PURPOSE Conversations about personal values and goals of care (GOC) at the end of life are essential in caring for patients with advanced cancer. However, GOC conversations may be influenced by patient and oncologist factors during transitions of care. METHODS We electronically administered surveys to medical oncologists of inpatients who died from May 1, 2020, to May 31, 2021. Primary outcomes included oncologists' knowledge of inpatient death, anticipation of patient death, and recollection of GOC discussions. Secondary outcomes, including GOC documentation and advance directives (ADs), were collected retrospectively from electronic health records. Outcomes were analyzed for association with patient, oncologist, and patient-oncologist relationship factors. RESULTS For 75 patients who died, 104/158 (66%) surveys were completed by 40 inpatient and 64 outpatient oncologists. Eighty-one oncologists (77.9%) were aware of patients' deaths, 68 (65.4%) anticipated patients' deaths within 6 months, and 67 (64.4%) recalled having GOC discussions before or during the terminal hospitalization. Outpatient oncologists were more likely to report knowledge of patient death ( P < .001), as were those with longer therapeutic relationships ( P < .001). Inpatient oncologists were more likely to correctly anticipate patient death ( P = .014). Secondary outcomes revealed 21.3% of patients had documented GOC discussions before admission and 33.3% had ADs; patients with a longer duration of cancer diagnosis were more likely to have ADs ( P = .003). Oncologist-reported barriers to GOC included unrealistic expectations from patients or family (25%) and decreased patient participation because of clinical conditions (15%). CONCLUSION Most oncologists recalled having GOC discussions for patients with inpatient mortality, yet documentation of serious illness conversations remained suboptimal. Further studies are needed to examine barriers to GOC conversations and documentation during transitions of care and across health care settings.