This article presents different variants of the clinical course of complications of adrenal tumors with rupture and formation of retroperitoneal hematomas, depending on the morphological characteristics of the neoplasms. The first clinical case described a 38-year-old patient with adrenocortical carcinoma of the left adrenal gland up to 8 cm in size, complicated by rupture with the formation of a retroperitoneal hematoma with a volume of 2800 cm3 , simulating a giant extraorgan retroperitoneal tumor with anemia and cachexia. After surgical treatment and stabilization of the condition, the patient is referred for chemotherapy with a positive outcome. The second case is about a 21-year-old patient with undiagnosed pheochromocytoma, who had a tumor rupture with hemorrhage and the development of acute symptoms against the background of the start of antihypertensive therapy. After the retroperitoneoscopic adrenalectomy, the condition stabilized. The third case is about the experience of observing a 45-year-old patient with myelolipoma up to 6.4 cm, complicated by a previously suffered retroperitoneal hematoma, in whom surgical treatment was not performed due to the presence of end-stage chronic kidney disease and stable tumor condition.