Healthcare providers often underestimate patients’ pain, sometimes even when aware of their reports. This could be the effect of experience reducing sensitivity to others pain, or distrust toward patients’ self-evaluations. Across multiple experiments (375 participants), we tested whether senior medical students differed from younger colleagues and lay controls in the way they assess people’s pain and take into consideration their feedback. We found that medical training affected the sensitivity to pain faces, an effect shown by the lower ratings and highlighted by a decrease in neural response of the insula and cingulate cortex. Instead, distrust toward the expressions’ authenticity affected the processing of feedbacks, by decreasing activity in the ventral striatum whenever patients’ self-reports matched participants’ evaluations, and by promoting strong reliance on the opinion of other doctors. Overall, our study underscores the multiple processes which might influence the evaluation of others’ pain at the early stages of medical career.