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Background: Despite their essential role in language concordant patient care, medical interpreters do not routinely receive training focused on difficult conversations and may not feel comfortable interpreting these encounters. Previous studies, while acknowledging the need for increased support, have provided limited strategies targeted at enhancing interpreter training and improving interpreter comfort levels in difficult conversations. Methods: Fifty-seven in-person medical interpreters providing services at our quaternary and community hospitals completed a 21-question mixed-methods survey regarding their comfort levels and experiences surrounding serious illness conversations. Results: Most medical interpreters reported being uncomfortable interpreting conversations surrounding difficult diagnosis, poor prognosis, and/or end-of-life. Nearly all respondents (98%) indicated that pre-meetings and/or debriefings with the medical team are helpful, yet only 25% reported frequent participation in these meetings. Conclusions: Our study highlighted the significant variability in medical interpreter training as well as ranging comfort levels in interpreting difficult conversations. Medical providers should not presume that interpreters are instantly prepared for these encounters. Current findings call for novel training opportunities specific to medical interpreters and difficult dialogues, as well as improved adherence of interprofessional pre-meeting/debriefings when serious news is discussed.