Leiomyomata are the most common uterine neoplasm, occurring in at least 20–25% of all reproductive-aged patients. The prevalence of uterine myomas among pregnant patients ranges from 0.1 to 3.9% and is likely to increase as more patients delay childbearing until later in life. Pain is the most reported complication of fibroids in pregnancy, with approximately 10–30% of patients with uterine fibroids developing pain during pregnancy. Acute pain episodes can be severe enough to warrant hospitalization and analgesia in certain instances and therefore present a significant complication for pregnant patients with fibroids. Pain from uterine fibroids during pregnancy is thought to be due to red degeneration, which is defined as hemorrhagic infarction of a previously hyalinized myoma caused by ischemic necrosis. Although this was previously thought to be caused by rapid fibroid growth during pregnancy, recent studies suggest that these painful episodes appear to be unrelated to absolute fibroid size. In this case we will explore the pathophysiology of degenerating fibroids in pregnancy including the natural course of uterine fibroids in pregnancy, typical presentation, causes, and treatment options.