturbing response, and finally feelings of intimidation and fear. There were no gender differences for any of the four categories. The proportion of encounters classified as intimidating/frightening significantly declined from the first half to the second half of the rotation. Conclusion: The problem patient conference is an effective tool to elicit candid concerns regarding the care of psychiatric patients and is an opportunity to empathically address struggles specific to the psychiatric clerkship.