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Uterine leiomyomas are a common benign neoplasm of the female reproductive tract. They are often asymptomatic and can be present during pregnancy without complication. When leiomyomas outgrow their blood supply, the tissue undergoes degeneration. This process is most often seen in pregnancy. A rare complication of this process is spontaneous rupture, which is a surgical emergency often resulting in intra-abdominal leakage, bleeding, and peritonitis. This report describes the case of a 36-year-old White woman (G1P0) at 35 weeks of gestation with a known enlarging anterior fundal leiomyoma with degeneration who presented with worsening abdominal pain and contractions in the setting of gestational diabetes mellitus. Imaging and clinical findings were concerning for rupture of a degenerating fibroid with intra-abdominal fluid leakage. This event resulted in threatened preterm labor. She underwent low transverse cesarean section, resulting in delivery of a viable neonate. Intraoperative findings included a broad-based fundal leiomyoma with a 1.5 cm defect and drainage of degenerative contents. Six months postpartum, the patient had persistent fibroid degeneration requiring robotic-assisted laparoscopic myomectomy. This case highlights the rare but serious complications of leiomyoma rupture in pregnancy and underscores the importance of close monitoring and appropriate surgical intervention for patients with degenerating leiomyomas.