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Purpose: To report a challenging case of spontaneous hyphema in the setting of prone positioning for COVID-19 pneumonia. Observations: A previously healthy patient was concomitantly diagnosed with acute myelogenous leukemia (AML) and COVID-19 infection. During his hospitalization he required intubation and prone positioning. Following change from prone to supine positioning, he was noted to have developed a large unilateral spontaneous hyphema. Conclusions and Importance: We present a challenging case of spontaneous hyphema due to a hematologic malignancy in the setting of prone positioning for COVID-19 pneumonia.