Background and Objectives: Anesthesiologists come into contact with patients under palliative care in different clinical settings. They also routinely encounter these patients in their primary field of work, the operating room. Patients receiving palliative care who are scheduled for surgery will pose unique challenges in perioperative management, often presenting with advanced disease and with different psychosocial and ethical issues. This study aims to evaluate whether anesthesiologists without specialty training in palliative medicine will spot perioperative challenges presented by patients under palliative care and address them adequately. Materials and Methods: In this study, we simulated a preoperative anesthesiological interview using standardized patients and anesthesiologists (specialists as well as trainees). The standardized patients were asked to represent a patient under palliative care in need of surgery because of a mechanical ileus. We conducted 32 interviews, dividing the anesthesiologists into two groups. In one group, the standardized patients were instructed to address four problems, i.e., use of a port catheter for anesthesia, nausea and vomiting, pain medication, and an advance directive including a limitation of treatment (DNR-order). In the other group, these problems were also present, but were not actively addressed by the standardized patients if not asked for. The interviews were recorded, transcribed, and then analyzed. Results: In most cases, the medical problems were spontaneously identified and discussed. In only a few cases, however, was a therapy recommendation made for improved symptom control. The advance directive was spontaneously discussed by only 3 of the 32 (9%) anesthesiologists. In another 16 cases, the advance directive was discussed at the request of the standardized patients. The limitation of treatment stayed in place in all cases, and the discussion of the advance directives remained short, with an average duration of just over 5 min. Conclusions: In this study, the complex problems of patients under palliative care are not sufficiently taken into account in a preoperative anesthesiological interview. To improve treatment of the medical problems, therapists who have palliative medicine expertise, should be involved in the perioperative medical care, ideally as a multi-professional team. The discussion about perioperative limitations of treatment should be held beforehand, for example, as part of a structured advanced care planning discussion.