This case series describes two patients who underwent Cesarean section complicated by a rectus abdominis sheath hematoma that did not immediately resolve following exploratory laparotomy. One of the patients required an additional procedure by interventional radiology. Both patients had similar presentations. Both were noted to have symptomatic anemia on postoperative day 1 with an acute drop in hemoglobin. This was accompanied by severe abdominal pain and distension on physical exam. Computerized tomography (CT) abdomen/pelvis demonstrated evidence of active bleeding within the anterior abdominal wall musculature. Due to increasing concern for intrabdominal hemorrhage in the setting of an acute abdominal exam, the decision was made to proceed with an exploratory laparotomy. A substantial amount of blood was evacuated from the abdomen with greater than 1500 cc of estimated blood loss in both cases. A Jackson-Pratt drain was placed and had increased output immediately postoperatively. Both patients received blood products. One developed a consumptive coagulopathy. Interventional Radiology was consulted following exploratory laparotomy to consider intravascular embolization of the inferior epigastric arteries, which was eventually performed in one of the cases. The patients were discharged on hospital day 5 in good condition. Rectus abdominis sheath hematomas are a rare complication that can lead to significant postpartum hemorrhage. Prompt recognition and management is vital to avoid significant morbidity and mortality. Algorithms exist to guide treatment and standardize patient care. Despite using sound clinical judgment in line with existing algorithms, both patients had delayed resolution of their bleeding following initial management, requiring additional intervention.